hippodamine | 53990-36-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 9b-氮杂菲类
• 英文名称: hippodamine
• CAS: 53990-36-6
• 化学式: C₁₃H₂₃N
• 分子量: 193.332
• InChiKey: MOQNYBQLQBMEKL-RNJOBUHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-benzyloxycarbonyl-6S-(4,4-ethylenedioxybutyl)-4R-methyl-2R-vinyl-piperidine 在 10 wt% Pd(OH)2 on carbon 、 三氟化硼乙醚 、 氢气 、 对甲苯磺酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 28.0h， 生成 hippodamine
  参考文献：
  名称：

  Total Synthesis of (−)-Hippodamine by Stereocontrolled Construction of Azaphenalene Skeleton Based on Extended One-Pot Asymmetric Azaelectrocyclization

  摘要：

  The first asymmetric total synthesis of (-)-hippodamine has been accomplished via the concise construction of its azaphenalene core, which Is featured by the 2,4,6-chiral piperidine synthesis based on one-pot asymmetric azaelectrocyclization in the partially activated substituent system and the subsequent intramolecular Mannich reaction.

  DOI：

  10.1021/ol4010917

文献信息

• Asymmetric Intramolecular Aza-Michael Reaction in Desymmetrization Processes. Total Synthesis of Hippodamine and <i>epi</i>-Hippodamine
  作者：Marta Guerola、María Sánchez-Roselló、Cristina Mulet、Carlos del Pozo、Santos Fustero

  DOI：10.1021/acs.orglett.5b00054

  日期：2015.2.20

  The use of chiral sulfinyl amines both as nucleophilic nitrogen sources and chiral inducers has been described for the first time in a desymmetrization-type process involving an intramolecular aza-Michael reaction. The resulting product was employed as an advanced intermediate in the total synthesis of the natural product hippodamine and epi-hippodamine, taking advantage of the special symmetry of

  在涉及分子内的氮杂-迈克尔反应的脱对称型方法中，首次描述了手性亚硫胺作为亲核氮源和手性诱导剂的使用。利用这些分子的特殊对称性，将所得产物用作天然产物河多巴胺和表-hippodamine的总合成中的高级中间体。此外，这是所述第一不对称全合成外延-hippodamine。
• Total Synthesis of (−)-Hippodamine by Stereocontrolled Construction of Azaphenalene Skeleton Based on Extended One-Pot Asymmetric Azaelectrocyclization
  作者：Shintaro Fujita、Taku Sakaguchi、Toyoharu Kobayashi、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1021/ol4010917

  日期：2013.6.7

  The first asymmetric total synthesis of (-)-hippodamine has been accomplished via the concise construction of its azaphenalene core, which Is featured by the 2,4,6-chiral piperidine synthesis based on one-pot asymmetric azaelectrocyclization in the partially activated substituent system and the subsequent intramolecular Mannich reaction.