ethyl-α,α-bis(phenylseleno) acetate | 72041-41-9

• 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: ethyl-α,α-bis(phenylseleno) acetate
• 英文别名: α,α-Bisphenylseleno ethyl acetate；Ethyl 2,2-di(phenylselanyl)acetate；ethyl bis(phenylselanyl)acetate；Acetic acid, bis(phenylseleno)-, ethyl ester；ethyl 2,2-bis(phenylselanyl)acetate
• CAS: 72041-41-9
• 化学式: C₁₆H₁₆O₂Se₂
• 分子量: 398.222
• InChiKey: SKGOWPNUHUDTMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl-α,α-bis(phenylseleno) acetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以70%的产率得到乙酸,溴(苯基硒代)-,乙基酯
  参考文献：
  名称：

  A Convenient Synthesis of Arylselenoacetals and α-Halo-α-(phenylseleno)alkanes

  摘要：

  alpha-Halo-alpha-(phenylseleno)alkanes are prepared by treatment of selenoacetals with halogenating agents. Selenoacetals are produced by heating alpha-halo-alpha-(phenylseleno)alkanes on neutral alumina

  DOI：

  10.1080/00397919508010797
• 作为产物：
  描述：

  二苯基二硒醚 在 sodium tetrahydroborate 、 三甲基氯硅烷 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 硝基甲烷 、 乙醇 为溶剂， 反应 1.25h， 生成 ethyl-α,α-bis(phenylseleno) acetate
  参考文献：
  名称：

  alpha催化的碳-碳键的形成，使用α-有机硫烷基和有机纤维基-α-氟乙酸衍生物。

  摘要：

  soft催化的α-有机硫烷基和有机糖基-α-氟乙酸酯1-2，乙酰胺3-4和乙腈5与柔软的亲核试剂的反应进行，得到的产物6a-b，7a-c，8a-c，9a-e好到高产。我们还成功地进行了dium催化的分子内环化反应，并获得了独特的5-亚甲基-2-氧代四氢吡喃16-17。

  DOI：

  10.1248/cpb.54.1611

文献信息

• Preparation and Oxidation of α-Phenylselanyl Esters
  作者：Loic Lebarillier、Francis Outurquin、Claude Paulmier

  DOI：10.1016/s0040-4020(00)00647-5

  日期：2000.9

  and selenenylation of selenium-stabilized ester enolates have allowed the preparation of α-phenylselanyl esters 5, 7, 8 and of α,α-bis(phenylselanyl)esters 6, respectively. The competitive selenophilic reaction, leading to an allylic phenylselenide 9, was avoided in the presence of HMPA. α-phenylselanyl α,β-unsaturated esters 15 were prepared by oxidation of compounds 6 and dehydrohalogenation of β-chloroesters

  烷基化和硒稳定酯烯醇化物的selenenylation已经允许α-phenylselanyl酯的制备5，7，8 α的和，α -双（phenylselanyl）酯6分别。在HMPA存在下，避免了竞争性的亲脂性反应，导致烯丙基苯基硒化物9。通过化合物6的氧化和β-氯代酯17的脱卤化氢制备α-苯基硒基α，β-不饱和酯15。还研究了其他一些转化：氧化，酯交换和格氏反应。Z酯的H 2 O 2氧化15导致产生稳定的E -α-硒烯酸酯20。
• Friedel-crafts reaction of α-(phenylseleno)carboethoxy methyl compounds
  作者：C.C. Silveira、E.J. Lenardão、J.V. Comasseto、M.J. Dabdoub

  DOI：10.1016/s0040-4039(00)93544-5

  日期：1991.10

  α-Bromo,α-phenylseleno ethyl acetate and α,α-bisphenylseleno ethyl acetate react with aromatic hydrocarbons under Friedel-Crafts conditions to give α-aryl, α-phenylseleno ethyl acetates, which by reduction with thienylditelluride (catalytic) and sodium borohydride led to the corresponding aryl acetic acids.

  在Friedel-Crafts条件下，α-溴，α-苯基硒代乙酸乙酯和α，α-双苯基硒代乙酸乙酯与芳烃反应生成α-芳基，α-苯基硒代乙酸乙酯，并通过噻吩二碲化物（催化）和硼氢化钠还原生成相应的芳基乙酸。
• 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。
• Synthesis of α-phenylchalcogeno acetic acids, ethyl-α-phenylchalcogeno acetates and ethyl-α-halo-α-phenylchalcogeno acetates
  作者：M Dabdoub

  DOI：10.1016/0022-328x(93)80355-f

  日期：1993.11.2

  Reaction of phenyltellurolate or phenylselenolate anion with alpha-bromoacetic acid under phase transfer conditions using a liquid-solid system affords the alpha-phenyltelluro acetic acid and the alpha-phenylseleno acetic acid in 44 and 50% yields respectively. Under similar reaction conditions, phenyl chalcogenate anions react with ethyl alpha-bromoacetate to give the corresponding ethyl-alpha-phenyltelluro acetate in 52% and ethyl-alpha-phenylseleno acetate in 47% yield.Reaction of phenylselenenyl chloride with ethyl diazoacetate in THF at 0-degrees-C yields exclusively the ethyl-alpha-chloro-alpha-phenylseleno acetate in 88% yield. Similar reactions performed by addition of phenylselenenyl bromide in THF or benzene to the ethyl diazoacetate at different temperatures result in mixtures of ethyl-alpha-bromo-alpha-phenylseleno acetate and ethyl-alpha,alpha-bis(phenylseleno) acetate in different ratios. However, when the ethyl diazoacetate was slowly added to a solution of phenylselenenyl bromide in benzene under reflux, the ethyl-alpha-bromo-alpha-phenylseleno acetate was obtained in 84% yield as the only product. Reaction of ethyl diazoacetate with phenyltellurenyl bromide in benzene at room temperature results in formation of ethyl-alpha-bromo-alpha-phenyltelluro acetate that decomposes rapidly into the corresponding tellurone.Addition of ethyl diazoacetate to a mixture of diphenyldiselenide and copper sulfate in benzene under reflux results in a mixture of ethyl-alpha-phenylseleno acetate: ethyl-alpha,alpha-bis(phenylseleno) acetate (10:1). Using an alternative route, the ethyl-alpha-phenylseleno acetate was obtained in 74% yield by esterification of alpha-phenylseleno acetic acid in benzene with ethanol/sulfuric acid. The ethyl-alpha-phenylseleno acetate was transformed into the ethyl-alpha-bromo-alpha-phenylseleno acetate in 41% yield by treatment with N-bromosuccinimide.On the other hand, the copper-catalyzed thermal reaction of ethyl diazoacetate with diphenyl ditelluride in benzene afforded the corresponding ethyl-alpha-phenyltelluro acetate as the only product.
• Curini; Epifano; Marcotullio, Synlett, 2000, # 12, p. 1813 - 1815
  作者：Curini、Epifano、Marcotullio、Rosati

  DOI：——

  日期：——