Ethyl (1R,2S)-1-amino-2-ethenylcyclopropanecarboxylate sulphate (2:1) | 1173807-85-6

• 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
• 英文名称: Ethyl (1R,2S)-1-amino-2-ethenylcyclopropanecarboxylate sulphate (2:1)
• 英文别名: [(1R,2S)-2-ethenyl-1-ethoxycarbonylcyclopropyl]azanium;sulfate
• CAS: 1173807-85-6
• 化学式: C16H28N2O8S
• 分子量: 408.5
• InChiKey: KCWPGHMPJQDAAN-BLHVZGRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  188
• 氢给体数：
  4
• 氢受体数：
  10

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (1R,2S)-Ethyl 1-amino-2-vinylcyclopropanecarboxylate hemisulfate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: (1R,2S)-Ethyl 1-amino-2-vinylcyclopropanecarboxylate hemisulfate
CAS number: 1173807-85-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H13NO2
Molecular weight: 155.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  、 Ethyl (1R,2S)-1-amino-2-ethenylcyclopropanecarboxylate sulphate (2:1) 、 sodium hydroxide 、 对氯苯甲酸 在 solvent 、 甲苯 作用下， 以 水 为溶剂， 反应 49.5h， 以to obtain (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester 4-chlorobenzoate (17.7 g, 56.7 mmol)的产率得到(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester 4-chlorobenzoate
  参考文献：
  名称：

  METHOD FOR PRODUCING OPTICALLY ACTIVE 1-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ESTER

  摘要：

  1-氨基-2-乙烯基环丙烷羧酸酯是一种有用的药物合成中间体，可以通过以下步骤制备：包括水解一个由式（3）表示的手性1-N-(芳基亚甲基)氨基-2-乙烯基环丙烷羧酸酯，该酯是通过在碱和手性季铵盐存在下将式（1）表示的N-(芳基亚甲基)甘氨酸酯与式（2）表示的化合物反应而获得的。

  公开号：

  US20120130116A1
• 作为产物：
  描述：

  (1r,2s)-1-氨基-2-乙烯-环丙烷羧酸乙酯 、 硫酸 在 甲苯 、 氮气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.83h， 以to result in a liquid amount of 3.2 L的产率得到Ethyl (1R,2S)-1-amino-2-ethenylcyclopropanecarboxylate sulphate (2:1)
  参考文献：
  名称：

  METHOD FOR PRODUCING 1-AMINO-1-ALKOXYCARBONYL-2-VINYLCYCLOPROPANE

  摘要：

  本发明的目的是提供一种新的方法，用于生产用作丙型肝炎治疗剂的合成中间体和其合成中间体的(1R,2S)/(1S,2R)-1-氨基-1-烷氧羰基-2-乙烯基环丙烷。根据本发明，在存在碱的情况下，将具有1-位和4-位上各自的离去基的反式-2-丁烯衍生物与丙二酸酯反应，使用特定量的碱金属烷氧化物或碱金属氢化物作为碱，进一步使用特定量的丙二酸酯产生环丙烷二酯，进一步使用手性或非手性1-氨基-1-烷氧羰基-2-乙烯基环丙烷及其盐合物合成，使用环丙烷二酯。

  公开号：

  US20130096339A1

文献信息

• METHOD FOR PRODUCING OPTICALLY ACTIVE 1-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ESTER
  申请人：Aikawa Toshiaki

  公开号：US20120130116A1

  公开（公告）日：2012-05-24

  1-Amino-2-vinylcyclopropanecarboxylic acid ester, which is useful as a synthetic intermediate of pharmaceuticals, can be produced by a process of producing 1-amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (4): including a step of hydrolysis of an optically active 1-N-(arylmethylene)amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (3): which is obtained by reacting an N-(arylmethylene)glycine ester represented by formula (1): with a compound represented by formula (2): in the presence of a base and an optically active quaternary ammonium salt.

  1-氨基-2-乙烯基环丙烷羧酸酯是一种有用的药物合成中间体，可以通过以下步骤制备：包括水解一个由式（3）表示的手性1-N-(芳基亚甲基)氨基-2-乙烯基环丙烷羧酸酯，该酯是通过在碱和手性季铵盐存在下将式（1）表示的N-(芳基亚甲基)甘氨酸酯与式（2）表示的化合物反应而获得的。
• METHOD FOR PRODUCING 1-AMINO-1-ALKOXYCARBONYL-2-VINYLCYCLOPROPANE
  申请人：Asuma Yuuki

  公开号：US20130096339A1

  公开（公告）日：2013-04-18

  It is an object of the present invention to provide a novel method for producing (1R,2S)/(1S,2R)-1-amino-1-alkoxycarbonyl-2-vinylcyclopropane which is useful as a synthetic intermediate of therapeutic agents for hepatitis C and a synthetic intermediate thereof. According to the present invention, when a trans-2-butene derivative having a leaving group at each of the 1- and 4-positions is reacted with a malonic ester in the presence of a base, a specific amount of an alkali metal alkoxide or an alkali metal hydride is used as the base, and further a specific amount of a malonic ester is used to produce a cyclopropane diester, and further, chiral or achiral 1-amino-1-alkoxy-carbonyl-2-vinylcyclopropane and a salt thereof are synthesized using the cyclopropane diester.

  本发明的目的是提供一种新的方法，用于生产用作丙型肝炎治疗剂的合成中间体和其合成中间体的(1R,2S)/(1S,2R)-1-氨基-1-烷氧羰基-2-乙烯基环丙烷。根据本发明，在存在碱的情况下，将具有1-位和4-位上各自的离去基的反式-2-丁烯衍生物与丙二酸酯反应，使用特定量的碱金属烷氧化物或碱金属氢化物作为碱，进一步使用特定量的丙二酸酯产生环丙烷二酯，进一步使用手性或非手性1-氨基-1-烷氧羰基-2-乙烯基环丙烷及其盐合物合成，使用环丙烷二酯。
• Method for producing 1-amino-1-alkoxycarbonyl-2-vinylcyclopropane
  申请人：Asuma Yuuki

  公开号：US09061991B2

  公开（公告）日：2015-06-23

  It is an object of the present invention to provide a novel method for producing (1R,2S)/(1S,2R)-1-amino-1-alkoxycarbonyl-2-vinylcyclopropane which is useful as a synthetic intermediate of therapeutic agents for hepatitis C and a synthetic intermediate thereof. According to the present invention, when a trans-2-butene derivative having a leaving group at each of the 1- and 4-positions is reacted with a malonic ester in the presence of a base, a specific amount of an alkali metal alkoxide or an alkali metal hydride is used as the base, and further a specific amount of a malonic ester is used to produce a cyclopropane diester, and further, chiral or achiral 1-amino-1-alkoxy-carbonyl-2-vinylcyclopropane and a salt thereof are synthesized using the cyclopropane diester.

  本发明的目的是提供一种新的方法，用于制备作为丙型肝炎治疗剂和其合成中间体的(1R,2S)/(1S,2R)-1-氨基-1-烷氧羰基-2-乙烯基环丙烷。根据本发明，在存在碱的情况下，将具有1-和4-位置上的离去基的反式2-丁烯衍生物与丙二酸酯反应，使用特定量的碱金属醇或碱金属氢化物作为碱，进一步使用特定量的丙二酸酯产生环丙烷二酯，然后使用环丙烷二酯合成手性或非手性的1-氨基-1-烷氧羰基-2-乙烯基环丙烷及其盐。
• Method for producing optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester
  申请人：Aikawa Toshiaki

  公开号：US08742162B2

  公开（公告）日：2014-06-03

  1-Amino-2-vinylcyclopropanecarboxylic acid ester, which is useful as a synthetic intermediate of pharmaceuticals, can be produced by a process of producing 1-amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (4): including a step of hydrolysis of an optically active 1-N-(arylmethylene)amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (3): which is obtained by reacting an N-(arylmethylene)glycine ester represented by formula (1): with a compound represented by formula (2): in the presence of a base and an optically active quaternary ammonium salt.

  1-氨基-2-乙烯基环丙烷羧酸酯是药物的合成中间体，可以通过以下步骤生产代表式为（4）的1-氨基-2-乙烯基环丙烷羧酸酯：首先在碱和手性季铵盐的存在下，通过将代表式为（1）的N-(芳基亚甲基)甘氨酸酯与代表式为（2）的化合物反应，得到代表式为（3）的手性1-N-(芳基亚甲基)氨基-2-乙烯基环丙烷羧酸酯，然后进行水解。