ethyl 2-chloro-2-phenylselanylpropanoate | 185749-71-7

• 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 2-chloro-2-phenylselanylpropanoate
• 英文别名: ethyl α-chloro-α-phenylseleno propionate；α-chloro-α-phenylselenoethyl propionate
• CAS: 185749-71-7
• 化学式: C₁₁H₁₃ClO₂Se
• 分子量: 291.636
• InChiKey: YTVUIOATACTYLS-UHFFFAOYSA-N

物化性质

• 沸点：
  324.1±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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 2-chloro-2-phenylselanylpropanoate 在 间氯过氧苯甲酸 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 2-[2-Oxo-3,4-dihydro-2H-naphthalen-(1Z)-ylidene]-propionic acid ethyl ester
  参考文献：
  名称：

  α-氯代-α-苯基硒酸酯与甲硅烷基烯醇醚的反应。α-苯基硒基-γ-酮酯和γ-丁内酯的合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(96)02151-x
• 作为产物：
  描述：

  ethyl 2-(phenylselanyl)propanoate 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 alpha-氯丙烯酸乙酯 、 ethyl 2-chloro-2-phenylselanylpropanoate
  参考文献：
  名称：

  Synthesis and Reactivity of α- and β-Chloro-α-phenylselanyl Esters

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(00)00648-7

文献信息

• 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。
• A new approach to (±)-heritonin. The preparation of β-tetralones from allylsilanes and acid chlorides
  作者：Claudio C. Silveira、Alessandra Machado、Antonio L. Braga、Eder João Lenardão

  DOI：10.1016/j.tetlet.2004.03.154

  日期：2004.5

  A new method for the preparation of 4-alkyl-β-tetralones is described, by reaction of arylacetic acid chlorides with allylsilanes. Employing β-tetralone 5, the synthesis of (±)-heritonine and (±)-epi-heritonine, natural piscicides isolated from Heritiera littoralis, was achieved in four steps and 22% overall yield. The key step of this synthesis involved the selenocarbenium ion-mediated elaboration

  描述了一种通过芳基酰氯与烯丙基硅烷反应制备4-烷基-β-四氢萘酮的新方法。采用β四氢萘酮5，（±）-heritonine和（±）的合成-外延-heritonine，分离自天然杀鱼银叶树，在四个步骤和22％达到总产率。该合成的关键步骤涉及硒代碳鎓离子介导的天然产物丁烯内酯环的修饰。
• 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.
• 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。