(2R,3S)-1-amino-pent-4-ene-2,3-diol hydrochloride | 1241411-26-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,3S)-1-amino-pent-4-ene-2,3-diol hydrochloride
• 英文别名: (2R,3S)-1-aminopent-4-ene-2,3-diol;hydrochloride
• CAS: 1241411-26-6
• 化学式: C₅H₁₁NO₂*ClH
• 分子量: 153.609
• InChiKey: JNXPXBTUQFVRCU-UYXJWNHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.5
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-amino-pent-4-ene-2,3-diol hydrochloride 在 碘 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 18.0h， 以99%的产率得到(6R,7S,7aR)-6,7-二羟基四氢-1H-吡咯并[1,2-c][1,3]恶唑-3-酮
  参考文献：
  名称：

  A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines

  摘要：

  A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.016
• 作为产物：
  描述：

  (2R,3S)-1-aminopent-4-ene-2,3-diol 在 盐酸 作用下， 以 水 为溶剂， 以25 mg的产率得到(2R,3S)-1-amino-pent-4-ene-2,3-diol hydrochloride
  参考文献：
  名称：

  A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines

  摘要：

  A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.016

文献信息

• A novel and environmental friendly synthetic route for hydroxypyrrolidines using zeolites
  作者：A. Fan、G.K. Chuah、Stephan Jaenicke

  DOI：10.1016/j.carres.2018.11.016

  日期：2019.1

  150, where a yield of >83% was obtained. The overall yields of the five-step procedure to 1,4-dideoxy-1,4-imino-l-lyxitol and 1,4-dideoxy-1,4-imino-d-lyxitol were 57% and 50%, respectively. This synthetic procedure has several advantages such as competitive overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the zeolite catalyst can be easily recovered from the reaction

  由相应的d糖合成羟基吡咯烷，1,4-dideoxy-1,4-imino-l-lyxitol和1,4-dideoxy-1,4-imino-d-lyxitol的关键步骤是合成O-甲基2，3-O-异亚丙基戊烯呋喃糖酶。人们发现，采用沸石的多相催化可直接用于由d-糖直接合成O-甲基2,3-O-异亚丙基戊二酸呋喃糖酶，而不是采用传统的无机酸催化剂（如HCl和HClO4）进行均相催化过程，甲醇和丙酮在温和的条件下。最好的催化剂是Si / Al摩尔比为150的H-β沸石，其收率> 83％。对于1，4-二脱氧-1，4-亚氨基-1-糖醇的五步法的总产率分别为57％和50％。该合成方法具有许多优点，例如具有竞争力的总产率，减少的步骤数和温和的反应条件。此外，可以容易地从反应混合物中回收沸石催化剂，并在不损失活性的情况下对其进行再利用。
• A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines
  作者：Emma M. Dangerfield、Shivali A. Gulab、Catherine H. Plunkett、Mattie S.M. Timmer、Bridget L. Stocker

  DOI：10.1016/j.carres.2010.03.016

  日期：2010.7

  A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of alpha-picoline borane as a more environmentally benign reducing agent, is also presented. (C) 2010 Elsevier Ltd. All rights reserved.