2-(2-Oxo-5-vinyl-pyrrolidin-1-yl)-benzaldehyde | 229645-37-8

• 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: 2-(2-Oxo-5-vinyl-pyrrolidin-1-yl)-benzaldehyde
• 英文别名: 2-(2-Ethenyl-5-oxopyrrolidin-1-yl)benzaldehyde
• CAS: 229645-37-8
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: BJVZJLZDIVIXEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Oxo-5-vinyl-pyrrolidin-1-yl)-benzaldehyde 在 锂硼氢 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 12.0h， 生成 Methanesulfonic acid 3-[(3aS,4S,9bS)-1-benzyl-5-(2,2,2-trifluoro-acetyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-4-yl]-propyl ester
  参考文献：
  名称：

  Total Synthesis of (±)-Martinellic Acid

  摘要：

  [GRAPHICS]A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH4 and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degreesC as key steps,

  DOI：

  10.1021/ol016884o
• 作为产物：
  描述：

  1-(2-Hydroxymethyl-phenyl)-5-vinyl-pyrrolidin-2-one 在 manganese(IV) oxide 作用下， 反应 12.0h， 以96%的产率得到2-(2-Oxo-5-vinyl-pyrrolidin-1-yl)-benzaldehyde
  参考文献：
  名称：

  Total Synthesis of (±)-Martinellic Acid

  摘要：

  [GRAPHICS]A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH4 and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degreesC as key steps,

  DOI：

  10.1021/ol016884o

文献信息

• Synthesis of the tricyclic triamine core of martinelline and martinellic acid
  作者：Barry B. Snider、Yong Ahn、Bruce M. Foxman

  DOI：10.1016/s0040-4039(99)00461-x

  日期：1999.4

  The tricyclic triamine core 27 of martinellic acid (2) has been prepared stereospecifically in eight steps from 2-hydroxymethylaniline in 11% overall yield. The key steps are the addition of 2-hydroxymethylaniline to vinylcyclopropane 14 to prepare cycloaddition precursor 19 in only two steps and an intramolecular [3+2] azomethine ylide cycloaddition reaction to produce tetracycle 20 with >9:1 diastereoselectivity. (C) 1999 Elsevier Science Ltd, All rights reserved.
• Total Synthesis of (±)-Martinellic Acid
  作者：Barry B. Snider、Yong Ahn、Sean M. O'Hare

  DOI：10.1021/ol016884o

  日期：2001.12.1

  [GRAPHICS]A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH4 and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degreesC as key steps,