ethyl α-chloro-α-phenylseleno acetate | 142753-40-0

• 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: ethyl α-chloro-α-phenylseleno acetate
• 英文别名: ethyl chloro(phenylselanyl)acetate；Ethyl 2-chloro-2-phenylselanylacetate
• CAS: 142753-40-0
• 化学式: C₁₀H₁₁ClO₂Se
• 分子量: 277.609
• InChiKey: QAMLLXJSCPUNAD-UHFFFAOYSA-N

物化性质

• 沸点：
  314.7±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 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：

  ethyl α-chloro-α-phenylseleno acetate 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 以65%的产率得到Chloro-fluoro-phenylselanyl-acetic acid ethyl ester
  参考文献：
  名称：

  有机化合物的电解部分氟化。3.有机硒化合物的区域选择性阳极单氟化及其合成应用

  摘要：

  带有氰基，酯和酰胺基等吸电子基团的硒的区域选择性阳极α-单氟化已成功进行。通过使用制备的α-氟代α-氟代硒酸酯，可以实现α-氟代α-氟代α，β-不饱和酯的高度立体选择性合成。

  DOI：

  10.1016/s0040-4039(00)79840-6
• 作为产物：
  描述：

  ethyl 2-fluoro-2-(phenylselanyl)acetate 在 三甲基氯硅烷 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 硝基甲烷 为溶剂， 反应 0.08h， 以100%的产率得到ethyl α-chloro-α-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

• Reaction of Ethyl α-Chloro-α-phenylselenoacetate with Alkenes: Synthesis of α-Phenylseleno-γ-Butyrolactones
  作者：Claudio C. Silveira、Marcelo A. Araujo、Eder J. Lenardão、Antonio L. Braga、Miguel J. Dabdoub

  DOI：10.1055/s-1995-4101

  日期：1995.10

  Ethyl α-chloro-α-phenylselenoacetate (1) reacts with alk-1-enes in the presence of TiCl4 to give the corresponding α-phenylseleno γ,δ-unsaturated esters. Reaction of 1 with di- and trisubstituted alkenes and SnCl4 as a Lewis acid affords γ-butyrolactones directly and a minor amount of the γ,δ-unsaturated esters. These esters were converted into γ-butyrolactones on hydrolysis and reaction with electrophiles.

  乙基α-氯-α-苯硒基乙酸酯（1）在TiCl4存在下与烷-1-烯反应，生成相应的α-苯硒基γ,δ-不饱和酯。1与二取代和三取代烯烃以及路易斯酸SnCl4反应，直接得到γ-丁内酯，以及少量γ,δ-不饱和酯。这些酯在水分解和亲电试剂反应下转化为γ-丁内酯。
• Reaction of α-chloro-α-phenylselenoesters with silyl enol ethers. Synthesis of α-phenylseleno-γ-keto esters and γ-butyrolactones
  作者：Claudio C. Silveira、Antonio L. Braga、Alessandra Machado、Gustavo L. Fiorin、Miguel J Dabdoub

  DOI：10.1016/s0040-4039(96)02151-x

  日期：1996.12

  Silyl enol ethers of ketones are alkylated with ethyl α-chloro-α-phenylseleno acetate 1a or with ethyl α-chloro-α-phenylseleno propionate 1b, mediated by zinc bromide to give the corresponding α-phenylseleno-γ-keto esters 3 in moderate to good yields.

  将酮的甲硅烷基烯醇醚用α-氯-α-苯基硒代乙酸乙酯1a或α-氯-α-苯基硒代丙酸乙酯1b烷基化，并由溴化锌介导，得到适量的相应α-苯基硒代-γ-酮酸酯3高产。
• Pictet-Spengler condensation of N-sulfonyl-β-phenethylamines with α-chloro-α-phenylselenoesters. New synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylates
  作者：Claudio C. Silveira、Carmem R. Bernardi、Antonio L. Braga、Teodoro S. Kaufman

  DOI：10.1016/s0040-4039(99)00958-2

  日期：1999.7

  The reaction of N-sulfonyl-β-phenethylamines with α-chloro-α-phenylseleno acetate/propionate esters under Lewis acid promotion gives moderate to good yields of the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylates. Varying degrees of diastereoselection were obtained using chiral sulfonamides and/or esters. Employing this strategy, the achievement of a new total synthesis of Calycotomine is

  在路易斯酸促进下，N-磺酰基-β-苯乙胺与α-氯-α-苯基硒代乙酸/丙酸酯的反应产生相应的1,2,3,4-四氢异喹啉-1-羧酸酯中等至良好的产率。使用手性磺酰胺和/或酯可得到不同程度的非对映选择性。据报道，采用这种策略，可以实现新的全合成卡托乙胺的合成。
• 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.
• Synthesis and Reactivity of α- and β-Chloro-α-phenylselanyl Esters
  作者：Loic Lebarillier、Francis Outurquin、Claude Paulmier

  DOI：10.1016/s0040-4020(00)00648-7

  日期：2000.9

  Thermal decomposition of the dichloro-adducts derived from alpha-phenylselanylesters 1, 2 and 4 has been studied. N-Chloro-succinimide treatment of esters 2 was an efficient preparative method for alpha-chloro-alpha-phenylselanylesters 10 and alpha-chloro-alpha,beta-unsaturated esters 11. Some transformations of esters 10 were achieved. alpha,beta-Dichloro-alpha-phenylselanylesters 22 were prepared from beta-chloro-alpha-phenyl selanylesters 5 or by decomposition of the dichloroselenuranes 21 derived from esters 4. (C) 2000 Elsevier Science Ltd. All rights reserved.