meso-2,3-diphenylsuccinic acid dimethyl ester | 25169-81-7

• 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: meso-2,3-diphenylsuccinic acid dimethyl ester
• 英文别名: meso-2.3-diphenyl-succinic acid dimethyl ester；meso-2.3-Diphenyl-bernsteinsaeure-dimethylester；meso-α,α'-Diphenylsuccindimethylester；d,l-α,α'-Diphenylsuccindimethylester；meso-2,3-Diphenyl-bernsteinsaeure-dimethylester；meso-2,3-Diphenylbernsteinsaeure-dimethylester；dimethyl (2S,3R)-2,3-diphenylbutanedioate
• CAS: 25169-81-7
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: JFIQBXWLKNJROM-IYBDPMFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-2,3-diphenylsuccinic acid dimethyl ester 在 硫酸 作用下， 生成 2,3-diphenylbutanedioate
  参考文献：
  名称：

  Ketene Acetals. XVI. Phenylketene Diethyl- and Dimethylacetals from the Pyrolysis of the Corresponding Orthoesters

  摘要：

  DOI：

  10.1021/ja01214a014
• 作为产物：
  描述：

  1,3-diphenyl-1-propyne 在 aluminum oxide 作用下， 生成 meso-2,3-diphenylsuccinic acid dimethyl ester
  参考文献：
  名称：

  Staab,H.A.; Kurmeier,H.-A., Chemische Berichte, 1968, vol. 101, # 8, p. 2697 - 2708

  摘要：

  DOI：

文献信息

• <i>syn</i>/<i>anti</i>Switching by Specific Heteroatom-Titanium Coordination in the Mannich-Like Synthesis of 2,3-Diaryl-β-amino Acid Derivatives
  作者：Andrea Bonetti、Francesca Clerici、Francesca Foschi、Donatella Nava、Sara Pellegrino、Michele Penso、Raffaella Soave、Maria Luisa Gelmi

  DOI：10.1002/ejoc.201400142

  日期：2014.5

  A very efficient synthesis of 2,3-diaryl-β-amino acid derivatives is realized by a TiCl4/triethylamine-catalyzed Mannich-like reaction of arylacetic or arylthioacetic esters with arylimines. The presence on the arylacetic moiety of an ortho-heteroatom group able to coordinate to the titanium center is of dramatic importance for the outcome of the reaction and to tune the syn/anti diastereoselection

  2,3-二芳基-β-氨基酸衍生物的非常有效的合成是通过芳基乙酸酯或芳基硫代乙酸酯与芳基亚胺的TiCl4/三乙胺催化的曼尼希样反应实现的。能够与钛中心配位的邻杂原子基团的芳基乙酸部分的存在对于反应结果和调节顺/反非对映选择具有重要意义。特别是，对于 oF-、o-Cl- 和 o-Br-芳基乙酸酯，顺式加合物作为主要流行的异构体被分离出来。当使用（-）-8-苯基薄荷酯（2-氟苯基）乙酸酯时，与亚胺的缩合导致高非对映选择性和对映选择性。与立体化学结果和核磁共振研究一致，提出了一个可能的反应机理。
• Dependence of the Reactivities of Titanium Enolates on How They Are Generated:  Diastereoselective Coupling of Phenylacetic Acid Esters Using Titanium Tetrachloride
  作者：Yoshihiro Matsumura、Maiko Nishimura、Hiroyuki Hiu、Mitsuaki Watanabe、Naoki Kise

  DOI：10.1021/jo952204h

  日期：1996.1.1

  phenylacetic acid esters was easily achieved by treating the esters with TiCl(4) and then adding Et(3)N to the resulting solution. The products consisted of dl- and meso-2,3-diphenylsuccinic acid esters with the Claisen condensation product, and the ratio of these products depended on the reaction conditions. Reaction conditions suitable for high dl selectivity were determined, and a dimer of titanium enolate

  通过用TiCl（4）处理酯，然后将Et（3）N添加到所得溶液中，可以轻松实现苯乙酸酯的氧化偶联。产物由dl-和meso-2,3-二苯基丁二酸酯与Claisen缩合产物组成，这些产物的比例取决于反应条件。确定适合于高dl选择性的反应条件，并假定烯醇钛的二聚体作为负责高dl选择性的中间体。将选择性与已知的氧化偶合中的选择性进行比较，在已知的氧化偶合中，烯醇钛中间体是通过烯醇锂和甲硅烷基烯醇醚制备的。结果表明，烯醇钛中间体的反应性取决于其生成方式。
• Reactions of Dimethylaniline with Some Resonance-stabilized Radicals
  作者：Renji Okazaki、Naoki Inamoto

  DOI：10.1246/bcsj.41.1711

  日期：1968.7

  Reactions of dimethylaniline with some resonance-stabilized radicals were studied. 2-Cyano-2-propyl radicals and 2-methoxycarbonyl-2-propyl radicals reacted to give N-methyl-N-(3,4-dicyano-3,4-dimethylpentyl) aniline and the corresponding 3,4-dimethoxycarbonyl derivative, respectively, while benzyl radicals and α-methoxycarbonylbenzyl radicals did not give reaction products with dimethylaniline. Mechanism

  研究了二甲基苯胺与一些共振稳定自由基的反应。2-氰基-2-丙基自由基和2-甲氧基羰基-2-丙基自由基反应得到N-甲基-N-(3,4-二氰基-3,4-二甲基戊基)苯胺和相应的3,4-二甲氧基羰基衍生物，分别，而苄基自由基和α-甲氧基羰基苄基自由基与二甲基苯胺不产生反应产物。提出了这些反应的机理，并指出从二甲基苯胺到自由基的电子转移是这些反应中的一个重要阶段。
• Photochemical Reaction of Diphenylcyclobutenedione Derivatives. Formation and Reaction of Conjugated Bisketene and Its<i>N</i>-Analog
  作者：Naruyoshi Obata、Takeo Takizawa

  DOI：10.1246/bcsj.50.2017

  日期：1977.8

  The photolysis of diphenylcyclobutenedione derivatives (Va, b) under N2 and that in the presence of substrate, O2 or isocyanide, have been studied. The former resulted in the recovery of a large amount of V and the fragmentation; the latter gave the insertion products into V, diphenylmaleic anhydrides and iminocyclopentenones in good yield. The intermediates, bisketene and ketene-ketenimine as primary

  已经研究了二苯基环丁烯二酮衍生物 (Va, b) 在 N2 和底物 O2 或异氰化物存在下的光解。前者导致大量V的回收和碎片化；后者以良好的产率将插入产物转化为 V、二苯基马来酸酐和亚氨基环戊烯酮。中间体，双烯酮和乙烯酮-烯酮亚胺作为初级光产物通过 Va 在甲醇中的光解得到琥珀酸酯和低温红外技术证实。讨论了双烯酮中间体的结构方面。
• Electrochemical ring-opening carboxylation of cyclic carbonate with carbon dioxide
  作者：Li Tao、He Wang、Xiao-Fei Liu、Wei-Min Ren、Xiao-Bing Lu、Wen-Zhen Zhang

  DOI：10.1039/d4cc01695e

  日期：——

  ring-opening carboxylation of styrene carbonates with CO2 to achieve dicarboxylic acids and/or β-hydroxy acids has been developed via the selective cleavage of the C(sp3)–O bond in cyclic carbonates. The product selectivity is probably determined by the stability and reactivity of the key benzylic radical and carbanion intermediate.

  通过选择性裂解环状碳酸酯中的 C(sp 3 )–O 键，开发了苯乙烯碳酸酯与 CO 2的电还原开环羧化以获得二羧酸和/或β-羟基酸。产物选择性可能由关键的苄基和碳负离子中间体的稳定性和反应性决定。