(6,6-ethylenedioxy-1E-hexenyl)tri-n-butylstannane | 1357181-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (6,6-ethylenedioxy-1E-hexenyl)tri-n-butylstannane
• CAS: 1357181-68-0
• 化学式: C₂₀H₄₀O₂Sn
• 分子量: 431.246
• InChiKey: VAMSWEJEAPVRRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6,6-ethylenedioxy-1E-hexenyl)tri-n-butylstannane 在 4-二甲氨基吡啶 、 氢气 、 三乙胺 、 红铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.92h， 生成 ((4bR,6S,8R,9aS,10aS)-6-(3-(1,3-dioxolan-2-yl)propyl)-4-isopropyl-4b,7,8,9,9a,10a-hexahydro-6H,11H-indeno[1',2':4,5]oxazolo[3,2-a]pyridin-8-yl)methyl 4-methylbenzenesulfonate
  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
• 作为产物：
  描述：

  5-己炔醛 在 偶氮二异丁腈 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 (6,6-ethylenedioxy-1E-hexenyl)tri-n-butylstannane
  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

• New type of azacyclization: thermal preparation of 4,6-disubstituted 2-piperidinone from N-sulfonyldienamide and its substituent effect
  作者：Yuya Maekawa、Taku Sakaguchi、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1016/j.tetlet.2011.12.014

  日期：2012.2

  The thermal 6-endo cyclization of N-sulfonyl-2,4-dienamide compounds to produce 4,6-disubstituted 2-piperidinone is described. The observed remarkable substituent effect due to the N-sulfonyl and C3 ethoxycarbonyl groups for acceleration of this 6-endo cyclization strongly suggests that the reaction would proceed via the 6 pi-azaelectrocyclization of the intermediary imidic acid. On the contrary, the corresponding 5-formyl and 5-acetyl derivatives rapidly cyclized at room temperature to produce the 5-exo cyclized products. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.