d,l-3,4-Bis-(4-methoxy-phenyl)-adipinsaeure-dimethylester | 97116-47-7

• 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: d,l-3,4-Bis-(4-methoxy-phenyl)-adipinsaeure-dimethylester
• 英文别名: racem.-3.4-bis-(4-methoxy-phenyl)-adipic acid dimethyl ester；racem.-3.4-Bis-(4-methoxy-phenyl)-adipinsaeure-dimethylester；dimethyl (3S,4S)-3,4-bis(4-methoxyphenyl)hexanedioate
• CAS: 97116-47-7
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: IGCAIHLXNHWPFM-WOJBJXKFSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  494.1±45.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  d,l-3,4-Bis-(4-methoxy-phenyl)-adipinsaeure-dimethylester 在 sodium hydroxide 作用下， 生成 meso-3,4-bis-(4-methoxy-phenyl)-adipic acid
  参考文献：
  名称：

  340.合成与甾醇有关的物质的实验。第四部分 ry的某些衍生物（续）

  摘要：

  DOI：

  10.1039/jr9350001412
• 作为产物：
  描述：

  (e)-p-甲氧基肉桂酸甲酯 在 sodium hydroxide 、 三甲基氯硅烷 、 四乙基对甲苯磺酸铵 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 d,l-3,4-Bis-(4-methoxy-phenyl)-adipinsaeure-dimethylester
  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

• The role of M cells in mucosal immunity
  作者：L. J. Hathaway、J.-P. Kraehenbuhl*

  DOI：10.1007/pl00000693

  日期：2000.2

  Mucosa-associated lymphoid tissue in the respiratory and digestive tracts are covered by a specialized epithelium, the follicle-associated epithelium, which includes M cells, which are specialized for the uptake and transcytosis of macromolecules and microorganisms. Following transcytosis, antigens are released to cells of the immune system in lymphoid aggregates beneath the epithelium where antigen processing and presentation and stimulation of specific B and T lymphocytes are achieved. Circulation of the lymphoid cells enables their homing to their original, and other, mucosal sites where they exert the effector function. Such a response may be dominated by secretory immunoglobulin A release and may include cytotoxic T lymphocyte action. Binding of particles to the apical M cell membrane may be nonspecific or due to specific interaction between molecules such as integrins and lectins. Exploiting the specific binding to M cells is an aim for mucosal vaccination, for example to increase the efficiency of uptake of an oral vaccine by its conjugation to an M-cel-specific molecule. Alternatively, an M-cell-specific live vector, such as attenuated Salmonella bacteria, may be used to deliver epitopes of other organisms. Mucosal vaccination efficiency may also be enhanced by a temporary increase in the number of M cells.Therefore, investigation of the properties and ontogeny of M cells must be pursued to allow the development of better mucosal vaccines for the future.
• 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.
• Entschwefelung von 3,4-Di-phenyl-thiophen-Verbindungen mit Raney-Nickel
  作者：O. Dann、G. Hauck

  DOI：10.1002/ardp.19602930211

  日期：——
• 340. Experiments on the synthesis of substances related to the sterols. Part IV. Some derivatives of chrysene (contd.)
  作者：H. J. Lewis、G. R. Ramage、Robert Robinson

  DOI：10.1039/jr9350001412

  日期：——
• New Compounds. cis- and trans-3,4-Bis-(p-methoxyphenyl)-cyclopentanone
  作者：George Mueller、Fleur Bateman

  DOI：10.1021/ja01135a067

  日期：1952.8