(S)-9-methoxymappicine acetate | 243846-92-6

• 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: (S)-9-methoxymappicine acetate
• 英文别名: 9-methoxymappicine acetate；[(1S)-1-(1-methoxy-8-methyl-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl)propyl] acetate
• CAS: 243846-92-6
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: YXNVQOINAORMRM-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-9-methoxymappicine acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到(S)-9-methoxymappicine
  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：

  9-methoxymappicine 在 phosphate buffer 、 lipase Amano PS (Pseudomonas cepacia) 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 72.0h， 生成 (S)-9-methoxymappicine acetate
  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

• Acetylation of Camptothecins Using Lithium Bromide as Catalyst
  作者：N. Ravindranath、C. Ramesh、M. Ravinder Reddy、K. V. N. S. Srinivas、Biswanath Das

  DOI：10.1081/scc-120026340

  日期：2003.12.1

  Camptothecin and 9-Methoxycamptothecin, two promising naturally occurring anticancer alkaloids containing a tertiary hydroxy group, were acetylated with acetic anhydride at room temperature in the presence of lithium bromide as catalyst. The similar method was followed for acetylation of other two related natural alkaloids, mappicine and 9-methoxymappicine.
• Das; Madhusudhan, Journal of Chemical Research - Part S, 2000, # 10, p. 476 - 477
  作者：Das、Madhusudhan

  DOI：——

  日期：——