(S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((2R)-3-chloro-2-hydroxypropoxy)phenyl)propanoate | 1398109-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((2R)-3-chloro-2-hydroxypropoxy)phenyl)propanoate
• 英文别名: [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]propanoate
• CAS: 1398109-46-0
• 化学式: C₁₈H₂₅ClO₆
• 分子量: 372.846
• InChiKey: FSAZJCZUNWHHPR-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((2R)-3-chloro-2-hydroxypropoxy)phenyl)propanoate 在 盐酸 、 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 [(4S)-2,2-二甲基-1,3-二氧戊环-4-基]甲基 3-[4-[(2S)-2-羟基-3-[2-(吗啉-4-甲酰氨基)乙基氨基]丙氧基]苯基]丙酸酯盐酸盐
  参考文献：
  名称：

  란디올롤의 거울상선택적 합성 방법

  摘要：

  The method for producing randiolol 1, namely ((S)-2,2-dimethyl-1,3-dioxolane-4-yl)methyl 3-(4-((S)-2-hydroxy-3-(2-(morpholin-4-carboxamido)ethylamino)propoxy)phenyl)propanoate, as an alkylating agent with an epoxide structure, starting from 2-(morpholin-4-carboxamido)ethanamine, especially epichlorohydrin, and 2-(morpholin-4-carboxamido)ethanamine in the form of a glass base or its salt form. The method is carried out without separating most of the intermediates, does not require a purification process using chromatography, and has advantages in terms of yield and productivity. Additionally, the resulting randiolol can be easily converted into randiolol hydrochloride, which is particularly pure and has a high enantiomeric purity.

  公开号：

  KR101862824B1
• 作为产物：
  描述：

  (S)-(2,2-二甲基-1,3-二氧环戊烷-4-基)甲基 3-(4-羟基苯基)丙酸酯 、 环氧氯丙烷 在 (R,R)-(-)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane diaminocobalt(II) 、 对硝基苯甲酸 作用下， 以 二氯甲烷 、 甲基叔丁基醚 为溶剂， 以99.6%的产率得到(S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((2R)-3-chloro-2-hydroxypropoxy)phenyl)propanoate
  参考文献：
  名称：

  란디올롤의 거울상선택적 합성 방법

  摘要：

  The method for producing randiolol 1, namely ((S)-2,2-dimethyl-1,3-dioxolane-4-yl)methyl 3-(4-((S)-2-hydroxy-3-(2-(morpholin-4-carboxamido)ethylamino)propoxy)phenyl)propanoate, as an alkylating agent with an epoxide structure, starting from 2-(morpholin-4-carboxamido)ethanamine, especially epichlorohydrin, and 2-(morpholin-4-carboxamido)ethanamine in the form of a glass base or its salt form. The method is carried out without separating most of the intermediates, does not require a purification process using chromatography, and has advantages in terms of yield and productivity. Additionally, the resulting randiolol can be easily converted into randiolol hydrochloride, which is particularly pure and has a high enantiomeric purity.

  公开号：

  KR101862824B1

文献信息

• "Process for the enantioselective synthesis of landiolol"
  申请人：Procos S.p.A.

  公开号：EP2687521B1

  公开（公告）日：2015-01-07
• 란디올롤의 거울상선택적 합성 방법
  申请人：PROCOS S.p.A. 뿌로꼬스 엣세.삐.아.(520100370869)

  公开号：KR101862824B1

  公开（公告）日：2018-05-30

  (S)-(2,2-디메틸-1,3-디옥솔란-4-일)메틸 3-(4-히드록시페닐)프로파노에이트, 에폭시드 구조를 가진 알킬화제로서, 특히 에피클로로히드린, 그리고 유리 염기 또는 그의 염의 형태로 된 2-(모르폴린-4-카르복사미도)에탄아민으로부터 출발하여, 란디올롤 1, 즉 ((S)-2,2-디메틸-1,3-디옥솔란-4-일)메틸 3-(4-((S)-2-히드록시-3-(2-(모르폴린-4-카르복사미도)에틸아미노)프로폭시)페닐)프로파노에이트)를 제조하는 방법. 상기 방법은 대부분의 중간체를 분리하지 않고 이루어지며, 크로마토그래피를 이용한 정제과정을 요하지 않고, 특히 수율과 생산성 측면에서 이점을 가지고 있다. 게다가, 결과로 얻어진 란디올롤은 특히 순수하고, 높은 거울상체 순도를 가진 란디올롤 히드로클로리드로 용이하게 전환될 수 있다.

  The method for producing randiolol 1, namely ((S)-2,2-dimethyl-1,3-dioxolane-4-yl)methyl 3-(4-((S)-2-hydroxy-3-(2-(morpholin-4-carboxamido)ethylamino)propoxy)phenyl)propanoate, as an alkylating agent with an epoxide structure, starting from 2-(morpholin-4-carboxamido)ethanamine, especially epichlorohydrin, and 2-(morpholin-4-carboxamido)ethanamine in the form of a glass base or its salt form. The method is carried out without separating most of the intermediates, does not require a purification process using chromatography, and has advantages in terms of yield and productivity. Additionally, the resulting randiolol can be easily converted into randiolol hydrochloride, which is particularly pure and has a high enantiomeric purity.