4-methyl-3-(1-methyl-1H-indol-3-yl)-1-phenylpentan-1-one | 1221071-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-3-(1-methyl-1H-indol-3-yl)-1-phenylpentan-1-one
• 英文别名: 4-Methyl-3-(1-methylindol-3-yl)-1-phenylpentan-1-one；4-methyl-3-(1-methylindol-3-yl)-1-phenylpentan-1-one
• CAS: 1221071-44-8
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: XCIRZWPAUAQBNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 1-苯基-4-甲基-1-戊炔-3醇 在 甲醇 、 platinum(II) chloride 作用下， 反应 24.0h， 以57%的产率得到4-methyl-3-(1-methyl-1H-indol-3-yl)-1-phenylpentan-1-one
  参考文献：
  名称：

  Platinum-Catalyzed Multi-Step Reaction of Propargyl Alcohols withN-Heteroaromatics

  摘要：

  AbstractN‐Methyl indole reacts with but‐2‐yn‐1‐ol in the presence of PtCl2 in MeOH giving indole derivatives having a substituted 3‐oxobutyl group at the 3‐position in good yield. Under the reaction conditions, various substituted indoles and substituted propargyl alcohols are successfully involved in the reaction giving the corresponding addition products in good to moderate yields. The catalytic reaction can be further extended to N‐phenyl pyrrole. In the present multi‐step reaction, PtCl2 likely plays dual roles: as the catalyst for the rearrangement of propargyl alcohols to the corresponding alkenyl ketones and as the catalyst for the addition of indoles to the alkenyl ketones. Experimental evidence is provided to support the proposed mechanism.

  DOI：

  10.1002/asia.200900318

文献信息

• Platinum-Catalyzed Multi-Step Reaction of Propargyl Alcohols with<i>N</i>-Heteroaromatics
  作者：Sivakolundu Bhuvaneswari、Masilamani Jeganmohan、Chien-Hong Cheng

  DOI：10.1002/asia.200900318

  日期：2010.1.4

  AbstractN‐Methyl indole reacts with but‐2‐yn‐1‐ol in the presence of PtCl2 in MeOH giving indole derivatives having a substituted 3‐oxobutyl group at the 3‐position in good yield. Under the reaction conditions, various substituted indoles and substituted propargyl alcohols are successfully involved in the reaction giving the corresponding addition products in good to moderate yields. The catalytic reaction can be further extended to N‐phenyl pyrrole. In the present multi‐step reaction, PtCl2 likely plays dual roles: as the catalyst for the rearrangement of propargyl alcohols to the corresponding alkenyl ketones and as the catalyst for the addition of indoles to the alkenyl ketones. Experimental evidence is provided to support the proposed mechanism.