3,4-二苯基己二腈 | 18891-12-8

• 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
• 中文名称: 3,4-二苯基己二腈
• 英文名称: d,l-3,4-diphenyladiponitrile
• 英文别名: racem.-3,4-diphenyl-adiponitrile；racem.-3,4-Diphenyl-adiponitril；(3S,4S)-3,4-diphenylhexanedinitrile
• CAS: 18891-12-8；84679-83-4；86071-29-6；86117-67-1；108391-55-5
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: HDZULEGFVXCPDV-QZTJIDSGSA-N

物化性质

• 沸点：
  470.2±45.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.58
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,4-二苯基己二腈 在 盐酸 、 barium dihydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 dimethyl (3SR,4SR)-3,4-diphenylhexanedioate
  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
• 作为产物：
  描述：

  (S,S)-(+)-2,3-二苯基丁二酸 在 lithium aluminium tetrahydride 、 esterification agent 、 tosylating agent 作用下， 生成 3,4-二苯基己二腈
  参考文献：
  名称：

  含有顺式-4b，5,6,10b，11,12-六氢丙烯和顺式-4b，5,9b，10-四氢茚并[2,1- a ]-茚亚基为手性的冠醚的合成和对映体识别中心

  摘要：

  已经确定了C 2对称性的二醇（–）-（1）和（+）-（4）的绝对构型，并且新型旋光冠醚（–）-（3）和（+已经研究了分别由（-）-（1）和（+）-（4）制备的）-（6）。

  DOI：

  10.1039/c39860001675

文献信息

• Knunjanz; Wjasankin, Doklady Akademii Nauk SSSR, 1957, vol. 113, p. 112
  作者：Knunjanz、Wjasankin

  DOI：——

  日期：——
• Enantioselective synthesis of dimethyl 3,4-diphenyladipate by electroreductive hydrocoupling of chiral N-trans-cinnamoyl-2-oxazolidones
  作者：Naoki Kise、Mitsuaki Echigo、Tatsuya Shono

  DOI：10.1016/s0040-4039(00)73190-x

  日期：1994.3

  Dimethyl(3R,4R)- and (3S,4S)-diphenyladipate were synthesized enantioselectively by electroreductive intermolecular hydrocoupling of chiral N-trans-cinnamoyl-2-oxazolidones and subsequent methanolysis.
• Degrand, Chantal; Mora, Raymond; Lund, Henning, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1983, vol. 37, # 5, p. 429 - 436
  作者：Degrand, Chantal、Mora, Raymond、Lund, Henning

  DOI：——

  日期：——
• NAEMURA KOICHIRO; KOMATSU MASANORI; ADACHI KEIICHI; CHIKAMATSU HIROAKI, J. CHEM. SOC. CHEM. COMMUN.,(1986) N 22, 1675-1676
  作者：NAEMURA KOICHIRO、 KOMATSU MASANORI、 ADACHI KEIICHI、 CHIKAMATSU HIROAKI

  DOI：——

  日期：——