2'-allyl-2'-methylspiro(cyclohexan-1,3'-3'H-indole)

• 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'-allyl-2'-methylspiro(cyclohexan-1,3'-3'H-indole)
• 英文别名: 2-methyl-2-prop-2-enylspiro[1H-indole-3,1'-cyclohexane]
• 化学式: C₁₇H₂₃N
• 分子量: 241.376
• InChiKey: PZAGHPMGCLKVGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  乙酰基环己烷 在 溶剂黄146 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 13.0h， 生成 2'-allyl-2'-methylspiro(cyclohexan-1,3'-3'H-indole)
  参考文献：
  名称：

  Synthesis of 2‘-Alkylspiro[2-X-cyclohexan-1,3‘-3‘H-indole] (X = H; X = CH₃) by an Unexpected Reaction between an Organomagnesium Halide and 2‘-Methylspiro[2-X-cyclohexan-1,3‘-3‘H-indole]. X-ray Structure of a Fluorescent Dimeric Compound

  摘要：

  The reaction of 2'-methylspiro[cyclohexan-1,3'-3'H-indole] (1a) with methylmagnesium iodide gives 2'-ethyl-, 2'-isopropyl-, and 2'-tert-butylspiro[cyclohexan-1,3'-3'H-indole] as the unexpected 2'-methyl insertion products; their presence and ratio are dependent upon the reaction conditions. Influence of a methyl substituent in 2'-methylspiro[2-methylcyclohexan-1,3'-3'H-indole] (1b) on the reaction with methylmagnesium iodide has been analyzed; the 2'-ethyl (2b) and 2'-isopropyl (3b) derivatives were obtained as the insertion products together with a luminescent compound that was identified by X-ray diffraction analysis as meso-(1R,2S),(1S,2R)-alpha,beta-di{(2'-(spiro[2 -methylcyclohexan-1,3'-3'H-indolyl]}ethene (10). The reaction of 1a or 1b with some active organomagnesium halides (allyl or benzyl) afforded the 2'-methyl-2'-alkyl-3'H-indole derivative (allyl, 5a or 5b; benzyl, 6a) as an apparent addition product. The reaction possibly occurs through a mechanism of radical intermediates.

  DOI：

  10.1021/jo980072x

文献信息

• Synthesis of 2‘-Alkylspiro[2-X-cyclohexan-1,3‘-3‘<i>H</i>-indole] (X = H; X = CH₃) by an Unexpected Reaction between an Organomagnesium Halide and 2‘-Methylspiro[2-X-cyclohexan-1,3‘-3‘<i>H</i>-indole]. X-ray Structure of a Fluorescent Dimeric Compound
  作者：J. Gonzalo Rodríguez、Anahí Urrutia、J. Eugenio de Diego、M. Paz Martínez-Alcazar、I. Fonseca

  DOI：10.1021/jo980072x

  日期：1998.6.1

  The reaction of 2'-methylspiro[cyclohexan-1,3'-3'H-indole] (1a) with methylmagnesium iodide gives 2'-ethyl-, 2'-isopropyl-, and 2'-tert-butylspiro[cyclohexan-1,3'-3'H-indole] as the unexpected 2'-methyl insertion products; their presence and ratio are dependent upon the reaction conditions. Influence of a methyl substituent in 2'-methylspiro[2-methylcyclohexan-1,3'-3'H-indole] (1b) on the reaction with methylmagnesium iodide has been analyzed; the 2'-ethyl (2b) and 2'-isopropyl (3b) derivatives were obtained as the insertion products together with a luminescent compound that was identified by X-ray diffraction analysis as meso-(1R,2S),(1S,2R)-alpha,beta-di(2'-(spiro[2 -methylcyclohexan-1,3'-3'H-indolyl]}ethene (10). The reaction of 1a or 1b with some active organomagnesium halides (allyl or benzyl) afforded the 2'-methyl-2'-alkyl-3'H-indole derivative (allyl, 5a or 5b; benzyl, 6a) as an apparent addition product. The reaction possibly occurs through a mechanism of radical intermediates.