7-(1-acetoxy-propyl)-8-methyl-11H-indolizino[1,2-b]quinolin-9-one | 55822-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(1-acetoxy-propyl)-8-methyl-11H-indolizino[1,2-b]quinolin-9-one
• 英文别名: (+/-)-Mappicinacetat；1-(8-methyl-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl)propyl acetate
• CAS: 55822-01-0
• 化学式: C₂₁H₂₀N₂O₃
• 分子量: 348.401
• InChiKey: IXJCSPATZKEPFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(1-acetoxy-propyl)-8-methyl-11H-indolizino[1,2-b]quinolin-9-one 在 phosphate buffer 、 lipase Amano PS (Pseudomonas cepacia) 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 74.0h， 生成 7-[(1S)-1-羟基丙基]-8-甲基-吲哚嗪并[1,2-b]喹啉-9(11H)-酮
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-mappicines and their analogues

  摘要：

  The naturally occurring alkaloids, camptothecin and mappicine ketone were converted to racemic mappicine acetate which was enantioselectively hydrolyzed to (S)- and (R)-mappicines in high optical purity using baker's yeast and a lipase, Amano PS. Treatment of the racemic acetate with baker's yeast afforded (S)-mappicine while with Amano PS yielded (R)-mappicine. 9-Methoxycamptothecin and 9-methoxymappicine ketone underwent similar conversion to (S)- and (R)-9-methxymappicines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00397-x
• 作为产物：
  描述：

  麦皮星酮 在 sodium tetrahydroborate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 2.0h， 生成 7-(1-acetoxy-propyl)-8-methyl-11H-indolizino[1,2-b]quinolin-9-one
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-mappicines and their analogues

  摘要：

  The naturally occurring alkaloids, camptothecin and mappicine ketone were converted to racemic mappicine acetate which was enantioselectively hydrolyzed to (S)- and (R)-mappicines in high optical purity using baker's yeast and a lipase, Amano PS. Treatment of the racemic acetate with baker's yeast afforded (S)-mappicine while with Amano PS yielded (R)-mappicine. 9-Methoxycamptothecin and 9-methoxymappicine ketone underwent similar conversion to (S)- and (R)-9-methxymappicines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00397-x

文献信息

• Enantioselective synthesis of (S)- and (R)-mappicines and their analogues
  作者：Biswanath Das、P. Madhusudhan

  DOI：10.1016/s0040-4020(99)00397-x

  日期：1999.6

  The naturally occurring alkaloids, camptothecin and mappicine ketone were converted to racemic mappicine acetate which was enantioselectively hydrolyzed to (S)- and (R)-mappicines in high optical purity using baker's yeast and a lipase, Amano PS. Treatment of the racemic acetate with baker's yeast afforded (S)-mappicine while with Amano PS yielded (R)-mappicine. 9-Methoxycamptothecin and 9-methoxymappicine ketone underwent similar conversion to (S)- and (R)-9-methxymappicines. (C) 1999 Elsevier Science Ltd. All rights reserved.