1-[2-(2-iodo-4,5-methylenedioxyphenyl)ethyl]octahydroindole-7a-carbonitrile | 809233-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-[2-(2-iodo-4,5-methylenedioxyphenyl)ethyl]octahydroindole-7a-carbonitrile
• 英文别名: 1-[2-(6-iodo-1,3-benzodioxol-5-yl)ethyl]-3,3a,4,5,6,7-hexahydro-2H-indole-7a-carbonitrile
• CAS: 809233-39-4
• 化学式: C₁₈H₂₁IN₂O₂
• 分子量: 424.281
• InChiKey: SRFZMIXDUGXSHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(2-iodo-4,5-methylenedioxyphenyl)ethyl]octahydroindole-7a-carbonitrile 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到cis-15,16-Methylendioxyerythrinan
  参考文献：
  名称：

  An Improved Stereocontrolled Route to cis-Erythrinanes by Combined Intramolecular Strecker and Bruylants Reaction

  摘要：

  Condensation of (2-iodophenyl)ethylamines with cyclohexanoylacetaldehyde provided the corresponding aldimines which were reduced yielding secondary phenethylcyclohexanoylethylamines. These in turn were appropriate intermediates to prepare several erythrinanes by a sequential intramolecular Strecker and intramolecular Bruylants reaction. In contrast, the C-ring homologue schelhammeranes were not available on this route.

  DOI：

  10.1007/s00706-004-0184-8
• 作为产物：
  描述：

  (1,4-dioxaspiro[4.5]dec-6-yl)acetic acid ethyl ester 在 盐酸 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 1-[2-(2-iodo-4,5-methylenedioxyphenyl)ethyl]octahydroindole-7a-carbonitrile
  参考文献：
  名称：

  An Improved Stereocontrolled Route to cis-Erythrinanes by Combined Intramolecular Strecker and Bruylants Reaction

  摘要：

  Condensation of (2-iodophenyl)ethylamines with cyclohexanoylacetaldehyde provided the corresponding aldimines which were reduced yielding secondary phenethylcyclohexanoylethylamines. These in turn were appropriate intermediates to prepare several erythrinanes by a sequential intramolecular Strecker and intramolecular Bruylants reaction. In contrast, the C-ring homologue schelhammeranes were not available on this route.

  DOI：

  10.1007/s00706-004-0184-8