trans-1,2-diphenylbicyclo[3.1.0.0^2,4]hexane

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: trans-1,2-diphenylbicyclo[3.1.0.0^2,4]hexane
• 英文别名: (1S,2S,4S,5S)-1,2-diphenyltricyclo[3.1.0.02,4]hexane
• 化学式: C₁₈H₁₆
• 分子量: 232.325
• InChiKey: WVCJJZUUPYLMLJ-WNRNVDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  5.0
• 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-1,2-diphenylbicyclo[3.1.0.0^2,4]hexane 以 四氢呋喃 为溶剂， 反应 8.0h， 以91%的产率得到1,2-diphenylcyclohexa-1,4-diene
  参考文献：
  名称：

  Novel Ene Trimerization of 1-Phenylcyclopropene

  摘要：

  1-Phenylcyclopropene (1) was synthesized by treatment of 1,1,2-tribromo-2-phenylcyclopropane (2) with 2.5 equiv of methyllithium followed by protonation. Compound 1 underwent ene dimerization to form ene dimer 5 followed by ene reaction with monomer 1 (enophile) to give an ene trimer 6. Both of these two ene reactions derived endo transition states. In the meantime, the [2+2] adduct, trans1,2-diphenylbicyclo[3.1.0.0(2,4)]hexane (7), was also formed. When the adduct 7 was heated at THF refluxing temperature, 1,2-diphenylcyclohexa-1,4-diene (8) was obtained. Compound 8 was treated with DDQ to yield o-diphenylbenzene.

  DOI：

  10.1021/jo048889f
• 作为产物：
  描述：

  1,1,2-tribromo-2-phenylcyclopropane 在 甲基锂 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 trans-1,2-diphenylbicyclo[3.1.0.0^2,4]hexane
  参考文献：
  名称：

  Novel Ene Trimerization of 1-Phenylcyclopropene

  摘要：

  1-Phenylcyclopropene (1) was synthesized by treatment of 1,1,2-tribromo-2-phenylcyclopropane (2) with 2.5 equiv of methyllithium followed by protonation. Compound 1 underwent ene dimerization to form ene dimer 5 followed by ene reaction with monomer 1 (enophile) to give an ene trimer 6. Both of these two ene reactions derived endo transition states. In the meantime, the [2+2] adduct, trans1,2-diphenylbicyclo[3.1.0.0(2,4)]hexane (7), was also formed. When the adduct 7 was heated at THF refluxing temperature, 1,2-diphenylcyclohexa-1,4-diene (8) was obtained. Compound 8 was treated with DDQ to yield o-diphenylbenzene.

  DOI：

  10.1021/jo048889f

文献信息

• The Crossed [2+2] Cycloaddition of 1-Phenylcyclopropene and 1-Bromo-2-phenylcyclopropene
  作者：Gon-Ann Lee、Wen-Chieh Wang、Shih-Fen Jiang、Chih-Yi Chang、Ru-Ting Tsai

  DOI：10.1021/jo901636k

  日期：2009.10.16

  1-Bromo-2-phenylcyclopropene (2) underwent [2+2] dimerization to generate 1,2-dibromo-4,5-diphenyltricyclo[3.1.0.0(2,4)]hexane (5), which was heated to form 1,2-dibromo-4,5-diphenyleyclohexa-1,4-diene (6) followed by oxidation to yield 4',5'-dibromo-o-terphenyl (7). o-Terphenyl 7 could be synthesized in one-pot reactions from 1, 1,2-tribromocyclopropane (3). When cyclopropane 3 was treated with 1.5 equiv of methyllithium followed by slowly adding the proton source, crossed [2+2] adduct 8 was isolated in 40% yield. Compound 8 was heated and oxidated to produce 4'-bromo-o-terphenyl (11).
• Novel Ene Trimerization of 1-Phenylcyclopropene
  作者：Gon-Ann Lee、Chih-Yi Chang

  DOI：10.1021/jo048889f

  日期：2004.12.1

  1-Phenylcyclopropene (1) was synthesized by treatment of 1,1,2-tribromo-2-phenylcyclopropane (2) with 2.5 equiv of methyllithium followed by protonation. Compound 1 underwent ene dimerization to form ene dimer 5 followed by ene reaction with monomer 1 (enophile) to give an ene trimer 6. Both of these two ene reactions derived endo transition states. In the meantime, the [2+2] adduct, trans1,2-diphenylbicyclo[3.1.0.0(2,4)]hexane (7), was also formed. When the adduct 7 was heated at THF refluxing temperature, 1,2-diphenylcyclohexa-1,4-diene (8) was obtained. Compound 8 was treated with DDQ to yield o-diphenylbenzene.