1,5,5-trimethyl-3-(1'-methylindol-3'-yl)cyclohex-1-ene

• 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: 1,5,5-trimethyl-3-(1'-methylindol-3'-yl)cyclohex-1-ene
• 英文别名: 1-Methyl-3-(3,5,5-trimethylcyclohex-2-en-1-yl)indole
• 化学式: C₁₈H₂₃N
• 分子量: 253.387
• InChiKey: BMZBKOPOPFNQKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 acetic acid 3,5,5-trimethylcyclohex-2-enyl ester 在 2 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到1,5,5-trimethyl-3-(1'-methylindol-3'-yl)cyclohex-1-ene
  参考文献：
  名称：

  Molybdenum(II)-Catalyzed Allylation of Electron-Rich Aromatics and Heteroaromatics

  摘要：

  The stable, readily available molybdenum(II) complexes [Mo(CO)(4)Br-2](2) (B) and Mo(CO)(3)(MeCN)(2)(SnCl3)Cl (C) have been found to catalyze C-C bond-forming allylic substitution with electron-rich aromatics (e.g., 15 + PhOMe --> 62) and heteroaromatics (e.g., 15 + 36 --> 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.

  DOI：

  10.1021/jo982178y

文献信息

• Molybdenum(II)-Catalyzed Allylation of Electron-Rich Aromatics and Heteroaromatics
  作者：Andrei V. Malkov、Stuart L. Davis、Ian R. Baxendale、William L. Mitchell、Pavel Kočovský

  DOI：10.1021/jo982178y

  日期：1999.4.1

  The stable, readily available molybdenum(II) complexes [Mo(CO)(4)Br-2](2) (B) and Mo(CO)(3)(MeCN)(2)(SnCl3)Cl (C) have been found to catalyze C-C bond-forming allylic substitution with electron-rich aromatics (e.g., 15 + PhOMe --> 62) and heteroaromatics (e.g., 15 + 36 --> 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.