(1-Hydroxy-3-methyl-cyclohex-2-enyl)-phenyl-acetonitrile | 63064-16-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1-Hydroxy-3-methyl-cyclohex-2-enyl)-phenyl-acetonitrile
• 英文别名: 2-(1-Hydroxy-3-methylcyclohex-2-en-1-yl)-2-phenylacetonitrile
• CAS: 63064-16-4
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: VLIJZDRMVUWMDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙腈 、 3-甲基-2-环己烯-1-酮 生成 (1-Hydroxy-3-methyl-cyclohex-2-enyl)-phenyl-acetonitrile
  参考文献：
  名称：

  ROUX-SCHMITT M.-C.; WARTSKI L.; SEYDEN-PENNE J., SYNTH. COMMUN., 1981, 11, NO 2, 85-94

  摘要：

  DOI：

文献信息

• Roux-Schmitt, Marie-Claude; Wartski, Lya; Seyden-Penne, J., Synthetic Communications, 1981, vol. 11, # 2, p. 85 - 94
  作者：Roux-Schmitt, Marie-Claude、Wartski, Lya、Seyden-Penne, J.

  DOI：——

  日期：——
• 1,2- vs 1,4-Regioselectivity of Lithiated Phenylacetonitrile toward α,β-Unsaturated Carbonyl Compounds. 2. Relation between the Regioselectivity and the Structure of the Species in Solution
  作者：Tekla Strzalko、Jacqueline Seyden-Penne、Lya Wartski、Jacques Corset、Martine Castella-Ventura、Françoise Froment

  DOI：10.1021/jo9715175

  日期：1998.5.1

  In THF and THF-toluene media, the reaction of lithiated phenylacetonitrile (1) with benzylide-neacetone (5), at low temperature, led to the same ratio of 1,2- and 1,4-adducts after 5 or 30 min of reaction time. The concentrations of the monomeric bridged ion pair 2 preferentially formed in THF and of the dimer of ion pairs 4 predominating in media that favor association such as TKF-toluene solvent mixtures were measured from the IR-integrated intensities of the v (C=N) bands. These concentrations were quantitatively related to the concentrations of the 1,2- and 1,4-adducts, respectively. All these results evidence the kinetic control of this reaction. Intermediate complexes that take into account the peculiar geometries of the monomer 2 and the dimer 4 are proposed to interpret the different regioselectivities observed with 5. This study is extended to cyclic alpha-enones and cinnamaldehyde. Similar trends hold for the former, while cinnamaldehyde always leads to 1,2-addition. The formation of intermediate complexes allows us to rationalize the cinnamaldehyde behavior but is insufficient to explain the 1,4-addition with cyclic alpha-enones lying in an s-trans conformation.
• SAUVETRE R.; SEYDEN-PENNE J., TETRAHEDRON LETT., 1976, NO 44, 3949-3952
  作者：SAUVETRE R.、 SEYDEN-PENNE J.

  DOI：——

  日期：——
• ROUX-SCHMITT M.-C.; WARTSKI L.; SEYDEN-PENNE J., SYNTH. COMMUN., 1981, 11, NO 2, 85-94
  作者：ROUX-SCHMITT M.-C.、 WARTSKI L.、 SEYDEN-PENNE J.

  DOI：——

  日期：——