2-(1-phenylethyl)-1H-indole-3-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(1-phenylethyl)-1H-indole-3-carbaldehyde
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: VSEDWUWRWKXAKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-phenylethyl)-1H-indole-3-carbaldehyde 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以50%的产率得到
  参考文献：
  名称：

  Cobalt-Catalyzed Enantioselective Directed C–H Alkylation of Indole with Styrenes

  摘要：

  A cobalt-chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C-C reductive elimination steps.

  DOI：

  10.1021/ol503119z
• 作为产物：
  描述：

  2-苯基丙酸 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 草酰氯 、 三乙基硼 、 三正丁基氢锡 、 potassium tri-sec-butyl-borohydride 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 50.0h， 生成 2-(1-phenylethyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Synthesis of Ellipticine:  A Radical Cascade Protocol to Aryl- and Heteroaryl-Annulated[b]carbazoles

  摘要：

  Imidoyl selanides, synthesized from amides, have been used as radical precursors of imidoyl radicals in cascade reactions. The novel radical cascade has been developed for the simple synthesis of the medicinally important aryl-annulated[b]-carbazoles. The protocol has been exemplified with the high-yielding total synthesis of the anticancer alkaloid ellipticine.

  DOI：

  10.1021/jo0519920

文献信息

• Cobalt-Catalyzed Enantioselective Directed C–H Alkylation of Indole with Styrenes
  作者：Pin-Sheng Lee、Naohiko Yoshikai

  DOI：10.1021/ol503119z

  日期：2015.1.2

  A cobalt-chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C-C reductive elimination steps.
• Synthesis of Ellipticine:  A Radical Cascade Protocol to Aryl- and Heteroaryl-Annulated[<i>b</i>]carbazoles
  作者：Jan M. Pedersen、W. Russell Bowman、Mark R. J. Elsegood、Anthony J. Fletcher、Peter J. Lovell

  DOI：10.1021/jo0519920

  日期：2005.12.1

  Imidoyl selanides, synthesized from amides, have been used as radical precursors of imidoyl radicals in cascade reactions. The novel radical cascade has been developed for the simple synthesis of the medicinally important aryl-annulated[b]-carbazoles. The protocol has been exemplified with the high-yielding total synthesis of the anticancer alkaloid ellipticine.