7-[(1S)-1-羟基丙基]-8-甲基-吲哚嗪并[1,2-b]喹啉-9(11H)-酮 | 54318-59-1

• 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
• 中文名称: 7-[(1S)-1-羟基丙基]-8-甲基-吲哚嗪并[1,2-b]喹啉-9(11H)-酮
• 英文名称: (S)-(-)-mappicine
• 英文别名: (S)-mappicine；mappicine；7-[(1S)-1-hydroxypropyl]-8-methyl-11H-indolizino[1,2-b]quinolin-9-one
• CAS: 54318-59-1
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: WSXJPXFVULHYMX-KRWDZBQOSA-N

物化性质

• 沸点：
  616.0±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-[(1S)-1-羟基丙基]-8-甲基-吲哚嗪并[1,2-b]喹啉-9(11H)-酮 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到麦皮星酮
  参考文献：
  名称：

  异腈的自由基级联反应合成（S）-哌甲啶和甲吡甲酮

  摘要：

  （S）-Mappicine（2）和Mappicine酮（1）由乙酰乙酸甲酯（4）通过以异腈自由基级联反应为关键步骤的策略制备。通过不对称羟基化以适度的选择性引入（S）-甲哌啶的羟基。

  DOI：

  10.1016/s0040-4020(97)90398-7
• 作为产物：
  描述：

  (S)-mappicine acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到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

文献信息

• The first conversion of camptothecin to ( S )-mappicine by an efficient chemoenzymatic method
  作者：Biswanath Das、P Madhusudhan、A Kashinatham

  DOI：10.1016/s0960-894x(98)00234-0

  日期：1998.6

  Camptothecin has been converted for the first time to (S)-mappicine via mappicine ketone, which is the sole product of the microwave irradiation of camptothecin. Baker's yeast reduction of mappicine ketone yielded (S)-mappicine in high optical purity.

  喜树碱已首次通过马卡比汀酮转化为（S）-马比汀，这是喜树碱微波辐射的唯一产物。贝克酵母对马比汀甲酮的还原产生了高光学纯度的（S）-马比汀。
• Quasiracemic Synthesis:  Concepts and Implementation with a Fluorous Tagging Strategy to Make Both Enantiomers of Pyridovericin and Mappicine
  作者：Qisheng Zhang、Alexey Rivkin、Dennis P. Curran

  DOI：10.1021/ja025606x

  日期：2002.5.1

  The concept of quasiracemic synthesis is introduced and illustrated with syntheses of both enantiomers of pyridovericin (whose absolute configuration is assigned as R) and mappicine. Like racemic synthesis, quasiracemic synthesis provides both enantiomers in a single synthetic sequence; however, separation tagging is used to ensure that quasiracemic mixtures can be analyzed, separated, and identified

  介绍了准外消旋合成的概念，并通过吡啶多菌素（其绝对构型指定为 R）和麦匹辛的两种对映异构体的合成进行了说明。与外消旋合成一样，准外消旋合成在单一合成序列中提供两种对映异构体；然而，分离标记用于确保准外消旋混合物可以按需分析、分离和识别。不同链长的氟标签用于标记两种对映体起始材料。将所得准对映体混合以制备准外消旋物，然后在合成的连续步骤中将其像真正的外消旋物一样处理。氟色谱法用于将最终的准外消旋物分离或分层为两种组分，然后将其分离以提供（真正的）对映体产品。
• 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.
• 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.
• Total Synthesis of Nothapodytine B and (−)-Mappicine
  作者：Dale L. Boger、Jiyong Hong

  DOI：10.1021/ja973007y

  日期：1998.2.1

  Concise total syntheses of naturally occurring nothapodytine B (1, mappicine ketone) and (-)-mappicine (3) are detailed. The approach is based on the implementation of a room-temperature, inverse electron demand Diels-Alder react ion of the N-sulfonyl-1-aza-1,3-butadiene 11 for assemblage of a pyridone D ring precursor central to the structure. A Friedlander condensation is utilized for constructing the AB ring system of 1 and 3. An acid-catalyzed reaction sequence is used to accomplish a deprotection with subsequent ring-closure for introduction of the C ring in a single step.