(1R,2S)-1-[(2S,4R,6R)-2-[3-(1,3-dioxolan-2-yl)propyl]-6-ethenyl-4-methylpiperidin-1-yl]-7-propan-2-yl-2,3-dihydro-1H-inden-2-ol | 1436412-00-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (1R,2S)-1-[(2S,4R,6R)-2-[3-(1,3-dioxolan-2-yl)propyl]-6-ethenyl-4-methylpiperidin-1-yl]-7-propan-2-yl-2,3-dihydro-1H-inden-2-ol
• CAS: 1436412-00-8
• 化学式: C₂₆H₃₉NO₃
• 分子量: 413.601
• InChiKey: DVKQUPPVPLIAAA-KJGOFRKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-pentyneyl)-1,3-dioxolane 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 氢气 、 三乙胺 、 红铝 、 sodium iodide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.09h， 生成 (1R,2S)-1-((2S,4R,6S)-2-(3-(1,3-dioxolan-2-yl)propyl)-4-methyl-6-vinylpiperidin-1-yl)-7-isopropyl-2,3-dihydro-1H-inden-2-ol 、 (1R,2S)-1-[(2S,4R,6R)-2-[3-(1,3-dioxolan-2-yl)propyl]-6-ethenyl-4-methylpiperidin-1-yl]-7-propan-2-yl-2,3-dihydro-1H-inden-2-ol
  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

• 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.