(3aR,4R,9aS,9bS)-4-(iodomethyl)-2,2-dimethyl-3a,4,6,9,9a,9b-hexahydro-[1,3]dioxolo[4,5-a]indolizine | 641609-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,9aS,9bS)-4-(iodomethyl)-2,2-dimethyl-3a,4,6,9,9a,9b-hexahydro-[1,3]dioxolo[4,5-a]indolizine
• CAS: 641609-82-7
• 化学式: C₁₂H₁₈INO₂
• 分子量: 335.185
• InChiKey: CQEGIJDQJWQMEI-XWLWVQCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,4R,9aS,9bS)-4-(iodomethyl)-2,2-dimethyl-3a,4,6,9,9a,9b-hexahydro-[1,3]dioxolo[4,5-a]indolizine 在 sodium azide 、 silver perchlorate 作用下， 以 四氢呋喃 、 氘代氯仿 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1S,2R,3R,9aS)-3-azido-1,2-O-isopropylidene-7,8-didehydroquinolizidine-1,2-diol
  参考文献：
  名称：

  A Short Route toward Chiral, Polyhydroxylated Indolizidines and Quinolizidines

  摘要：

  In this paper, a rapid route toward functionalized bicyclic alkaloids is presented. In only three steps, an easily accessible carbohydrate derivative was converted into iodomethyl indolizidine 13, which can equilibrate to the corresponding iodoquinolizidine 15. We provide strong evidence that this equilibration proceeds via an aziridinium ion intermediate. Furthermore, nucleophilic substitution of the iodomethyl indolizidine as well as the aziridinium intermediate gives access to highly functionalized indolizidine and quinolizidine alkaloids.

  DOI：

  10.1021/jo0350662
• 作为产物：
  描述：

  (3R,4S,5S)-3,4-O-isopropylidene-5-(N-allylamino)octa-1,7-diene-3,4-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) camphor-10-sulfonic acid 、 碘 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (3aR,4R,9aS,9bS)-4-(iodomethyl)-2,2-dimethyl-3a,4,6,9,9a,9b-hexahydro-[1,3]dioxolo[4,5-a]indolizine
  参考文献：
  名称：

  A Short Route toward Chiral, Polyhydroxylated Indolizidines and Quinolizidines

  摘要：

  In this paper, a rapid route toward functionalized bicyclic alkaloids is presented. In only three steps, an easily accessible carbohydrate derivative was converted into iodomethyl indolizidine 13, which can equilibrate to the corresponding iodoquinolizidine 15. We provide strong evidence that this equilibration proceeds via an aziridinium ion intermediate. Furthermore, nucleophilic substitution of the iodomethyl indolizidine as well as the aziridinium intermediate gives access to highly functionalized indolizidine and quinolizidine alkaloids.

  DOI：

  10.1021/jo0350662

文献信息

• A Short Route toward Chiral, Polyhydroxylated Indolizidines and Quinolizidines
  作者：Steven H. L. Verhelst、Baltasar Paez Martinez、Mattie S. M. Timmer、Gerrit Lodder、Gijsbert A. van der Marel、Herman S. Overkleeft、Jacques H. van Boom

  DOI：10.1021/jo0350662

  日期：2003.12.1

  In this paper, a rapid route toward functionalized bicyclic alkaloids is presented. In only three steps, an easily accessible carbohydrate derivative was converted into iodomethyl indolizidine 13, which can equilibrate to the corresponding iodoquinolizidine 15. We provide strong evidence that this equilibration proceeds via an aziridinium ion intermediate. Furthermore, nucleophilic substitution of the iodomethyl indolizidine as well as the aziridinium intermediate gives access to highly functionalized indolizidine and quinolizidine alkaloids.