Dimethyl 2,2-(diphenylseleno)propanedioate | 72041-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Dimethyl 2,2-(diphenylseleno)propanedioate
• 英文别名: dimethyl 2,2-di(phenylseleno)propanedioate；Dimethyl 2,2-bis(phenylselanyl)propanedioate
• CAS: 72041-42-0
• 化学式: C₁₇H₁₆O₄Se₂
• 分子量: 442.232
• InChiKey: JWDNUNUBLFJNIC-UHFFFAOYSA-N

物化性质

• 沸点：
  494.7±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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 2,2-(diphenylseleno)propanedioate 以 苯 为溶剂， 反应 37.0h， 以86%的产率得到四甲基乙烯四羧酸酯
  参考文献：
  名称：

  The Photolytic Disproportionation of Dialkyl 2,2-Di(Phenylseleno)propanedioates

  摘要：

  Dialkyl-2,2-di(phenylseleno)propanedioates undergo disproportionation to form tetralkyl 1,1,2,2-ethylene tetracarboxylates and diphenyl diselenide upon photolysis. Evidence for the intermediacy of a capto-dative radical intermediate in this process is described.

  DOI：

  10.1080/00397919508010784
• 作为产物：
  描述：

  丙二酸二甲酯 在 sodium hydride 作用下， 生成 Dimethyl 2,2-(diphenylseleno)propanedioate
  参考文献：
  名称：

  Radical addition reactions of 2-(phenylseleno)propanedioates to alkenes and alkynes

  摘要：

  Sunlamp photolysis of methyl or ethyl 2-(phenylseleno)propanedioate with a variety of alkenes and alkynes in benzene yielded addition products in good to excellent yields. The proposed mechanism involves a radical chain process in which addition of a malonate ester radical is followed by phenylseleno transfer. Monosubstituted alkenes,l,l-and l,2-disubstituted alkenes, terminal alkynes, and internal alkynes were shown to undergo this reaction. Addition to diallyl ether led to substituted tetrahydrofurans, characteristic of a process involving initial addition, followed by cyclization prior to phenylseleno transfer. Vinyl arenes, conjugated dienes, and unsaturated carbonyl compounds proved unreactive.

  DOI：

  10.1021/jo00064a023

文献信息

• Catalysed insertion reactions of diphenyl diselenide with ethyl diazoacetate and dimethyl diazomalonate
  作者：Roberto Pellicciari、Massimo Curini、Paolo Ceccherelli、Renata Fringuelli

  DOI：10.1039/c39790000440

  日期：——

  Se–Se Insertion reactions were observed when ethyl diazoacetate and dimethyl diazomalonate were allowed to react with diphenyl diselenide (1) in the presence of catalysts such as copper–bronze or BF3·Et2O.

  当重氮乙酸乙酯和重氮丙二酸二甲酯在铜-青铜或BF 3 ·Et 2 O等催化剂存在下与二苯基二硒化物（1）反应时，观察到Se-Se插入反应。
• Byers Jeffrey H., Thissell Jameson G., Synth. Commun, 25 (1995) N 1, S 21-26
  作者：Byers Jeffrey H., Thissell Jameson G.

  DOI：——

  日期：——
• The Photolytic Disproportionation of Dialkyl 2,2-Di(Phenylseleno)propanedioates
  作者：Jeffrey H. Byers、Jameson G. Thissell

  DOI：10.1080/00397919508010784

  日期：1995.1

  Dialkyl-2,2-di(phenylseleno)propanedioates undergo disproportionation to form tetralkyl 1,1,2,2-ethylene tetracarboxylates and diphenyl diselenide upon photolysis. Evidence for the intermediacy of a capto-dative radical intermediate in this process is described.
• Radical addition reactions of 2-(phenylseleno)propanedioates to alkenes and alkynes
  作者：Jeffrey H. Byers、Gregory C. Lane

  DOI：10.1021/jo00064a023

  日期：1993.6

  Sunlamp photolysis of methyl or ethyl 2-(phenylseleno)propanedioate with a variety of alkenes and alkynes in benzene yielded addition products in good to excellent yields. The proposed mechanism involves a radical chain process in which addition of a malonate ester radical is followed by phenylseleno transfer. Monosubstituted alkenes,l,l-and l,2-disubstituted alkenes, terminal alkynes, and internal alkynes were shown to undergo this reaction. Addition to diallyl ether led to substituted tetrahydrofurans, characteristic of a process involving initial addition, followed by cyclization prior to phenylseleno transfer. Vinyl arenes, conjugated dienes, and unsaturated carbonyl compounds proved unreactive.