trans-1-(E-1-Propenyl)-2-phenylcyclopropane | 130931-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-1-(E-1-Propenyl)-2-phenylcyclopropane
• 英文别名: (E)-1-Phenyl-2-<(E)-propenyl>cyclopropan；[(1S,2R)-2-[(E)-prop-1-enyl]cyclopropyl]benzene
• CAS: 130931-54-3
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: FKPOPTLEHBNNCJ-KAKUWJJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  trans-1-(E-1-Propenyl)-2-phenylcyclopropane 生成 (Z)-1-Phenyl-2-<(E)-propenyl>cyclopropan 、 trans-3-Methyl-4-phenylcyclopentene 、 cis-3-Methyl-4-phenylcyclopentene
  参考文献：
  名称：

  Stereochemistry of the Thermal Isomerizations of (1R,2S)-1-(E-1-Propenyl)-2-phenylcyclopropane to 3-Methyl-4-phenylcyclopentenes

  摘要：

  When (1R,2S)-trans-1-(E-1-propenyl)-2-phenylcyclopropane is heated at 234.4 degrees C in the gas phase, it is isomerized reversibly to its (1S,2R) enantiomer and to the enantiomers of cis-1-(E-1-propenyl)-2-phenylcyclopropane as the four isomers of 3-methyl-4-phenylcyclopentene are formed more slowly. Kinetic and stereochemical evidence indicates that this vinylcyclopropane to cyclopentene rearrangement takes place with the participation of all four possible stereochemically distinct reaction paths: the relative contributions are 44% si, 20% ar, 25% sr, and 11% ai. This stereochemical pattern is substantially similar to those determined previously for the rearrangements of three chiral trans-1-alkenyl-2-methylcyclopropanes, a result reinforcing the perception that the stereochemistry of the rearrangement is controlled neither by orbital symmetry factors nor by the relative moments of inertia or radical-stabilizing capacities of substituent groups.

  DOI：

  10.1021/jo00103a036
• 作为产物：
  描述：

  trans-(3-phenylcyclopropyl)methanol 在 aluminum oxide 、 3 A molecular sieve 、 仲丁基锂 、 pyridinium chlorochromate 作用下， 以 正己烷 为溶剂， 反应 21.5h， 生成 trans-1-(E-1-Propenyl)-2-phenylcyclopropane
  参考文献：
  名称：

  Stereochemistry of the Thermal Isomerizations of (1R,2S)-1-(E-1-Propenyl)-2-phenylcyclopropane to 3-Methyl-4-phenylcyclopentenes

  摘要：

  When (1R,2S)-trans-1-(E-1-propenyl)-2-phenylcyclopropane is heated at 234.4 degrees C in the gas phase, it is isomerized reversibly to its (1S,2R) enantiomer and to the enantiomers of cis-1-(E-1-propenyl)-2-phenylcyclopropane as the four isomers of 3-methyl-4-phenylcyclopentene are formed more slowly. Kinetic and stereochemical evidence indicates that this vinylcyclopropane to cyclopentene rearrangement takes place with the participation of all four possible stereochemically distinct reaction paths: the relative contributions are 44% si, 20% ar, 25% sr, and 11% ai. This stereochemical pattern is substantially similar to those determined previously for the rearrangements of three chiral trans-1-alkenyl-2-methylcyclopropanes, a result reinforcing the perception that the stereochemistry of the rearrangement is controlled neither by orbital symmetry factors nor by the relative moments of inertia or radical-stabilizing capacities of substituent groups.

  DOI：

  10.1021/jo00103a036

文献信息

• Fischer, Helmut; Hofmann, Josef, Chemische Berichte, 1991, vol. 124, # 5, p. 981 - 988
  作者：Fischer, Helmut、Hofmann, Josef

  DOI：——

  日期：——
• Stereochemistry of the Thermal Isomerizations of (1R,2S)-1-(E-1-Propenyl)-2-phenylcyclopropane to 3-Methyl-4-phenylcyclopentenes
  作者：John E. Baldwin、Samuel Bonacorsi

  DOI：10.1021/jo00103a036

  日期：1994.12

  When (1R,2S)-trans-1-(E-1-propenyl)-2-phenylcyclopropane is heated at 234.4 degrees C in the gas phase, it is isomerized reversibly to its (1S,2R) enantiomer and to the enantiomers of cis-1-(E-1-propenyl)-2-phenylcyclopropane as the four isomers of 3-methyl-4-phenylcyclopentene are formed more slowly. Kinetic and stereochemical evidence indicates that this vinylcyclopropane to cyclopentene rearrangement takes place with the participation of all four possible stereochemically distinct reaction paths: the relative contributions are 44% si, 20% ar, 25% sr, and 11% ai. This stereochemical pattern is substantially similar to those determined previously for the rearrangements of three chiral trans-1-alkenyl-2-methylcyclopropanes, a result reinforcing the perception that the stereochemistry of the rearrangement is controlled neither by orbital symmetry factors nor by the relative moments of inertia or radical-stabilizing capacities of substituent groups.