(2S,1′R)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine | 123411-87-0

• 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: (2S,1′R)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine
• 英文别名: (2S,1'R)-N-benzyloxycarbonyl-2-(1'-hydroxybut-3'-en-1'-yl)pyrrolidine；benzyl (2S)-2-[(1R)-1-hydroxybut-3-enyl]pyrrolidine-1-carboxylate
• CAS: 123411-87-0
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: LIUHBIYSKBNWMA-LSDHHAIUSA-N

物化性质

• 沸点：
  419.4±28.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,1′R)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 336000.0h， 以20%的产率得到(1R,7S)-tetrahydro-1-(2-propenyl)-1H,3H-pyrrolo[1,2-c]oxazol-3-one
  参考文献：
  名称：

  A new strategy for the synthesis of hydroxylated pyrrolizidinic alkaloids by highly stereoselective indium-mediated allylation of pyrrolidinic aldehydes

  摘要：

  Indium-mediated allylation of N-Cbz-L-prolinal 3, under Grignard conditions, was carried out with high yield and stereoselectivity (de = 90%) to afford intermediate (2S, 1'R)-N-benzyloxycarbonyl-2-(1'-hydroxybut-3'-en-1'-yl)pyrrolidine 4, which was transformed in two steps into (1R,3R,7aS)-1-hydroxy-3-hydroxymethylpyrrolizidine 9. Commercial Cbz-L-proline was a source of functionalization and chirality. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.010
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 、 3-溴丙烯 在 indium 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以78%的产率得到(2S,1′R)-2-(1′-hydroxybut-3′-en-1′-yl)-1-(carbobenzyloxy)pyrrolidine
  参考文献：
  名称：

  A new strategy for the synthesis of hydroxylated pyrrolizidinic alkaloids by highly stereoselective indium-mediated allylation of pyrrolidinic aldehydes

  摘要：

  Indium-mediated allylation of N-Cbz-L-prolinal 3, under Grignard conditions, was carried out with high yield and stereoselectivity (de = 90%) to afford intermediate (2S, 1'R)-N-benzyloxycarbonyl-2-(1'-hydroxybut-3'-en-1'-yl)pyrrolidine 4, which was transformed in two steps into (1R,3R,7aS)-1-hydroxy-3-hydroxymethylpyrrolizidine 9. Commercial Cbz-L-proline was a source of functionalization and chirality. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.010

文献信息

• Facile, Stereocontrolled Synthetic Route towards Bis-functionalised Pyrrolizidines
  作者：Janusz Jurczak、Marcin Lindner、Antoni Krasiński

  DOI：10.1055/s-0037-1609582

  日期：2018.11

  Ligands, and Targets Abstract A simple and convenient method for the synthesis of bis-functionalised pyrrolizidines starting from readily available N-Cbz-l-prolinal is described. This aldehyde was converted within two concise steps to the corresponding aminoepoxides, which were separately subjected to regioselective cyclisation induced by a reductive cleavage of the Cbz protecting group. The versatile

  作为特殊主题杂环的一部分作为催化剂，配体和靶标发布 抽象的 描述了一种从容易获得的N -Cbz- 1-脯氨酸开始合成双官能化吡咯烷核苷的简单方便的方法。在两个简洁的步骤中，将该醛转化为相应的氨基环氧化物，将其分别进行还原选择性裂解Cbz保护基团诱导的区域选择性环化。通用而简洁的策略在直接制备基于吡咯利嗪的药物和天然产品中具有巨大的实际应用潜力。 描述了一种从容易获得的N -Cbz- 1-脯氨酸开始合成双官能化吡咯烷核苷的简单方便的方法。在两个简洁的步骤中，将该醛转化为相应的氨基环氧化物，将其分别进行还原选择性裂解Cbz保护基团诱导的区域选择性环化。通用而简洁的策略在直接制备基于吡咯利嗪的药物和天然产品中具有巨大的实际应用潜力。
• Dramatic changes in diastereoselectivity with the quantity of titanium tetrachloride used in Lewis acid mediated reactions of allylsilane with .alpha.-amino aldehydes
  作者：Syunichi Kiyooka、Masahito Nakano、Fuminori Shiota、Ryoji Fujiyama

  DOI：10.1021/jo00284a002

  日期：1989.11
• The titanium-catalysed epoxidation of homoallylic α-amino alcohols
  作者：Antoni Krasiński、Janusz Jurczak

  DOI：10.1016/s0957-4166(02)00511-6

  日期：2002.10

  Diastereoselective titanium-catalysed epoxidation reactions of acyclic homoallylic alcohols are presented. The results are compared to the stereochemical outcome obtained by the application of the commonly used vanadium catalyst, VO(acac)(2). The key role of the syn-bis-homoallylic carbamate group in obtaining high yields and reversed diastereoselectivities in the titanium-catalysed reactions is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.