dimethyl (3R,4R)-diphenyladipate | 86117-68-2

• 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: dimethyl (3R,4R)-diphenyladipate
• 英文别名: Hexanedioic acid, 3,4-diphenyl-, dimethyl ester, (3R,4R)-；dimethyl (3R,4R)-3,4-diphenylhexanedioate
• CAS: 86117-68-2
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: WPIVKXXHMIRCBT-ROUUACIJSA-N

物化性质

• 沸点：
  431.5±45.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl (3R,4R)-diphenyladipate 、 乙酰氯 、 三氯化铝 以58%的产率得到
  参考文献：
  名称：

  BEROVA, N.;SPASSOV, S.;RAKOVSKA, R., IZV. XIM. BLG. AN, 1982, 15, N 2, 217-227

  摘要：

  DOI：
• 作为产物：
  描述：

  [(1S,2S,3R,4S)-3-benzhydryl-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (E)-3-phenylprop-2-enoate 在 lithium aluminium tetrahydride 、 四乙基对甲苯磺酸铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.5h， 生成 dimethyl (3R,4R)-diphenyladipate
  参考文献：
  名称：

  肉桂酸酯通过电还原的立体选择性加氢偶联：应用于不对称合成加氢二聚体。

  摘要：

  Ar-取代的肉桂酸甲酯在乙腈中的电还原立体选择性地产生了全反式环化的二聚体（58约为90％de）。在所有情况下，也会形成少量（<10％的收率）内消旋二聚体。电解是使用恒定电压的不分隔电池方便地进行的。用半经验方法计算了水耦合的过渡态。全反式环化的二聚体被转化为C（2）对称的dl-3,4-二芳基己二酸和反式3,4-二芳基环戊烷。由（1R）-（+）-樟脑制备的手性辅助[（1R）-exo] -3-exo-（二苯甲基）冰片，对于通过电还原将肉桂酸酯进行立体选择性加氢偶联非常有效。（3R，4R）-3,4-二芳基己二酸酯和（3R，4R）-3,4-二芳基己烷-1

  DOI：

  10.1021/jo026183k

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.
• Stereoselective Hydrocoupling of Optically Active 3-<i>trans</i>-Cinnamoyloxazolidinones by Electroreduction
  作者：Naoki Kise、Syun-ichiro Mashiba、Nasuo Ueda

  DOI：10.1021/jo981231f

  日期：1998.10.1

  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.
• Stereoselective Hydrocoupling of Cinnamic Acid Esters by Electroreduction:  Application to Asymmetric Synthesis of Hydrodimers
  作者：Naoki Kise、Shumei Iitaka、Keisuke Iwasaki、Nasuo Ueda

  DOI：10.1021/jo026183k

  日期：2002.11.1

  The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58 approximately 90% de). In all cases, small amounts (<10% yield) of meso hydrodimers were also formed. The electrolysis was performed conveniently using an undivided cell at a constant current. The transition states for the hydrocoupling were calculated with semiempirical

  Ar-取代的肉桂酸甲酯在乙腈中的电还原立体选择性地产生了全反式环化的二聚体（58约为90％de）。在所有情况下，也会形成少量（<10％的收率）内消旋二聚体。电解是使用恒定电压的不分隔电池方便地进行的。用半经验方法计算了水耦合的过渡态。全反式环化的二聚体被转化为C（2）对称的dl-3,4-二芳基己二酸和反式3,4-二芳基环戊烷。由（1R）-（+）-樟脑制备的手性辅助[（1R）-exo] -3-exo-（二苯甲基）冰片，对于通过电还原将肉桂酸酯进行立体选择性加氢偶联非常有效。（3R，4R）-3,4-二芳基己二酸酯和（3R，4R）-3,4-二芳基己烷-1
• BEROVA, N.;SPASSOV, S.;RAKOVSKA, R., IZV. XIM. BLG. AN, 1982, 15, N 2, 217-227
  作者：BEROVA, N.、SPASSOV, S.、RAKOVSKA, R.

  DOI：——

  日期：——