3ref,4trans-Diphenyl-cyclopentanol-(1cis) | 216484-78-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3ref,4trans-Diphenyl-cyclopentanol-(1cis)
• 英文别名: (3R,4R)-3,4-diphenylcyclopentan-1-ol
• CAS: 216484-78-5
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: UCWFNBPKKUTYLY-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3ref,4trans-Diphenyl-cyclopentanol-(1cis) 、 氢溴酸 生成 (4-Bromo-2-phenylcyclopentyl)benzene
  参考文献：
  名称：

  KREJTSBERGA YA. N.; NEJLAND O. YA.; KAMPAR V. EH., LATVRSR ZINAT. ASAD. VESTIS. KIM. SEV., IZV. AN LATVSSR. CEP. XIM., 1978,+

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-N-[3-phenyl-2-(E)-propenoyl]-4-isopropyl-1,3-oxazolidine-2-thione 在 sodium tetrahydroborate 、 四乙基对甲苯磺酸铵 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.5h， 生成 3ref,4trans-Diphenyl-cyclopentanol-(1cis)
  参考文献：
  名称：

  Stereoselective Hydrocoupling of Optically Active 3-trans-Cinnamoyloxazolidinones by Electroreduction

  摘要：

  Reductive hydrocoupling of chiral 3-trans-cinnamoyloxazolidinones was studied by an electro chemical method. The electroreduction was performed conveniently at a constant current using an undivided cell. The stereoselectivity of the hydrodimers was strongly affected by the electrolyte employed. Electroreduction of (S)-4-isobutyl-3-trans-cinnamoyloxazolidinone 1a in 0.3 M Et4NOTs/AN gave a mixture of two diastereomers of all-trans cyclized hydrodimer 2a, and the selectivity was R,S,R/S,R,S = 85:15. On the other hand, the reduction of 1a in 1.7 M LiClO4/THF afforded a diastereomeric mixture of hydrodimers in a selectivity of R,R/S,S/R,S = 5:52:43. The stereoselectivities were explained by considering stable conformations of intermediate anion radicals, that is, syn-Z type for naked anion radicals and anti-Z type for lithiated anion radicals. Semiempirical calculations also supported this hypothesis. Electroreductions of (S)-4-isobutyl-3-cis-cinnamoyloxazolidinone and (S)-4-isobutyl-3-phenylpropioloyloxazolidinone gave 2a in the same stereoselectivity as electroreduction of 1a did. The electroreductive hydrocoupling was not inhibited by para and meta substitution on the aryl group of 3-trans-cinnamoyloxazolidinones. An ortho substitution, however, hindered the hydrocoupling and lowered the stereoselectivity of the hydrodimers. Electroreduction of 3-trans-cinnamoyloxazolidinethione and thiazolidinethione gave trans-3,4-diphenylcyclopentanone as a product, and the stereoselectivities were similar to that obtained from the corresponding oxazolidinone.

  DOI：

  10.1021/jo981231f