(1aS,2aS,6S,6aR,7aR)-6-ethyl-5-oxo-2,2a,3,6a,7,7a-hexahydro-1aH-oxireno[2,3-g]isochromene-6-carbonitrile | 1356956-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1aS,2aS,6S,6aR,7aR)-6-ethyl-5-oxo-2,2a,3,6a,7,7a-hexahydro-1aH-oxireno[2,3-g]isochromene-6-carbonitrile
• CAS: 1356956-04-1
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: VHIACDGLWCGMAH-WSOSLHDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1aS,2aS,6S,6aR,7aR)-6-ethyl-5-oxo-2,2a,3,6a,7,7a-hexahydro-1aH-oxireno[2,3-g]isochromene-6-carbonitrile 在 Rh/Al₂O₃ 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 氘代四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 20.0~50.0 ℃ 、827.39 kPa 条件下， 反应 50.5h， 生成 (4S,4aR,6S,7S,8aS)-9-benzoyl-4-ethyl-7-hydroxyoctahydro-3H-6,4-(epiminomethano)isochromen-3-one
  参考文献：
  名称：

  Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A

  摘要：

  The planning and implementation of an enantioselective total synthesis of (+)-scholarisine A is presented. Key tactics employed include a novel cyclization, consisting of a nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer indolization; an oxidative lactonization of a diol in the presence of an indole ring; and a late-stage cyclization to complete the caged ring scaffold. The development of a possible "retro-biosynthetic" approach to other members of the akuammiline alkaloid family is also described.

  DOI：

  10.1021/ja3111626
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 lithium aluminium tetrahydride 、 正丁基锂 、 porcine pancreatic lipase Sigma type 2 、 potassium carbonate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 乙腈 为溶剂， 反应 245.17h， 生成 (1aR,2aS,6S,6aR,7aS)-6-ethyl-5-oxo-2,2a,3,6a,7,7a-hexahydro-1aH-oxireno[2,3-g]isochromene-6-carbonitrile 、 (1aS,2aS,6S,6aR,7aR)-6-ethyl-5-oxo-2,2a,3,6a,7,7a-hexahydro-1aH-oxireno[2,3-g]isochromene-6-carbonitrile
  参考文献：
  名称：

  Total Synthesis of (+)-Scholarisine A

  摘要：

  An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A.

  DOI：

  10.1021/ja211840k

文献信息

• Total Synthesis of (+)-Scholarisine A
  作者：Gregory L. Adams、Patrick J. Carroll、Amos B. Smith

  DOI：10.1021/ja211840k

  日期：2012.3.7

  An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A.
• Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A
  作者：Gregory L. Adams、Patrick J. Carroll、Amos B. Smith

  DOI：10.1021/ja3111626

  日期：2013.1.9

  The planning and implementation of an enantioselective total synthesis of (+)-scholarisine A is presented. Key tactics employed include a novel cyclization, consisting of a nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer indolization; an oxidative lactonization of a diol in the presence of an indole ring; and a late-stage cyclization to complete the caged ring scaffold. The development of a possible "retro-biosynthetic" approach to other members of the akuammiline alkaloid family is also described.