乙酸,溴(苯基硒代)-,乙基酯 | 138100-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙酸,溴(苯基硒代)-,乙基酯
• 英文名称: α-Bromo,α-phenylseleno ethyl acetate
• 英文别名: ethyl α-bromo-α-phenylseleno acetate；ethyl-α-bromo-α-phenylseleno acetate；α-bromo-α-phenylseleno acetate；ethyl 2-bromo-2-(phenylselanyl)acetate；Acetic acid, bromo(phenylseleno)-, ethyl ester；ethyl 2-bromo-2-phenylselanylacetate
• CAS: 138100-77-3
• 化学式: C₁₀H₁₁BrO₂Se
• 分子量: 322.06
• InChiKey: MPCDGJXZAOLPSS-UHFFFAOYSA-N

物化性质

• 沸点：
  325.9±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  乙酸,溴(苯基硒代)-,乙基酯 、 烯丙基三甲基硅烷 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 以50%的产率得到ethyl 2-(phenylselanyl)pent-4-enoate
  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
• 作为产物：
  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

文献信息

• 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。
• 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.
• Silveira Claudio C., Perin Gelson, Braga Antonio L., Synth. Commun, 25 (1995) N 1, S 117-126
  作者：Silveira Claudio C., Perin Gelson, Braga Antonio L.

  DOI：——

  日期：——
• A Convenient Synthesis of Arylselenoacetals and α-Halo-α-(phenylseleno)alkanes
  作者：Claudio C. Silveira、Gelson Perin、Antonio L. Braga

  DOI：10.1080/00397919508010797

  日期：1995.1

  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
• Scandium-Catalyzed Carbon-Carbon Bond Formations Using .ALPHA.-Organosulfanyl and Organoselanyl-.ALPHA.-fluoroacetic Acid Derivatives
  作者：Kohei Gotoh、Teruhisa Yamamoto、Mitsuhiro Yoshimatsu

  DOI：10.1248/cpb.54.1611

  日期：——

  The scandium-catalyzed reactions of alpha-organosulfanyl and organoselanyl-alpha-fluoroacetates 1-2, acetamides 3-4 and acetonitrile 5 with soft nucleophiles proceeded to give the products 6a-b, 7a-c, 8a-c, 9a-e in good to high yields. We also successfully performed the scandium-catalyzed intramolecular cyclization reactions and obtained the unique 5-methylene-2-oxotetrahydropyrans 16-17.

  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。