racemic N-hydroxymethyl vince lactam

• 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: racemic N-hydroxymethyl vince lactam
• 英文别名: (1S,4R)-2-(hydroxymethyl)-2-azabicyclo[2.2.1]hept-5-en-3-one
• 化学式: C₇H₉NO₂
• 分子量: 139.154
• InChiKey: YIVZLGMTDFTBEO-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  racemic N-hydroxymethyl vince lactam 在 盐酸 、 水 作用下， 反应 5.0h， 生成 (1R,4S)-4-氨基-2-环戊烯-1-羧酸盐酸盐(1:1)
  参考文献：
  名称：

  Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction

  摘要：

  A very efficient enzymatic two-step cascade reaction was devised (E > 200) for the resolution of activated gamma-lactams (+/-)-1 and (+/-)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5 equiv) in the presence of benzylamine (1 equiv) in i-Pr2O at 60 degrees C. The ring-opened enantiomerically pure gamma-amino acids (1S,4R)-6 (ee = 99%, intermediate of abacavir) and (1S,3R)-8 (ee = 99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee >= 96%) were obtained in good yields (>= 43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6 center dot HCl and (1S,3R)-8 center dot HCI or (15,4R)-3 and (1R,4S)-4 quantitatively, with ee >= 96%. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.019
• 作为产物：
  描述：

  2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 potassium carbonate 作用下， 反应 6.0h， 生成 racemic N-hydroxymethyl vince lactam
  参考文献：
  名称：

  Lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones

  摘要：

  The lipase-catalyzed asymmetric resolution of 2-azabicyclo[2.2.1] hept-5-en-3-ones is reported; non-racemic chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification or hydrolysis of N-hydroxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one or N-acyloxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one.

  DOI：

  10.1016/0957-4166(96)00293-5

文献信息

• A facile lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones
  作者：Hiroto Nakano、Yuko Okuyama、Kazuto Iwasa、Hiroshi Hongo

  DOI：10.1016/0957-4166(94)80144-4

  日期：1994.7

  The lipase-catalyzed asymmetric synthesis of optically active 2-azabicyclo[2.2.1]hept-5-en-3-ones is reported. Chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification of 2-hydroxymethyl-2-azabicyclo-[2.2.1]hept-5-en-3-one.
• Highly efficient resolution of N-hydroxymethyl vince lactam by solvent stable lipase YCJ01
  作者：Ling Zhu、Fucheng Zhu、Song Qin、Bin Wu、Bingfang He

  DOI：10.1016/j.molcatb.2016.12.009

  日期：2016.11
• Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction
  作者：Zsolt Galla、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2016.06.019

  日期：2016.9

  A very efficient enzymatic two-step cascade reaction was devised (E > 200) for the resolution of activated gamma-lactams (+/-)-1 and (+/-)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5 equiv) in the presence of benzylamine (1 equiv) in i-Pr2O at 60 degrees C. The ring-opened enantiomerically pure gamma-amino acids (1S,4R)-6 (ee = 99%, intermediate of abacavir) and (1S,3R)-8 (ee = 99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee >= 96%) were obtained in good yields (>= 43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6 center dot HCl and (1S,3R)-8 center dot HCI or (15,4R)-3 and (1R,4S)-4 quantitatively, with ee >= 96%. (C) 2016 Elsevier Ltd. All rights reserved.
• Lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones
  作者：Hiroto Nakano、Kazuto Iwasa、Yuko Okuyama、Hiroshi Hongo

  DOI：10.1016/0957-4166(96)00293-5

  日期：1996.8

  The lipase-catalyzed asymmetric resolution of 2-azabicyclo[2.2.1] hept-5-en-3-ones is reported; non-racemic chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification or hydrolysis of N-hydroxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one or N-acyloxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one.