meso-3,4-diphenyladipic acid dimethyl ester | 7028-47-9

• 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: meso-3,4-diphenyladipic acid dimethyl ester
• 英文别名: methyl diphenyladipate；meso-diphenyl-2,3-adipate de methyle；dl-diphenyl-2,3-adipate de methyl；Rac-Dimethyl-3,4-diphenyladipiat；(R,R+S,S)-Dimethyl-3,4-dipenyladipat；dimethyl 3,4-diphenylhexanedioate
• CAS: 7028-47-9
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: WPIVKXXHMIRCBT-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 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：

  meso-3,4-diphenyladipic acid dimethyl ester 在 硫酸 、 potassium carbonate 作用下， 生成 meso-3,4-diphenyl-adipic acid dimethyl ester
  参考文献：
  名称：

  Henle, Justus Liebigs Annalen der Chemie, 1906, vol. 348, p. 29

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl cinnamate 在 三氢化钐 、 碘 、 氢化铝 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以60%的产率得到meso-3,4-diphenyladipic acid dimethyl ester
  参考文献：
  名称：

  Samarium-induced reductive dimerization of methyl cinnamate: synthesis of 2,8-diamino chrysene

  摘要：

  Samarium metal-induced reductive dimerization of methyl cinnamate was performed for the first time. A unique role for aluminum was indicated in the dimerization reaction. The intermediate adipate ester was converted to 2,8-diamino chrysene. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.087

文献信息

• Convenient synthesis of a reactive ester homoenolate
  作者：Erin DiMauro、Albert J. Fry

  DOI：10.1016/s0040-4039(99)01653-6

  日期：1999.11

  Reaction between methyl 3-phenyl-3-trimethylsilylpropionate (8) and catalytic quantities of tetrabutylammonium triphenyldifluorosilicate (TBAT) effects desilylation to the corresponding homoenolate, which can be trapped by a variety of electrophiles. Rearrangement of the homoenolate to the more stable enolate was not observed. The reaction amounted to overall umpolung of methyl cinnamate, the α,β-unsaturated

  3-苯基-3-三甲基甲硅烷基丙酸甲酯（8）与催化量的三苯基二氟硅酸四丁基铵（TBAT）之间的反应会导致甲硅烷基化为相应的均烯酸酯，该均烯酸酯会被各种亲电试剂捕获。没有观察到均烯酸酯重排至更稳定的烯酸酯。该反应总计为肉桂酸甲酯的整体，这是α，β-不饱和酯，由其制备了8。
• Photoinduced electron transfer reactions of cyclopropanone acetal with conjugated enones in the presence of a redox-type photosensitizer
  作者：Manabu Abe、Masatomo Nojima、Akira Oku

  DOI：10.1016/0040-4039(96)00155-4

  日期：1996.3

  Photoreactions of the cyclopropanone acetal 1 with conjugated enones 2 in the presence of phenanthrene or pyrene as a redox-type photosensitizer gave the corresponding cross-coupling product 3 or mixtures of 3 with 5 in good yields together with the β-carbonyl radical-dimer 4.

  在菲或pyr作为氧化还原型光敏剂的存在下，环丙烷丙酮缩醛1与共轭烯酮2的光反应可得到相应的交叉偶联产物3或3与5的混合物，以及高产率的β-羰基自由基二聚体4。
• Hydroxylated HMPA Enhances both Reduction Potential and Proton Donation in SmI₂ Reactions
  作者：Sandipan Halder、Shmaryahu Hoz

  DOI：10.1021/jo500161s

  日期：2014.3.21

  of the methyl groups was substituted by a CH2CH2OH unit was synthesized. Cyclic voltammetry studies have shown that it resembles HMPA in its ability to enhance the reduction potential of SmI2, and reactivity studies show that it has also efficient proton shift capabilities. The various aspects of this additive were examined in the reactions of SmI2 with three substrates: benzyl chloride, methyl cinnamate

  已知HMPA会增加SmI 2的还原电位。然而，在许多情况下，转移的电子从衬底的自由基阴离子返回到Sm 3+。这可以通过有效捕获自由基阴离子来避免：例如通过质子化。但是，质子供体从本体中获得的双分子质子化可能太慢而无法与反向电子转移过程竞争。通过使用与SmI 2络合的质子供体，可以实现有效的单分子质子化，在这种情况下，质子在离子对中单分子转移。HMPA的衍生物，其中一个甲基被CH 2 CH 2取代合成了OH单元。循环伏安法研究表明，它在增强SmI 2还原潜力方面类似于HMPA ，反应性研究表明，它也具有高效的质子转移能力。在SmI 2与三种底物：苄基氯，肉桂酸甲酯和蒽的反应中检查了该添加剂的各个方面。
• Hydropyridylation of α,β-Unsaturated Esters through Electroreduction of 4-Cyanopyridine
  作者：Hua-Jian Zhou、Jing-Mei Huang

  DOI：10.1021/acs.joc.2c00177

  日期：2022.4.15

  A mild and highly efficient method for the hydropyridylation of α,β-unsaturated esters has been developed. This protocol provides the products smoothly with a wide substrate scope in an undivided cell under ambient conditions. Moreover, studies showed that the scope could be extended to other unsaturated compounds, including enones and aldehydes.

  开发了一种温和高效的α,β-不饱和酯加氢吡啶化方法。该协议在环境条件下在未分裂的细胞中顺利地为产品提供了广泛的底物范围。此外，研究表明范围可以扩展到其他不饱和化合物，包括烯酮和醛。
• N-Heterocyclic Carbene Catalyzed Cross Dehydrogenative Coupling of Aldehydes with Methanol: Combined Use of Eosin Y and Hexachloroethane
  作者：Hideto Miyabe、Eito Yoshioka、Hiroki Takahashi、Akane Kubo、Miki Ohno、Fuuka Watanabe、Rino Shiono、Yuuki Miyazaki

  DOI：10.1055/a-1918-4406

  日期：2022.12

  Cross dehydrogenative coupling of aldehydes with methanol was investigated under organocatalytic conditions based on the cooperation­ between N-heterocyclic carbene and eosin Y·Na as an organophotocatalys­t. The combined use of eosin Y·Na and hexachloro­ethane (C2Cl6) was the effective method for the oxidative esterification of various aldehydes, because the oxidation steps are promoted by two pathways

  基于N-杂环卡宾与曙红Y·Na作为有机光催化剂的协同作用，在有机催化条件下研究了醛与甲醇的交叉脱氢偶联。曙红Y·Na和六氯乙烷（C 2 Cl 6）的联合使用是各种醛氧化酯化的有效方法，因为氧化步骤由与活化光催化剂和C 2 Cl 6相关的两条途径促进。相比之下，曙红 Y·Na 和溴三氯甲烷 (BrCCl 3 ) 的联合使用仅对简单的肉桂醛衍生物的氧化酯化有效，其中 BrCCl 3促进作为溴化试剂向自由基中间体的氧化。