(R,R)-trans-2,5-bis(hydroxymethyl)pyrrolidine | 126642-20-4

• 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: (R,R)-trans-2,5-bis(hydroxymethyl)pyrrolidine
• 英文别名: 2,5-Bis(hydroxymethyl)pyrrolidine；Rel-((2R,5R)-pyrrolidine-2,5-diyl)dimethanol；[(2R,5R)-5-(hydroxymethyl)pyrrolidin-2-yl]methanol
• CAS: 126642-20-4
• 化学式: C₆H₁₃NO₂
• mdl: MFCD19218571
• 分子量: 131.175
• InChiKey: ITNFYTQOVXXQNN-PHDIDXHHSA-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：

  (R,R)-trans-2,5-bis(hydroxymethyl)pyrrolidine 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 7.0h， 生成 trans-(hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-6-yl)methanol
  参考文献：
  名称：

  [EN] AZA-TETRACYCLIC OXAZEPINE COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS D'OXAZÉPINE AZA-TÉTRACYCLIQUES ET LEURS UTILISATIONS

  摘要：

  Provided herein are aza-tetracyclic oxazepinyl compounds useful in the treatment of cancers.

  公开号：

  WO2023225302A1
• 作为产物：
  描述：

  (+)-(2R,5R)-N-benzyl-2,5-bis(acetoxymethyl)pyrrolidine 在 palladium dihydroxide 氢气 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 (R,R)-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

文献信息

• Asymmetric cycloaddition of anthrone and maleimides catalyzed by C2-chiral pyrrolidines
  作者：Kouhei Uemae、Satoshi Masuda、Yukio Yamamoto

  DOI：10.1039/b100961n

  日期：——

  Catalytic asymmetric cycloaddition of anthrone with N-alkyl- and N-arylmaleimides with various substituents in the aromatic ring was carried out in the presence of C2-chiral pyrrolidines to afford chiral, non-racemic [4 + 2] adducts. Among them, good catalytic activity was observed with the pyrrolidines with a N-(4-pyridyl)methyl group 1h, which was discussed from the viewpoint of conformational analysis. The best stereoselectivity of 87% ee was attained when the reaction of N-(2-tert-butylphenyl)maleimide 4j and anthrone was promoted with 1h.

  在 C2 手性吡咯烷存在下，蒽酮与芳香环上具有不同取代基的 N-烷基和 N-芳基马来酰亚胺进行了催化不对称环加成反应，得到了手性非外消旋 [4 + 2] 加合物。其中，带有 N-（4-吡啶基）甲基的吡咯烷类化合物 1h 具有良好的催化活性，并从构象分析的角度对其进行了讨论。用 1h 促进 N-(2-叔丁基苯基)马来酰亚胺 4j 和蒽酮的反应，可获得 87%ee 的最佳立体选择性。
• Asymmetric induction in the conjugate addition of thioacetic acid to methacrylamides with chiral auxiliaries
  作者：Byung Hyun Kim、Hee Bong Lee、Jae Kwang Hwang、Young Gyu Kim

  DOI：10.1016/j.tetasy.2005.01.037

  日期：2005.3

  The conjugate addition of thioacetic acid to methacrylamides with chiral C-2-syrnmetric trans-2,5-disubstituted pyrrolidines afforded the addition products in excellent stereoselectivities (>99% de) and good yields (80-90%). The high selectivity was attributed mainly to the steric effect of the chiral auxiliaries. The cyclic nature of the chiral auxiliaries seemed also important for both the stereoselectivity and the reaction rate. Acidic hydrolysis of the adduct containing (2R,5R)-bis(methoxymethyl)pyrrotidine gave (S)-3-mercapto-2-methylpropanoic acid, a key intermediate for captopril, in 98% ee and 96% yield. The chiral auxiliary was recovered in the demethylated form of N-Boc-(2R,3R)-bis(hydroxymethyl)pyrrolidine in 90% yield. (C) 2005 Elsevier Ltd. All rights reserved.
• Sibi Mukund P., Lu JianLiang, Tetrahedron Lett, 35 (1994) N 28, S 4915-4918
  作者：Sibi Mukund P., Lu JianLiang

  DOI：——

  日期：——
• Synthesis of both enantiomers of C2 symmetric trans-2,5-bis(hydroxymethyl)pyrrolidine. Lipase mediated sequential kinetic resolutions
  作者：Mukund P. Sibi、JianLiang Lu

  DOI：10.1016/s0040-4039(00)73281-3

  日期：1994.7

  Lipase mediated sequential kinetic resolution has been employed to give both enantiomers of trans-2,5-bis(hydroxymethyl)pyrrolidine in optically pure form. The effect of different parameters on the ee and yields in these resolutions are also reported.

  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。
• [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.