(trans-2,trans-3-diphenylcyclopropyl)cyclopropylmethanol | 117021-84-8

• 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-2,trans-3-diphenylcyclopropyl)cyclopropylmethanol
• 英文别名: (trans-2,trans-3-diphenyldicyclopropyl)methanol
• CAS: 117021-84-8
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: HRKLEHDDPPOYFB-ULNPTZJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (trans-2,trans-3-diphenylcyclopropyl)cyclopropylmethanol 在 硼烷四氢呋喃络合物 、 三氟化硼乙醚 作用下， 生成 (trans-2,trans-3-diphenylcyclopropyl)cyclopropylmethane
  参考文献：
  名称：

  Stabilization of carbinylcarbocation by and nucleophilic attack upon cyclopropyl and trans-2, trans-3-diphenylcyclopropyl rings. Reduction of (trans-2, trans-3-diphenylcyclopropyl)methanol and (trans-2, trans-3-diphenylcyclopropyl)cyclopropylmethanol

  摘要：

  (trans-2,trans-3-Diphenylcyclopropyl)methanol (R1OH) can be reduced to (trans-2,trans-3-diphenylcyclopropyl)methane with NaBH3CN in the presence of (PhO)3PMeI and (trans-2,trans-3-diphenylcyclopropyl)cyclopropylmethanol (R2OH) can be reduced to its hydrocarbon by BH3-BF3 without ring opening. Acid catalyzed H2O elimination from R2OH by CF3COOH is accompanied by concerted ring opening of the diphenylcyclopropyl ring with a late transition state, but S(N)2 iodiation of R2OH with (PhO)3PMeI results in concerted opening of the unsubstituted cyclopropyl ring. The trans-2,trans-3-diphenylcyclopropyl group is less effective than a simple cyclopropyl group in stabilizing an adjacent positive charge.

  DOI：

  10.1016/0040-4020(92)85003-w
• 作为产物：
  描述：

  trans-2,trans-3-diphenylcyclopropanecarboxaldehyde 以80%的产率得到
  参考文献：
  名称：

  CASTELLINO, ANGELO J.;BRUICE, THOMAS C., J. AMER. CHEM. SOC., 110,(1988) N 22, C. 7512-7519

  摘要：

  DOI：

文献信息

• Intermediates in the epoxidation of alkenes by cytochrome P-450 models. 2. Use of the trans-2,trans-3-diphenylcyclopropyl substituent in a search for radical intermediates
  作者：Angelo J. Castellino、Thomas C. Bruice

  DOI：10.1021/ja00230a039

  日期：1988.10

  Catalyse par les complexes: [(F 20 TPP)Fe(III)(Cl)], [(Cl 8 TPP)Fe(III)(Cl)], et [(Cl 8 TPP)Mn(III)(OH)]. (F 20 TPP=meso-tetrakis-pentafluorophenyl porphyrine, Cl 8 TPP=meso-tetrakis-[dichloro-2,6 phenyl] porphyrine)

  催化复合物：[(F 20 TPP)Fe(III)(Cl)]、[(Cl 8 TPP)Fe(III)(Cl)]等[(Cl 8 TPP)Mn(III)(OH)] . (F 20 TPP=meso-tetrakis-pentafluorophenyl porphyrine, Cl 8 TPP=meso-tetrakis-[dichloro-2,6 phenyl] porphyrine)