1-(3-(4-acetylphenyl)propyl)indole | 253307-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-(4-acetylphenyl)propyl)indole
• CAS: 253307-99-2
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: YDZSWJHFGHXBJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 1-(3-(4-acetylphenyl)propyl)indole 在 三氯氧磷 作用下， 反应 2.0h， 以65%的产率得到3-formyl-1-(3-(4-acetylphenyl)propyl)indole
  参考文献：
  名称：

  Synthesis, structure and AM1 conformational study of [3]paracyclo[3](1,3)indolophane, a novel chiral cyclophane

  摘要：

  The title compound 5 was synthesized in seven steps with an overall yield of 22%. The two bridges were formed by a conjugate addition of indole to a Michael acceptor and by an intramolecular N-alkylation, respectively. A dynamic NMR study revealed the presence of a conformational process with an activation barrier of 10.9+/-0.2 kcal/mol, which was assigned to a ring flipping process that interconverts two enantiomeric sets of equilibrating bridge conformers. In the crystal structure of 5, both bridges adopt the pseudo-chair conformation, in accord with the lowest energy conformation identified by an AM1 conformational search. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00792-9
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 在 sodium hydroxide 、 三氯化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-(3-(4-acetylphenyl)propyl)indole
  参考文献：
  名称：

  Synthesis, structure and AM1 conformational study of [3]paracyclo[3](1,3)indolophane, a novel chiral cyclophane

  摘要：

  The title compound 5 was synthesized in seven steps with an overall yield of 22%. The two bridges were formed by a conjugate addition of indole to a Michael acceptor and by an intramolecular N-alkylation, respectively. A dynamic NMR study revealed the presence of a conformational process with an activation barrier of 10.9+/-0.2 kcal/mol, which was assigned to a ring flipping process that interconverts two enantiomeric sets of equilibrating bridge conformers. In the crystal structure of 5, both bridges adopt the pseudo-chair conformation, in accord with the lowest energy conformation identified by an AM1 conformational search. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00792-9

文献信息

• Synthesis, structure and AM1 conformational study of [3]paracyclo[3](1,3)indolophane, a novel chiral cyclophane
  作者：Graham J. Bodwell、Jiang Li、David O. Miller

  DOI：10.1016/s0040-4020(99)00792-9

  日期：1999.11

  The title compound 5 was synthesized in seven steps with an overall yield of 22%. The two bridges were formed by a conjugate addition of indole to a Michael acceptor and by an intramolecular N-alkylation, respectively. A dynamic NMR study revealed the presence of a conformational process with an activation barrier of 10.9+/-0.2 kcal/mol, which was assigned to a ring flipping process that interconverts two enantiomeric sets of equilibrating bridge conformers. In the crystal structure of 5, both bridges adopt the pseudo-chair conformation, in accord with the lowest energy conformation identified by an AM1 conformational search. (C) 1999 Elsevier Science Ltd. All rights reserved.