1-(3-chloro-1-oxopropyl)-4-(3-bromopropyl)benzene | 253308-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-chloro-1-oxopropyl)-4-(3-bromopropyl)benzene
• 英文别名: 1-[4-(3-Bromopropyl)phenyl]-3-chloropropan-1-one；1-[4-(3-bromopropyl)phenyl]-3-chloropropan-1-one
• CAS: 253308-01-9
• 化学式: C₁₂H₁₄BrClO
• 分子量: 289.6
• InChiKey: GPJKORBOWABKKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-chloro-1-oxopropyl)-4-(3-bromopropyl)benzene 在 sodium tetrahydroborate 、 乙酸酐 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (+/-)-3-(3-(4-(3-bromopropyl)phenyl)-3-hydroxypropyl)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 、 3-氯丙酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以98%的产率得到1-(3-chloro-1-oxopropyl)-4-(3-bromopropyl)benzene
  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.