(S,S)-trans-2,5-bis(hydroxymethyl)pyrrolidine | 157604-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S,S)-trans-2,5-bis(hydroxymethyl)pyrrolidine
• 英文别名: (2S,5S)-2,5-dihydroxymethylpyrrolidine；[(2S,5S)-5-(hydroxymethyl)pyrrolidin-2-yl]methanol
• CAS: 157604-83-6
• 化学式: C₆H₁₃NO₂
• 分子量: 131.175
• InChiKey: ITNFYTQOVXXQNN-WDSKDSINSA-N

物化性质

• 沸点：
  260.1±15.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,S)-trans-2,5-bis(hydroxymethyl)pyrrolidine 在 盐酸 、 三乙胺 、 mercury dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,5S)-2,5-Bis-hydroxymethyl-pyrrolidine-1-carboxamidine; hydrochloride
  参考文献：
  名称：

  Enantiopure Guanidine Bases For Enantioselective Enone Epoxidations: 1, Acyclic Guanidines

  摘要：

  一系列结构和功能各异的手性纯化氨基脲已被制备并应用于对3-叔丁氧基羧酰氨基-4,4-二甲氧基环己烯-2,5-二烯-1-酮1的手性选择性环氧化，反应中使用了叔丁基过氧化氢。观察到成功的手性选择性环氧化，并获得了有用的结构-活性数据，但反应速度较慢，观察到的最大对映体过量为30%。

  DOI：

  10.1055/s-2003-37105
• 作为产物：
  描述：

  trans-2,5-dimethyl N-benzylpyrrolidine-2,5-dicarboxylate 在 palladium dihydroxide lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (S,S)-trans-2,5-bis(hydroxymethyl)pyrrolidine
  参考文献：
  名称：

  C 2对称反式-2,5-双（羟甲基）吡咯烷的两种对映体的合成。脂肪酶介导的顺序动力学拆分

  摘要：

  脂肪酶介导的顺序动力学拆分已被用于以光学纯的形式给出反式-2,5-双（羟甲基）吡咯烷的两种对映异构体。还报告了这些分辨率中不同参数对ee和产量的影响。

  DOI：

  10.1016/s0040-4039(00)73281-3
• 作为试剂：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 在 sodium acetate 、 乙酸酐 、 (S,S)-trans-2,5-bis(hydroxymethyl)pyrrolidine 作用下， 以 乙醚 为溶剂， 反应 52.0h， 生成
  参考文献：
  名称：

  Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines

  摘要：

  Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C-2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00473-9

文献信息

• [EN] OXAZEPINE COMPOUNDS AND USES THEREOF IN THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS D'OXAZÉPINE ET LEURS UTILISATIONS DANS LE TRAITEMENT DU CANCER
  申请人：GENENTECH INC

  公开号：WO2022216762A1

  公开（公告）日：2022-10-13

  Provided herein are acyclic oxazepinyl compounds useful in the treatment on cancers.

  本文提供了一些用于治疗癌症的非环状噁唑啉化合物。
• A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts
  作者：Aleksey I. Gerasyuto、Richard P. Hsung、Nadiya Sydorenko、Brian Slafer

  DOI：10.1021/jo050171s

  日期：2005.5.1

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.
• Versatile Synthesis of Enantiomerically Pure trans-2,5-Disubstituted Pyrrolidines
  作者：N. André Sasaki、Michael Dockner、Pierre Potier

  DOI：10.3987/com-95-s89

  日期：——
• [EN] AZA-TETRACYCLIC OXAZEPINE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS D'OXAZÉPINE AZA-TÉTRACYCLIQUES ET LEURS UTILISATIONS
  申请人：[en]GENENTECH, INC.

  公开号：WO2023225302A1

  公开（公告）日：2023-11-23

  Provided herein are aza-tetracyclic oxazepinyl compounds useful in the treatment of cancers.
• Enantiopure Guanidine Bases For Enantioselective Enone Epoxidations: 1, Acyclic Guanidines
  作者：Richard J. Taylor、Julie C. McManus、John S. Carey

  DOI：10.1055/s-2003-37105

  日期：——

  A range of structurally and functionally varied enantiopure guanidines has been prepared and evaluated in the enantioselective epoxidation of 3-tert-butoxycarbonylamino-4,4-dimethoxycyclohexa-2,5-dien-1-one 1 using tert-butylhydroperoxide. Successful enantioselective epoxidations were observed and useful structure-activity data obtained, but the reactions were slow and the maximum ee observed was 30%.

  一系列结构和功能各异的手性纯化氨基脲已被制备并应用于对3-叔丁氧基羧酰氨基-4,4-二甲氧基环己烯-2,5-二烯-1-酮1的手性选择性环氧化，反应中使用了叔丁基过氧化氢。观察到成功的手性选择性环氧化，并获得了有用的结构-活性数据，但反应速度较慢，观察到的最大对映体过量为30%。