2'-ethylspiro[cyclohexane-1,3'-3H-indole] | 210557-50-9

• 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'-ethylspiro[cyclohexane-1,3'-3H-indole]
• 英文别名: 2'-ethylspiro(cyclohexan-1,3'-3'H-indole)；2'-Ethylspiro[cyclohexane-1,3'-indole]
• CAS: 210557-50-9
• 化学式: C₁₅H₁₉N
• 分子量: 213.323
• InChiKey: RSUXVDZOLLVSOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2'-ethylspiro[cyclohexane-1,3'-3H-indole] 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以78%的产率得到2'-ethylspiro[cyclohexane-1,3'-indoline]
  参考文献：
  名称：

  New Hexahydrocarbazoles and Spiro Indoles, and Their Affinity for D2 Dopamine and 5-HT2A Serotonin Receptors.

  摘要：

  在寻找新型非典型抗精神病药物的过程中，介绍了由 3-（二甲基氨基）丙基链 N 取代的新型六氢咔唑和螺吲哚的合成及其对 D2 和 5-HT2A 受体亲和力的体外评估结果。

  DOI：

  10.1248/cpb.47.1006
• 作为产物：
  描述：

  乙酰基环己烷 在 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 12.0h， 生成 2'-ethylspiro[cyclohexane-1,3'-3H-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.
• New Hexahydrocarbazoles and Spiro Indoles, and Their Affinity for D2 Dopamine and 5-HT2A Serotonin Receptors.
  作者：Franco FERNANDEZ、Xerardo GARCIA-MERA、Gonzalo RODRIGUEZ、Anahi URRUTIA

  DOI：10.1248/cpb.47.1006

  日期：——

  In a search for novel atypical antipsychotics, the synthesis of new hyxahydrocarbazoles and spiro indoles N-substituted with a 3-(dimethylamino)propyl chain is descrived, together with the results of an in vitro evaluation of their affinities for D2 and 5-HT2A receptors.

  在寻找新型非典型抗精神病药物的过程中，介绍了由 3-（二甲基氨基）丙基链 N 取代的新型六氢咔唑和螺吲哚的合成及其对 D2 和 5-HT2A 受体亲和力的体外评估结果。