(2S,3S)-(+)-2,3-Diphenylbutane-1,4-ditosylate | 139628-56-1

• 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: (2S,3S)-(+)-2,3-Diphenylbutane-1,4-ditosylate
• 英文别名: [(2S,3S)-4-(4-methylphenyl)sulfonyloxy-2,3-diphenylbutyl] 4-methylbenzenesulfonate
• CAS: 139628-56-1
• 化学式: C₃₀H₃₀O₆S₂
• 分子量: 550.697
• InChiKey: PFXFMAXBCFUHFW-LOYHVIPDSA-N

物化性质

• 沸点：
  704.6±60.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-(+)-2,3-Diphenylbutane-1,4-ditosylate 在 barium dihydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 racem.-3,4-diphenyl-adipic acid
  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：

  2,3-二苯基琥珀酸二乙基酯 在 吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 水 、 碘 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 50.0h， 生成 (2S,3S)-(+)-2,3-Diphenylbutane-1,4-ditosylate
  参考文献：
  名称：

  C2 对称 3,4-二苯基吡咯烷的便​​捷合成方法

  摘要：

  介绍了合成外消旋和对映体纯的3,4-二苯基吡咯烷衍生物的便捷方法，其关键步骤包括使用TiCl4/Et3N进行乙基苯乙酸酯的氧化偶联，以及用NaBH4/I2试剂对dl-2,3-二苯基琥珀酸或相应的环状亚胺进行还原。

  DOI：

  10.1055/s-2000-6404

文献信息

• 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.
• Design and synthesis of novel chiral pyrrolidine-based diamines with C2-symmetry
  作者：Makoto Nakajima、Kiyoshi Tomioka、Kenji Koga

  DOI：10.1016/s0040-4020(01)80176-9

  日期：1993.1

  Novel chiral pyrrolidine-based diamines with C2-symmetry 2, 3 and their related compounds 4 - 8 were designed and synthesized in optically pure forms. Both (+)- and (-)-2 were prepared from optical active ditosylate 9. 3 was prepared from 3,5-dimethylbenzaldehyde through optical resolution and its absolute stereochemistry was correlated with 2,3-dimethylsuccinate 27. 4 was prepared from (-)-diol 28. 5 - 8 were prepared from 9 and 11.
• 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：——