顺-1,2-环丙烷二羧酸二甲酯 | 826-34-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 顺-1,2-环丙烷二羧酸二甲酯
• 中文别名: 顺-1,2-环丙二甲酸二甲酯
• 英文名称: dimethyl cis-cyclopropane-1,2-dicarboxylate
• 英文别名: dimethyl (1R,2S)-cyclopropane-1,2-dicarboxylate；Dimethyl cis-1,2-cyclopropanedicarboxylate；dimethyl (1S,2R)-cyclopropane-1,2-dicarboxylate
• CAS: 826-34-6
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: JBVOSZYUSFDYIN-SYDPRGILSA-N

物化性质

• 沸点：
  112 °C (18 mmHg)
• 密度：
  1.15
• 保留指数：
  1101
• 稳定性/保质期：
  在常温常压下稳定，避免与不相容材料接触。应避免与强氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R22
• 海关编码：
  2917209090

SDS

Name:	Dimethyl Cis-1 2-Cyclopropanedicarboxylate 98% Material Safety Data Sheet
Synonym:	None
CAS:	826-34-6

Section 1 - Chemical Product MSDS Name:Dimethyl Cis-1 2-Cyclopropanedicarboxylate 98% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
826-34-6	Dimethyl Cis-1,2-Cyclopropanedicarboxy	98	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
Containers can build up pressure if exposed to heat and/or fire. As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 826-34-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 112 deg C @ 18.00mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.1580g/cm3
Molecular Formula: C7H10O4
Molecular Weight: 158.16

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 826-34-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Dimethyl Cis-1,2-Cyclopropanedicarboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 826-34-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 826-34-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 826-34-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  顺-1,2-环丙烷二羧酸二甲酯 在 盐酸 、 氢氧化钾 作用下， 生成 cis-1,2-cyclopropanedicarboxylic acid
  参考文献：
  名称：

  Saal, Wolfgang von der; Reinhardt, Robert; Seidenspinner, Hubert-Matthias, Liebigs Annalen der Chemie, 1989, p. 703 - 712

  摘要：

  DOI：
• 作为产物：
  描述：

  环丙烷-1,2-二羧酸二乙酯 以 甲醇 、 乙醚 为溶剂， 生成 顺-1,2-环丙烷二羧酸二甲酯
  参考文献：
  名称：

  猪肝酯酶立体对称水解二酯的研究

  摘要：

  猪肝esterase-（PLE）的对称的二羧酸，其中包括二甲基酯的催化水解内消旋-diacids，顺式-1,2-环烷烃酸，并用前手性中心二酸，用14个基板研究。这些立体选择性水解的产物是二元羧酸的手性单酯，对映体过量（ee）为10％至100％。这些光学活性单酯中的一些是天然产物合成中有价值的合成子。

  DOI：

  10.1002/hlca.19830660815

文献信息

• Chemokine receptor binding heterocyclic compounds with enhanced efficacy
  申请人：——

  公开号：US20030220341A1

  公开（公告）日：2003-11-27

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  这项发明涉及由一个核心氮原子环绕着三个侧链基团的杂环化合物，其中三个侧链基团中的两个最好是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可选地含有额外的环。这些化合物与趋化因子受体结合，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护作用。
• Reductive cleavage of succinic esters. A method for the introduction of acetic acid fragments
  作者：Paul G. Gassman、Xavier Creary

  DOI：10.1039/c39720001214

  日期：——

  Diels–Alder addition of maleic or fumaric esters to 1,3-dienes, followed by catalytic reduction and treatment with sodium in liquid ammonia at –78°, which promotes a solvent dependent reductive cleavage of the carbon–carbon σ bond of the succinic ester fragment, provides a general method for the preparation of derivatives of suberic acid.

  Diels–将马来酸酯或富马酸酯加到1,3-二烯中，然后催化还原并在–78°下用液态氨中的钠进行处理，从而促进了琥珀酸酯的碳-碳σ键的溶剂依赖性还原裂解片段提供了一种制备辛二酸衍生物的通用方法。
• [EN] PHENYL-(AZA)CYCLOALKYL CARBOXYLIC ACID GPR120 MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS GPR120 À BASE D'ACIDE PHÉNYL-(AZA)CYCLOALKYLCARBOXYLIQUE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016040225A1

  公开（公告）日：2016-03-17

  The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are GPR120 G protein-coupled receptor modulators which may be used as medicaments.

  本发明提供了化合物的结构式(I)：或其立体异构体，或其药学上可接受的盐，其中所有变量如本文所定义。这些化合物是GPR120 G蛋白偶联受体调节剂，可用作药物。
• SUBSTITUTED PIPERAZINO-DIHYDROTHIENOPYRIMIDINES
  申请人：Pouzet Pascale

  公开号：US20110021501A1

  公开（公告）日：2011-01-27

  The invention relates to new piperidino-dihydrothienopyrimidines of formula 1, as well as pharmacologically acceptable salts thereof, wherein X is SO or SO 2 , but preferably SO, and wherein R 1 , R 2 , R 3 and R 4 may have the meanings given in claim 1 , as well as pharmaceutical compositions which contain these compounds. These new piperidino-dihydrothienopyrimidines are suitable for the treatment of respiratory or gastrointestinal complaints or diseases, inflammatory diseases of the joints, skin or eyes, diseases of the peripheral or central nervous system or cancers.

  本发明涉及通式1的新哌啶二氢噻吩并嘧啶类化合物及其药理上可接受的盐，其中X为SO或SO2，优选SO，并且其中R1、R2、R3和R4可具有权利要求1中所述的含义，以及含有这些化合物的药物组合物。这些新哌啶二氢噻吩并嘧啶类化合物适用于治疗呼吸系统或胃肠道疾病、关节、皮肤或眼睛的炎症性疾病、周围或中枢神经系统疾病或癌症。
• Substituent Effect in the Ionization of<i>cis</i>-2-Substituted 1-Cyclopropanecarboxylic Acids
  作者：Yoshiaki Kusuyama

  DOI：10.1246/bcsj.52.1944

  日期：1979.7

  Ten cis-2-substituted 1-cyclopropanecarboxylic acids (substituents: H, CH3, C6H5, CH3O, C2H5O, Cl, Br, CH3CO, CH3OCO, and C2H5OCO) were prepared, and their pKa values were determined in water at 25 °C, along with those of the trans-2-chloro and 2-methoxy derivatives. The pKa values for cis isomers are somewhat larger than those for the corresponding trans isomers, except for the chloro and bromo derivatives. The substituent effects obtained were in the usual order in the sense of the electronic effects, except for the phenyl group, which produced a decrease in acidity relative to the unsubstituted acid. It was shown that the carbon-13 chemical shifts for the methylene carbon of the ethyl group in the ethyl cis-2-substituted 1-cyclopropanecarboxylate obtained in deuteriochloroform gave a reasonable linear relation with the pKa(cis) values.

  合成了十种顺式-2-取代的1-环丙烷羧酸（取代基：H、CH3、C6H5、CH3O、C2H5O、Cl、Br、CH3CO、CH3OCO和C2H5OCO），并在25°C的水中测定了它们的pKa值，以及对应的反式-2-氯和2-甲氧基衍生物的pKa值。顺式异构体的pKa值普遍高于相应的反式异构体，氯和溴衍生物除外。得到的取代基效应与电子效应的通常顺序一致，除了苯基，苯基相对未取代酸表现出酸性下降。研究表明，在去氘氯仿中获得的乙基顺式-2-取代1-环丙烷羧酸酯的亚甲基碳的碳-13化学位移与pKa(cis)值之间存在合理的线性关系。

表征谱图