cis-Erythrinan | 27711-98-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 刺桐生物碱
• 英文名称: cis-Erythrinan
• 英文别名: (4aS,13bS)-2,3,4,4a,5,6,8,9-octahydro-1H-indolo[7a,1-a]isoquinoline
• CAS: 27711-98-4
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: PERYEAFHHZTAKL-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-Erythrinan 在 lithium 、 乙胺 作用下， 生成 rac-14,15,16,17-tetrahydro-erythrinane
  参考文献：
  名称：

  Syntheses of 14,15,16,17-Tetrahydroerythrinane^1,2

  摘要：

  DOI：

  10.1021/ja01524a035
• 作为产物：
  描述：

  [2-(1,4-dioxaspiro[4.5]dec-6-yl)ethyl]-[2-(2-iodophenyl)ethyl]amine 在 盐酸 、 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 cis-Erythrinan
  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

文献信息

• SYNTHESIS IN THE FIELD OF THE ERYTHRINA ALKALOIDS: PART II. APPROACHES TO THE RING SYSTEM OF β-ERYTHROIDINE
  作者：B. Belleau

  DOI：10.1139/v57-095

  日期：1957.7.1

  The newly developed method for the elaboration of the ring system of the aromatic class of Erylhrina alkaloids has been successfully extended to the synthesis of 1,2,3,4-tetrahydroerythrinane (VI), a non-aromatic analogue. The key step in this synthesis involves ring closure of ketoamide (IV) itself, obtained from hexahydroindole and cyclohexenylacetic acid. Attempts to further extend this sequence

  新开发的用于合成 Eryhrina 生物碱芳香类环系的方法已成功扩展到 1,2,3,4-四氢赤藓烷 (VI)，一种非芳香类似物的合成。该合成中的关键步骤涉及从六氢吲哚和环己烯基乙酸中获得的酮酰胺 (IV) 本身的闭环。尝试将该顺序进一步扩展到使用 2H-5,6-二氢吡喃乙酸作为起始材料在后者的制备阶段遇到了失败。对图 III 所示的一种新的且不相关的逐步方法进行了研究，但在最终步骤中失败了。还简要描述了其他不成功的方法。
• Mondon, Chemische Berichte, 1959, vol. 92, p. 1461,1469
  作者：Mondon

  DOI：——

  日期：——
• THE SYNTHESIS OF ERYTHRINANE¹
  作者：B. Belleau

  DOI：10.1021/ja01118a531

  日期：1953.11
• An Improved Stereocontrolled Route to cis-Erythrinanes by Combined Intramolecular Strecker and Bruylants Reaction
  作者：Eberhard Reimann、Christian Ettmayr

  DOI：10.1007/s00706-004-0184-8

  日期：2004.9

  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.
• Syntheses of 14,15,16,17-Tetrahydroerythrinane^1,2
  作者：V. Boekelheide、Marcel Müller、J. Jack、T. T. Grossnickle、M. Chang

  DOI：10.1021/ja01524a035

  日期：1959.8