80703-23-7 ((R)-1,1'-联萘-2,2'-二甲酸,[1,1'-Binaphthalene]-2,2'-dicarboxylicacid, (1R)-)

快速询单

结构式：

(R)-1,1'-联萘-2,2'-二甲酸MOL文件

CAS号：

80703-23-7

中文名称：

(R)-1,1'-联萘-2,2'-二甲酸

英文名称：

[1,1'-Binaphthalene]-2,2'-dicarboxylicacid, (1R)-

分子式：

C₂₂H₁₄O₄

分子量：

342.344166278839

(R)-1,1'-联萘-2,2'-二甲酸(80703-23-7)名称与标识符

名称

中文别名：

(R)-1,1’-二萘-2,2’-二羧酸;(R)-1,1'-联萘-2,2'-二甲酸;

英文别名：

[1,1'-Binaphthalene]-2,2'-dicarboxylicacid, (1R)-;(1R)-[1,1'-Binaphthalene]-2,2'-dicarboxylic acid;(1R)-[1,1′-Binaphthalene]-2,2′-dicarboxylic acid (ACI);(+)-1,1′-Binaphthyl-2,2′-dicarboxylic acid;(R)-1,1′-Binaphthyl-2,2′-dicarboxylic acid;18531-96-9;99827-46-0;1-(2-Carboxy-1-naphthyl)naphthalene-2-carboxylic acid;C1C;SS-4976;1,1'-Bi[2-naphthoic acid];Q27458607;(R)-[1,1'-Binaphthalene]-2,2'-dicarboxylic acid;(S)-1,1'-Binaphthyl-2,2'-Dicarboxylic Acid;1,1 inverted exclamation mark -Binaphthyl-2,2 inverted exclamation mark -dicarboxylic acid;CS-0063408;BDBM50428255;E81102;R-1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID;1,1-Bi(2-naphthoic Acid), (+/-)-1,1'-Binaphthyl-2,2'-dicarboxylic Acid;PD129575;CHEMBL1231559;1-(2-carboxynaphthalen-1-yl)naphthalene-2-carboxylic Acid;1-(2-carboxynaphth-1yl)-2-naphthoic acid;AKOS004903304;SCHEMBL895573;1,1'-binaphthalene-2,2'-dicarboxylic acid;[1,1'-Binaphthalene]-2,2'-dicarboxylic acid;CHEBI:188801;AKOS016006617;CCG-239105;SY243404;(R)-1,1'-Binaphthyl-2,2'-Dicarboxylic Acid;80703-23-7;1,1'-binaphthyl-2,2'-dicarboxylic acid;CS-0091853;(R)-1-(2-carboxynaphthalen-1-yl)naphthalene-2-carboxylic acid;A11490;MFCD00185729;SCF-I2;S-1,1'-binaphthyl-2,2'-dicarboxylic acid;(S)-[1,1'-binaphthalene]-2,2'-dicarboxylicacid;(S)-[1,1'-binaphthalene]-2,2'-dicarboxylic acid;(S)-[1,1 inverted exclamation mark -Binaphthalene]-2,2 inverted exclamation mark -dicarboxylic Acid;

标识符

MDL：

MFCD00185729

InChIKey：

YDZNRNHKJQTGCG-UHFFFAOYSA-N

Inchi：

1S/C22H14O4/c23-21(24)17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22(25)26/h1-12H,(H,23,24)(H,25,26)

SMILES：

O=C(C1C(C2C3C(=CC=CC=3)C=CC=2C(O)=O)=C2C(C=CC=C2)=CC=1)O

(R)-1,1'-联萘-2,2'-二甲酸(80703-23-7)物化性质

实验特性

密度 : 1.380

计算特性

精确分子量 : 342.08920892g/mol
氢键供体数量 : 2
氢键受体数量 : 4
可旋转化学键数量 : 3
同位素质量 : 342.08920892g/mol
重原子数量 : 26
复杂度 : 496
同位素原子数量 : 0
确定原子立构中心数量 : 0
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : 5.1
互变异构体数量 : 无
表面电荷 : 0
拓扑分子极性表面积 : 74.6Å²

(R)-1,1'-联萘-2,2'-二甲酸(80703-23-7)推荐厂家更多厂家(11)

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上海瀚思化工有限公司	18939883912 021-34536277	顾经理	3003949364	询单
上海绩祥生物科技有限公司	13093077543	陆经理	3985448220	询单
金锦乐（湖南）化学有限公司		金锦乐	1226360695	询单
JACS-郑州杰克斯化工产品有限公司	15981966935 0371-86259281	杰克斯JACS	893596907	询单
上海源叶生物科技有限公司	15026964105 15026964105	汤思磊	2881489226	询单
江苏艾康生物医药研发有限公司	18795912720 025-66061636	杨情情	3004779232	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单
DSL-CHEM				询单

(R)-1,1'-联萘-2,2'-二甲酸(80703-23-7)合成路线

合成路线：1 步

113567-21-8

_95%

80703-23-7

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran , Water ; overnight, rt → reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ; acidified

参考文献：

Process improvement on the preparation of chiral binaphthyl dicarboxylic acid

Yin, Li-hua; et al, Huaxue Shiji, 2012, 34(3), 277-279

合成路线：1 步

121314-72-5

_95%

80703-23-7

反应条件：

1.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol ; 18 h, 30 °C
1.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Synthesis of Axially Chiral Biaryls via Enantioselective Ullmann Coupling of ortho-Chlorinated Aryl Aldehydes Enabled by a Chiral 2,2'-Bipyridine Ligand

Perveen, Saima; et al, Angewandte Chemie, 2022, 61(47),

合成路线：1 步

121314-72-5

_68%

80703-23-7

反应条件：

1.1 Reagents: Monosodium phosphate , Hydrogen peroxide Solvents: Acetonitrile
1.2 Reagents: Sodium chlorite Solvents: Water
1.3 Reagents: Sodium sulfite Solvents: Water
1.4 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Facile synthesis of enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acid via lipase-catalyzed kinetic resolution

Furutani, Toshiyuki; et al, Tetrahedron: Asymmetry, 1999, 10(24), 4763-4768

合成路线：1 步

76373-22-3

_95%

80703-23-7

反应条件：

1.1 Reagents: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Acetone , Water ; reflux; 8 h, reflux

参考文献：

Synthesis of (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid

Yan, Luoyi, Anhui Huagong, 2012, 38(3), 26-28

合成路线：2 步

76373-22-3

80703-23-7

反应条件：

1.1 Reagents: Manganese oxide (MnO2) Solvents: Toluene
2.1 Reagents: Monosodium phosphate , Hydrogen peroxide Solvents: Acetonitrile
2.2 Reagents: Sodium chlorite Solvents: Water
2.3 Reagents: Sodium sulfite Solvents: Water
2.4 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Facile synthesis of enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acid via lipase-catalyzed kinetic resolution

Furutani, Toshiyuki; et al, Tetrahedron: Asymmetry, 1999, 10(24), 4763-4768

合成路线：1 步

122921-78-2

64-17-5

_94%

80703-23-7

反应条件：

1.1 Reagents: Dimethylformamide , Thionyl chloride Solvents: Thionyl chloride
1.2 Reagents: Potassium hydroxide Solvents: Ethanol , Water
1.3 Reagents: Sodium hydroxide Solvents: Water
1.4 Reagents: Hydrochloric acid Solvents: Water

参考文献：

A practical method for optical resolution of 1,1'-binaphthyl-2,2'-dicarboxylic acid via 1-phenylethylamides

Oi, Shuichi; et al, Bulletin of the Chemical Society of Japan, 1989, 62(3), 956-7

合成路线：1 步

86688-08-6

124-38-9

_90%

80703-23-7

反应条件：

1.1 Reagents: tert-Butyllithium Solvents: Tetrahydrofuran ; 30 min, -72 °C
1.2 17 - 24 h, -72 °C

参考文献：

Practical synthetic protocols of enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acid and 2,2'-dicyano-1,1'-binaphthyl starting from optically active dibromide precursor

Hoshi, Takashi; et al, Tetrahedron Letters, 2004, 45(17), 3485-3487

合成路线：1 步

2089435-04-9

_89%

80703-23-7

反应条件：

1.1 Reagents: Potassium hydroxide Solvents: Methanol , Water ; 21 h, reflux; reflux → rt
1.2 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Practical synthesis of axially chiral dicarboxylates via Pd-catalyzed external-CO-free carbonylation

Konishi, Hideyuki; et al, Chemical & Pharmaceutical Bulletin, 2016, 64(10), 1438-1441

合成路线：1 步

99827-46-0

_38%

80703-23-7

反应条件：

1.1 Reagents: Dimethylamine , (-)-1-Cyclohexylethylamine Solvents: Methanol , Water
1.2 Reagents: Hydrochloric acid Solvents: Water

参考文献：

A practical synthesis of C2-symmetric chiral binaphthyl ketone catalyst

Seki, Masahiko; et al, Synthesis, 2000, (12), 1677-1680

合成路线：1 步

99827-46-0

_23%

80703-23-7

反应条件：

1.1 Reagents: (-)-1-Cyclohexylethylamine Solvents: Methanol , Water ; 65 °C; 1.5 h, 65 °C → 25 °C

参考文献：

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Zhang, Huaiyuan; et al, Chemistry - A European Journal, 2022, 28(5),

合成路线：1 步

170117-58-5

80703-23-7

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Water

参考文献：

New method of kinetic resolution of axially chiral biaryl compounds using a sugar template.

Itoh, Toshiyuki; et al, Journal of Organic Chemistry, 1995, 60(16), 4968-9

合成路线：1 步

190734-00-0

80703-23-7

参考文献：

Product class 4: organometallic complexes of copper

Heaney, H.; et al, Science of Synthesis, 2004, 3, 305-662

合成路线：1 步

564476-06-8

80703-23-7

反应条件：

1.1 Reagents: Potassium hydroxide Solvents: Ethanol , Water ; 2 h, reflux

参考文献：

New asymmetric synthesis of several biaryl diacids and dinaphthol via biaryl coupling reaction induced by chiral auxiliaries

Qin, Chuan; et al, Youji Huaxue, 2002, 22(12), 1013-1017

合成路线：2 步

74866-28-7

124-38-9

80703-23-7

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ; -78 °C; 1 h, -78 °C
1.2 -78 °C → rt; 20 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ; acidified, rt
2.1 Reagents: (-)-1-Cyclohexylethylamine Solvents: Methanol , Water ; 65 °C; 1.5 h, 65 °C → 25 °C

参考文献：

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Zhang, Huaiyuan; et al, Chemistry - A European Journal, 2022, 28(5),

合成路线：2 步

126613-06-7

1864-94-4

80703-23-7

反应条件：

1.1 Reagents: Diisopropylethylamine Catalysts: Palladium diacetate , 1,3-Bis(diphenylphosphino)propane Solvents: Acetonitrile ; 24 h, 80 °C
2.1 Reagents: Potassium hydroxide Solvents: Methanol , Water ; 21 h, reflux; reflux → rt
2.2 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Practical synthesis of axially chiral dicarboxylates via Pd-catalyzed external-CO-free carbonylation

Konishi, Hideyuki; et al, Chemical & Pharmaceutical Bulletin, 2016, 64(10), 1438-1441

合成路线：2 步

反应条件：

1.1 Reagents: Diisopropylethylamine Catalysts: Palladium diacetate , 1,3-Bis(diphenylphosphino)propane Solvents: Methanol , Dimethyl sulfoxide ; 72 h, 80 °C
2.1 Reagents: Sodium hydroxide Solvents: Tetrahydrofuran , Water ; overnight, rt → reflux
2.2 Reagents: Hydrochloric acid Solvents: Water ; acidified

参考文献：

Process improvement on the preparation of chiral binaphthyl dicarboxylic acid

Yin, Li-hua; et al, Huaxue Shiji, 2012, 34(3), 277-279

合成路线：2 步

14304-75-7

80703-23-7

反应条件：

1.1 Reagents: Zinc Catalysts: Bis(triphenylphosphine)nickel dichloride , 2764676-49-3 Solvents: N-Methyl-2-pyrrolidone ; 16 h, 45 °C
2.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol ; 18 h, 30 °C
2.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Synthesis of Axially Chiral Biaryls via Enantioselective Ullmann Coupling of ortho-Chlorinated Aryl Aldehydes Enabled by a Chiral 2,2'-Bipyridine Ligand

Perveen, Saima; et al, Angewandte Chemie, 2022, 61(47),

合成路线：2 步

99827-46-0

2627-86-3

80703-23-7

反应条件：

1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Tetrahydrofuran
1.2 -
1.3 Solvents: Acetonitrile
1.4 Solvents: Ethanol
2.1 Reagents: Dimethylformamide , Thionyl chloride Solvents: Thionyl chloride
2.2 Reagents: Potassium hydroxide Solvents: Ethanol , Water
2.3 Reagents: Sodium hydroxide Solvents: Water
2.4 Reagents: Hydrochloric acid Solvents: Water

参考文献：

A practical method for optical resolution of 1,1'-binaphthyl-2,2'-dicarboxylic acid via 1-phenylethylamides

Oi, Shuichi; et al, Bulletin of the Chemical Society of Japan, 1989, 62(3), 956-7

合成路线：2 步

2862113-80-0

3378-82-3

80703-23-7

反应条件：

1.1 Reagents: Tetrabutylammonium iodide , Zinc Catalysts: Bis(triphenylphosphine)nickel dichloride , 2764676-49-3 Solvents: N-Methyl-2-pyrrolidone ; 16 h, 45 °C
2.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol ; 18 h, 30 °C
2.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Synthesis of Axially Chiral Biaryls via Enantioselective Ullmann Coupling of ortho-Chlorinated Aryl Aldehydes Enabled by a Chiral 2,2'-Bipyridine Ligand

Perveen, Saima; et al, Angewandte Chemie, 2022, 61(47),

合成路线：2 步

96260-22-9

3162-96-7

80703-23-7

反应条件：

1.1 -
2.1 Reagents: Sodium hydroxide Solvents: Water

参考文献：

New method of kinetic resolution of axially chiral biaryl compounds using a sugar template.

Itoh, Toshiyuki; et al, Journal of Organic Chemistry, 1995, 60(16), 4968-9

合成路线：2 步

3378-82-3

80703-23-7

反应条件：

参考文献：

Synthesis of Axially Chiral Biaryls via Enantioselective Ullmann Coupling of ortho-Chlorinated Aryl Aldehydes Enabled by a Chiral 2,2'-Bipyridine Ligand

Perveen, Saima; et al, Angewandte Chemie, 2022, 61(47),

合成路线：2 步

85464-88-6

80703-23-7

反应条件：

1.1 Reagents: Potassium hydroxide Solvents: Methanol , Water
1.2 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Dimethylamine , (-)-1-Cyclohexylethylamine Solvents: Methanol , Water
2.2 Reagents: Hydrochloric acid Solvents: Water

参考文献：

A practical synthesis of C2-symmetric chiral binaphthyl ketone catalyst

Seki, Masahiko; et al, Synthesis, 2000, (12), 1677-1680