(S)-1-chloro-3-benzyloxy-2-propanol | 128572-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-chloro-3-benzyloxy-2-propanol
• 英文别名: (2S)-1-benzyloxy-3-chloro-propan-2-ol；(S)-1-benzyloxy-3-chloro-2-propanol；1-benzyloxy-3-chloro-2(S)-propanol；(2S)-1-chloro-3-phenylmethoxypropan-2-ol
• CAS: 128572-86-1
• 化学式: C₁₀H₁₃ClO₂
• 分子量: 200.665
• InChiKey: FJXVYZMGZACQOS-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-chloro-3-benzyloxy-2-propanol 在 水 、 sodium hydroxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 ((2R,5R)-5-((benzyloxy)methyl)-1,4-dioxan-2-yl)methanol
  参考文献：
  名称：

  WO2019241789A5

  摘要：

  公开号：

  WO2019241789A5
• 作为产物：
  描述：

  苄基缩水甘油醚 在 Candida antarctica lipase B 、 dilithium tetrachlorocuprate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 84.0h， 生成 (S)-1-chloro-3-benzyloxy-2-propanol
  参考文献：
  名称：

  Organic co-solvents restore the inherently high enantiomeric ratio of lipase B from Candida antarctica in hydrolytic resolution by relieving the enantiospecific inhibition of product alcohol

  摘要：

  The enantiomeric ratio in the hydrolysis of racemic 3-chloro-1-phenylmethoxy-2-propyl butanoate with lipase B from Candida antarctica, CALB, is raised from E=50 to E=180 upon addition of acetone to the aqueous medium. This co-solvent effect is now explained as an enantiospecific inhibition of the lipase by the liberated alcohol. In the range from 0 to 30% acetone, the effect correlates with the increased solubility of the alcohol in the reaction medium. Free and immobilized CALB show similar behaviour. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00273-0

文献信息

• Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: applications in the synthesis of reboxetine
  作者：Abdul Rouf Dar、Mushtaq A. Aga、Brijesh Kumar、Syed Khalid Yousuf、Subhash Chandra Taneja

  DOI：10.1039/c3ob40853a

  日期：——

  A regioselective high yielding monochloro substitution (chlorohydrin formation) via Mitsunobu reaction is reported. In carbohydrates and sterically hindered non-sugars, only the primary hydroxyl group is chlorinated, whereas in the non-sugar 1,2- and 1,3-alcohols, predominantly the secondary chloride substitution occurs. The versatile methodology provides indirect access to epoxides with the retention

  据报道通过Mitsunobu反应的区域选择性高产一氯取代（氯醇形成）。在碳水化合物和受阻位的非糖中，仅伯羟基被氯化，而在非糖1,2-和1,3-醇中，主要发生仲氯取代。与常规的Mitsunobu反应可逆生成环氧化物的方法不同，通用的方法可在保留结构的情况下间接获得环氧化物。该方法已成功用作抗抑郁药光学活性非对映异构体合成的关键步骤瑞波西汀（R）-2，3- O-环己叉基-D-甘油醛的总产率为〜43％。
• Chlorohydroxyacetone derivative and process for producing optically active chloropropanediol derivative from the same
  申请人：——

  公开号：US20020160398A1

  公开（公告）日：2002-10-31

  A process for efficiently preparing an optically active chloropropanediol derivative, especially (S)-1-benzyloxy-3-chloro-2-propanol, which has a high optical purity and is useful as an intermediate for medicines. The process comprises treating an inexpensive racemic chloropropanediol derivative with a nitroxyl compound and an oxidizing agent to convert it into a chlorohydroxyacetone derivative and then stereospecifically reducing the carbonyl group of the chlorohydroxyacetone derivative by the action of either a carbonyl-reducing enzyme having the ability to stereospecifically reduce the chlorohydroxyacetone derivative or an optically treated culture of a microorganism having the ability to yield the carbonyl-reducing enzyme. Thus, an optically active chloropropanediol derivative is prepared.

  一种高效制备光学活性氯代丙二醇衍生物的方法，特别是(S)-1-苄氧基-3-氯-2-丙醇，该衍生物具有高光学纯度并可用作药物中间体。该方法包括将廉价的外消旋氯代丙二醇衍生物与亚硝基化合物和氧化剂处理，将其转化为氯羟基丙酮衍生物，然后通过使用具有立体选择性还原氯羟基丙酮衍生物能力的羰基还原酶或具有产生羰基还原酶的光学处理微生物培养物的作用，立体选择性地还原氯羟基丙酮衍生物的羰基基团。因此，制备了光学活性氯代丙二醇衍生物。
• Combination of gold and redox enzyme catalysis to access valuable enantioenriched aliphatic β-chlorohydrins
  作者：Lorena Escot、Sergio González-Granda、Vicente Gotor-Fernández、Iván Lavandera

  DOI：10.1039/d2ob01953a

  日期：——

  The synthesis of enantioenriched β-chlorohydrins is highly appealing due to their relevance as building-blocks in organic synthesis. However, the approximation to aliphatic derivatives is particularly challenging due to the difficulties to get access to the α-chloroketone precursors. Herein, we propose a straightforward and scalable approach combining in a concurrent manner gold(I) and redox enzyme

  富含对映体的 β-氯醇的合成因其作为有机合成中的构建单元的相关性而极具吸引力。然而，由于难以获得 α-氯酮前体，因此接近脂肪族衍生物特别具有挑战性。在此，我们提出了一种直接且可扩展的方法，通过水合-生物还原级联以并发方式结合金 ( I ) 和氧化还原酶催化。总共获得了九种带有不同官能团的脂肪族 β-氯代醇，具有非常高的产率 (63–88%) 和立体选择性 (>99% ee)。
• CHLOROHYDROXYACETONE DERIVATIVE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE CHLOROPROPANEDIOL DERIVATIVE FROM THE SAME
  申请人：KANEKA CORPORATION

  公开号：EP1298119A1

  公开（公告）日：2003-04-02

  A process for efficiently preparing an optically active chloropropanediol derivative, especially (S)-1-benzyloxy-3-chloro-2-propanol, which has a high optical purity and is useful as an intermediate for medicines. The process comprises treating an inexpensive racemic chloropropanediol derivative with a nitroxyl compound and an oxidizing agent to convert it into a chlorohydroxyacetone derivative and then stereospecifically reducing the carbonyl group of the chlorohydroxyacetone derivative by the action of either a carbonyl-reducing enzyme having the ability to stereospecifically reduce the chlorohydroxyacetone derivative or an optically treated culture of a microorganism having the ability to yield the carbonyl-reducing enzyme. Thus, an optically active chloropropanediol derivative is prepared.

  一种有效制备光学活性氯丙二醇衍生物，特别是(S)-1-苄氧基-3-氯-2-丙醇的工艺，其光学纯度高，可用作药物中间体。该工艺包括用硝基化合物和氧化剂处理廉价的外消旋氯丙二醇衍生物，将其转化为氯羟基丙酮衍生物，然后在具有立体还原氯羟基丙酮衍生物能力的羰基还原酶或具有产生羰基还原酶能力的微生物的光学处理培养物的作用下，立体还原氯羟基丙酮衍生物的羰基。这样，一种具有光学活性的氯丙二醇衍生物就制备出来了。
• Rapamycin analogs and uses thereof
  申请人：Navitor Pharmaceuticals, Inc.

  公开号：US10980784B2

  公开（公告）日：2021-04-20

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用方法。