2-(3-苯基-丙基)-环庚酮 | 101276-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3-苯基-丙基)-环庚酮
• 英文名称: 2-(3-phenyl-propyl)-cycloheptanone
• 英文别名: 2-(3-Phenyl-propyl)-cycloheptanon；2-(3-Phenylpropyl)cycloheptan-1-one
• CAS: 101276-70-4
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: OYOYHGSYTSFSAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  2-(3-苯基-丙基)-环庚酮 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Stereoselectivities of Nucleophilic Additions to Cycloheptanones. Experimental and Theoretical Studies and General Purpose Force Field for the Prediction of Nucleophilic Addition Stereoselectivities

  摘要：

  The selectivities of nucleophilic additions of ethyl, vinyl, and ethynyllithium and Grignard reagents to a 2-(3'-phenylpropyl)cycloheptanone were investigated experimentally. In all cases, cis-cycloheptanol was formed preferentially (40:1-6:1). Theoretical studies were performed on the stereoselectivities of nucleophilic additions of hydride and ethynyllithium reagents to cycloheptanones. An empirical force field for transition states of hydride and ethynyl reagents was used for transition-state geometries and conformational searches. Quantum mechanical calculations on HLi addition to cycloheptanones were compared to the corresponding cyclohexanone calculations. These results show that the formation of 2-alkyl-substituted cis-cycloheptanols is preferred for all nucleophiles studied as a result of torsional and steric effects in the transition states of these reactions.

  DOI：

  10.1021/jo971627b
• 作为产物：
  描述：

  cycloheptanone dimethylhydrazone 在 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(3-苯基-丙基)-环庚酮
  参考文献：
  名称：

  Stereoselectivities of Nucleophilic Additions to Cycloheptanones. Experimental and Theoretical Studies and General Purpose Force Field for the Prediction of Nucleophilic Addition Stereoselectivities

  摘要：

  The selectivities of nucleophilic additions of ethyl, vinyl, and ethynyllithium and Grignard reagents to a 2-(3'-phenylpropyl)cycloheptanone were investigated experimentally. In all cases, cis-cycloheptanol was formed preferentially (40:1-6:1). Theoretical studies were performed on the stereoselectivities of nucleophilic additions of hydride and ethynyllithium reagents to cycloheptanones. An empirical force field for transition states of hydride and ethynyl reagents was used for transition-state geometries and conformational searches. Quantum mechanical calculations on HLi addition to cycloheptanones were compared to the corresponding cyclohexanone calculations. These results show that the formation of 2-alkyl-substituted cis-cycloheptanols is preferred for all nucleophiles studied as a result of torsional and steric effects in the transition states of these reactions.

  DOI：

  10.1021/jo971627b

文献信息

• Gutsche et al., Journal of the American Chemical Society, 1957, vol. 79, p. 4441,4446
  作者：Gutsche et al.

  DOI：——

  日期：——