1-[(1S)-1-naphthalen-1-ylethyl]-1-phenylhydrazine | 880647-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(1S)-1-naphthalen-1-ylethyl]-1-phenylhydrazine
• CAS: 880647-69-8
• 化学式: C₁₈H₁₈N₂
• 分子量: 262.354
• InChiKey: MRMNUQSWMGLZTD-AWEZNQCLSA-N

物化性质

• 沸点：
  440.6±24.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(1S)-1-naphthalen-1-ylethyl]-1-phenylhydrazine 、 4-chloro-2-methyl-butanal 以 异丙醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids

  摘要：

  Facile access to optically active pyrroloindoles by Fischer-type pyrroloindole synthesis is investigated. The reaction using chiral hydrazines prepared from commercially available chiral amines proceeded with diastereoselective cyclization (up to 70% de), and a short-step conversion of the cycloadducts to (-)-desoxyeseroline and pyrroloindole alkaloids was achieved.

  DOI：

  10.3987/com-05-s(k)71
• 作为产物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 在 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 盐酸 、 lithium aluminium tetrahydride 、 sodium t-butanolate 、 sodium nitrite 作用下， 以 乙醚 、 甲苯 、 苯 为溶剂， 生成 1-[(1S)-1-naphthalen-1-ylethyl]-1-phenylhydrazine
  参考文献：
  名称：

  Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids

  摘要：

  Facile access to optically active pyrroloindoles by Fischer-type pyrroloindole synthesis is investigated. The reaction using chiral hydrazines prepared from commercially available chiral amines proceeded with diastereoselective cyclization (up to 70% de), and a short-step conversion of the cycloadducts to (-)-desoxyeseroline and pyrroloindole alkaloids was achieved.

  DOI：

  10.3987/com-05-s(k)71

文献信息

• Exploration of the interrupted Fischer indolization reaction
  作者：Alex W. Schammel、Ben W. Boal、Liansuo Zu、Tehetena Mesganaw、Neil K. Garg

  DOI：10.1016/j.tet.2010.02.050

  日期：2010.6

  molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. The method is convergent, mild, operationally simple, broad in scope, and can be used to access enantioenriched products. In addition, our approach is amenable to the synthesis of furoindoline

  已经开发了一种收敛方法来访问存在于大量生物活性分子中的稠合二氢吲哚环系统。该策略涉及肼与潜在醛的缩合，以通过中断的 Fischer 吲哚化序列最终提供含二氢吲哚的产物。该方法收敛、温和、操作简单、适用范围广，可用于获得对映体富集的产品。此外，我们的方法适用于呋喃二氢吲哚和吡咯烷二氢吲哚天然产物的合成，如 physovenine 和 debromoflustramine B 的简洁正式全合成所证明的那样。 该策略可能会合成更复杂的目标，如公社生物碱。
• Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids
  作者：Atsushi Nishida、Satoru Ushigome、Ayako Sugimoto、Shigeru Arai

  DOI：10.3987/com-05-s(k)71

  日期：——

  Facile access to optically active pyrroloindoles by Fischer-type pyrroloindole synthesis is investigated. The reaction using chiral hydrazines prepared from commercially available chiral amines proceeded with diastereoselective cyclization (up to 70% de), and a short-step conversion of the cycloadducts to (-)-desoxyeseroline and pyrroloindole alkaloids was achieved.