环丙基亚磺酸酯 | 89729-09-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧硫杂环戊烷
• 中文名称: 环丙基亚磺酸酯
• 中文别名: 1,1-环丙烷二甲醇亚磺酸酯
• 英文名称: 5,7-dioxa-6-thia-spiro[2.5]octane 6-oxide
• 英文别名: 1,1-cyclopropanedimethanol cyclosulfite；5,7-Dioxa-6-thiaspiro[2.5]octane 6-oxide；5,7-dioxa-6λ4-thiaspiro[2.5]octane 6-oxide
• CAS: 89729-09-9
• 化学式: C₅H₈O₃S
• mdl: MFCD09832878
• 分子量: 148.183
• InChiKey: AISMUYPWEMPRTF-UHFFFAOYSA-N

物化性质

• 沸点：
  243℃
• 密度：
  1.51
• 闪点：
  101℃
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8℃，需密封并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1,1-Cyclopropane dimethanol cyclic sulfite
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: 1,1-Cyclopropane dimethanol cyclic sulfite
CAS number: 89729-09-9

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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: C5H8O3S
Molecular weight: 148.2

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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, sulfur 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：

  环丙基亚磺酸酯 在 四丁基氟化铵 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 (1-fluoromethyl-cyclopropyl)-acetaldehyde
  参考文献：
  名称：

  SPIROPYRROLIDINES AS MDM2 INHIBITORS

  摘要：

  描述了作为MDM2/p53相互作用抑制剂的螺环吡咯烷(I)，并提供了用于治疗癌症和视网膜黄斑变性等疾病的有用药剂。本发明的化合物具有一般性。进一步描述了包括本发明的一个或多个化合物、药学上可接受的盐或前药以及药学上可接受的载体或赋形剂的药物组合物。

  公开号：

  US20150322076A1
• 作为产物：
  描述：

  1,1-环丙烷二甲醇 在 吡啶 、 氯化亚砜 作用下， 反应 1.0h， 生成 环丙基亚磺酸酯
  参考文献：
  名称：

  1,3-乙二醇衍生物的化学。三、1,1-双(1-羟烷基)环丙烷的制备及其卤化

  摘要：

  通过1,1-二酰基环丙烷及其相关化合物的还原，制备了多种1,1-双(1-羟烷基)环丙烷。分离出一些立体异构体，并通过对二醇缩醛化制备的 1,3-二恶烷的 NMR 研究确定它们的构型。对二醇进行卤化。尽管内消旋和 dl-双 (1-羟乙基) 环丙烷与亚硫酰氯和五氯化磷的反应得到正常的二氯化物，伴有轻微的骨架重排，但立体特异性相当低。使用 ZnCl2-HCl，特异性完全丧失，并形成了大量的高烯丙基衍生物。讨论了反应机理。

  DOI：

  10.1246/bcsj.53.146

文献信息

• Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates
  作者：Meredith S. Eno、Alexander Lu、James P. Morken

  DOI：10.1021/jacs.6b03384

  日期：2016.6.29

  Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate

  描述了对称环状硫酸盐和芳香格氏试剂之间的镍催化的对映选择性交叉偶联。这些反应对广泛的取代环硫酸盐有效，并提供具有不对称叔碳中心的产物。机理实验表明，镍络合物在亲电子底物上发生了立体反转的 SN2 样氧化加成反应。
• Preparation of Cyclic Sulfites by Transesterification of Diols and Diisopropyl Sulfite
  作者：Steven A. King、Brenda Pipik、David A. Conlon、M. Bhupathy

  DOI：10.1080/00397919708003344

  日期：1997.2

  Abstract Cyclic Sulfites of 1,2-, 1,3- and 1,4-diols can be prepared in high yield by acid or base catalyzed transesterification with diisopropyl sulfite.

  摘要 1,2-、1,3-和1,4-二醇的环状亚硫酸盐可以通过酸或碱催化与亚硫酸二异丙酯的酯交换反应以高收率制备。
• Process for the preparation of a leukotriene antagonist and intermediates thereof
  申请人：ESTEVE QUIMICA, S.A.

  公开号：EP1783117A1

  公开（公告）日：2007-05-09

  It comprises a preparation process of Montelukast from an intermediate compound of formula (V), which is previously prepared by reaction of the corresponding sulfonate with 1-(mercaptomethyl)cyclopropyl)methanol. Compound (V) is reacted with a Grignard reactant to convert the ester group into a tertiary alcohol, followed by conversion of the primary alcohol into a sulfonate, substitution of the sulfonate group by a cyano group, and finally transforming the cyano compound to the carboxilic acid compound by a hydrolysis reaction to afford Montelukast. Montelukast can also be prepared by a hydrolysis reaction of the corresponding amide. It also comprises intermediate compounds useful in such preparation process.

  它包括从公式（V）的中间化合物制备蒙特卢卡斯特的制备过程，该中间化合物是通过相应磺酸盐与1-(巯基甲基)环丙基甲醇的反应预先制备的。化合物（V）与格氏试剂反应，将酯基转化为三级醇，然后将一次醇转化为磺酸盐，用氰基取代磺酸盐基团，最后通过水解反应将氰基化合物转化为羧酸化合物以制备蒙特卢卡斯特。蒙特卢卡斯特也可以通过相应酰胺的水解反应制备。还包括在这种制备过程中有用的中间化合物。
• 5-氮杂螺[2.4]庚烷-6-甲酸衍生物的合成方 法
  申请人：杭州科巢生物科技有限公司

  公开号：CN104788361B

  公开（公告）日：2017-06-30

  本发明提供一种(5S)‑5‑氮杂螺[2.4]庚烷‑6‑甲酸衍生物的合成方法，以1,1‑环丙二甲醇为起始原料，与二氯亚砜反应、经氧化得到磺酸酯化合物，然后与甘氨酸甲酯制备的亚胺在叔丁醇钾作用下缩合，再通过调节体系酸性、碱性一锅煮完成水解、环合、氨基保护得到消旋产品，最后经过拆分得到成品，总收率达到30%以上，该反应路线步骤短，用到的试剂安全，操作简单，反应成本低，收率较高，适宜工业化生产。
• Process for the Preparation of a Leukotriene Antagonist and Intermediates Thereof
  申请人：Coppi Laura

  公开号：US20080306270A1

  公开（公告）日：2008-12-11

  It comprises a preparation process of Montelukast from a new intermediate compound of formula (VI), which is previously prepared by reaction of the corresponding sulfonate with 1-(mercaptomethyl)cyclopropyl)methanol. Compound (VI) is reacted with a Grignard reactant to convert the ester group into a tertiary alcohol, followed by conversion of the primary alcohol into a sulfonate, substitution of the sulfonate group by a cyano group, and finally transforming the cyano compound to the carboxilic acid compound by a hydrolysis reaction to afford Montelukast. Montelukast can also be prepared by a hydrolysis reaction of the corresponding amide. It also comprises new intermediate compounds useful in such preparation process.

  本发明涉及一种从公式（VI）的新中间化合物制备蒙特卢卡斯特的制备过程，该中间化合物是通过将相应的磺酸盐与1-（巯基甲基）环丙基甲醇反应而预先制备的。化合物（VI）与格氏试剂反应，将酯基转化为三级醇，然后将一级醇转化为磺酸盐，用氰基取代磺酸基，最后通过水解反应将氰基化合物转化为羧酸化合物，从而得到蒙特卢卡斯特。蒙特卢卡斯特也可以通过相应酰胺的水解反应制备。本发明还包括在这种制备过程中有用的新中间化合物。