meso-2,3-dimethyl-2,3-diphenylsuccinic acid dimethyl ester | 84892-15-9

• 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-2,3-dimethyl-2,3-diphenylsuccinic acid dimethyl ester
• 英文别名: meso-dimethyl 2,3-dimethyl-2,3-diphenylbutanedioate；DL-dimethyl 2,3-dimethyl-2,3-diphenylbutanedioate；dimethyl (2R,3S)-2,3-dimethyl-2,3-diphenylbutanedioate
• CAS: 84892-15-9；90158-84-2；98475-02-6；84892-14-8
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: IAXJYGLIQXWNDQ-BGYRXZFFSA-N

物化性质

• 沸点：
  415.4±40.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 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

• 作为产物：
  描述：

  Alpha-甲基苯乙酸甲酯 在 mercury dibromide N-溴代丁二酰亚胺(NBS) 、 copper dichloride 、 锌 作用下， 以 四氯化碳 为溶剂， 生成 meso-2,3-dimethyl-2,3-diphenylsuccinic acid dimethyl ester
  参考文献：
  名称：

  Thermal cleavage of the 3,4 bond in a cyclobutane-1,2-dione

  摘要：

  Pyrolysis of trans-3,4-dimethyl-3,4-diphenylcyclobutane-1,2-dione results in an isomerization interpreted to involve formation of a dioxatetramethyleneethane biradical. This biradical would arise from a hitherto unprecedented 3,4 bond cleavage.

  DOI：

  10.1016/s0040-4039(00)73665-3

文献信息

• The synthesis and stereospecific solid-state photodecarbonylation of hexasubstituted meso- and d,l-ketones
  作者：Saori Shiraki、Arunkumar Natarajan、Miguel A. Garcia-Garibay

  DOI：10.1039/c1pp05080j

  日期：2011.9

  Tertiary carbanions were trapped with half an equivalent of diphosgene to give meso- and d,l-hexasubstituted ketones in moderate yields and modest diastereoselectivities. The ketones were also synthesized by a step-wise synthesis in which the carbonyl group was first installed as an acid before activation and the second nucleophilic attack. This second method gave lower yields but similar diastereoselectivites

  第三碳负离子被困了一半的当量 双光气为了让观-和d，升-hexasubstituted中等产量和适度的非对映选择性酮。还通过逐步合成来合成酮，其中在活化和第二次亲核进攻之前首先将羰基作为酸安装。第二种方法收率较低，但非对映选择性相似。还确定了两种方法的立体极限。所得结晶酮的光解产生了溶液中产物的混合物，但在固态下发生了化学选择性和非对映特异性。
• 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。
• Mok, Pearl L. H.; Roberts, Brian P.; McKetty, Paula T., Journal of the Chemical Society. Perkin transactions II, 1993, # 4, p. 665 - 674
  作者：Mok, Pearl L. H.、Roberts, Brian P.、McKetty, Paula T.

  DOI：——

  日期：——
• Luca, Carlo de; Inesi, Achille; Rampazzo, Liliana, Journal of the Chemical Society. Perkin transactions II, 1982, p. 1403 - 1408
  作者：Luca, Carlo de、Inesi, Achille、Rampazzo, Liliana

  DOI：——

  日期：——
• NG, CHI TAT;WANG, XIAOJUN;LUH, TIEN-YAU, J. ORG. CHEM., 53,(1988) N 11, 2536-2539
  作者：NG, CHI TAT、WANG, XIAOJUN、LUH, TIEN-YAU

  DOI：——

  日期：——