1,1-Bis(phenylselanyl)propan-2-one | 171005-00-8

• 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: 1,1-Bis(phenylselanyl)propan-2-one
• CAS: 171005-00-8
• 化学式: C₁₅H₁₄OSe₂
• 分子量: 368.196
• InChiKey: NZSSNBZCXJBLLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-Bis(phenylselanyl)propan-2-one 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 1-(phenylselanyl)propan-2-one 、 1,3-bis(phenylseleno)propanone
  参考文献：
  名称：

  Allylation and benzylation of enolates derived from β-phenylselanyl silyl enol ethers

  摘要：

  alpha-Phenylselanyl gamma-unsaturated ketones were obtained through allylation of enolates generated by potassium t-butoxide cleavage of beta-phenylselanyl silyl enol ethers derived from alpha-phenylselanyl ketones. With enoxysilanes prepared from alpha-phenylselanyl aldehydes, O-allylation and O-benzylation of the corresponding enolates were also observed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00296-2
• 作为产物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 、 1-(phenylselanyl)propan-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以56%的产率得到1,1-Bis(phenylselanyl)propan-2-one
  参考文献：
  名称：

  Preparation of α,α-bis(phenylseleno)ketones

  摘要：

  alpha,alpha-Bis(phenylseleno)ketones have been synthesized by phenylselenenylation of enolates derived from alpha-phenylseleno ketones. Depending on the structure of the ketones, three experimental procedures were adopted.

  DOI：

  10.1016/0040-4039(95)01290-x

文献信息

• Some novel routes to 1-hetero-substituted 1-vinylcyclopropanes
  作者：Richard T. Lewis、William B. Motherwell

  DOI：10.1016/s0040-4020(01)92235-5

  日期：1992.2

  carbonyl compounds and diethyl diazomethylphosphonate, can be efficiently trapped by alkenes to give alkylidene-cyclopropane adducts which undergo either [1,3] allyl selenide rearrangement or oxidative selenoxide [2,3] sigmatropic rearrangement to produce 1-phenylseleno- or 1-hydroxy-1-vinylcyclopropanes respectively.

  由碱诱导的α-苯基硒代羰基化合物与二乙基重氮甲基膦酸酯的碱诱导缩合原位生成的3-苯基硒烯-1-烯基苯甲酸酯可被烯烃有效地捕获，从而生成亚烷基-环丙烷加合物，该加合物会经历[1,3]烯丙基亚硒酸酯重排或氧化亚硒酸酯[2,3]σ重排，分别产生1-苯基硒基或1-羟基-1-乙烯基环丙烷。
• Cross-aldol reaction between benzaldehyde and β-phenylselanyl enoxysilanes derived from phenylselanylmethylketones
  作者：Sylvain Ponthieux、Francis Outurquin、Claude Paulmier

  DOI：10.1016/s0040-4039(98)00679-0

  日期：1998.6

  The BF3-mediated aldol reaction between benzaldehyde and beta-phenylselanyl enoxysilanes 1 derived from alpha-phenylselanylmethylketones has led to syn aldols 2 and alpha,alpha-bis(phenylselanyl) ketones 3 as by-products. Using tetrabutylammonium fluoride, the syn and anti aldols 2a were formed from 1a. Syn, syn-2-phenylselanyl 1,3-diols 5a and 5d were obtained by borane reduction of aldols 2a and 2d respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Preparation of α,α-bis(phenylseleno)ketones
  作者：Sylvain Ponthieux、Francis Outurquin、Claude Paulmier

  DOI：10.1016/0040-4039(95)01290-x

  日期：1995.9

  alpha,alpha-Bis(phenylseleno)ketones have been synthesized by phenylselenenylation of enolates derived from alpha-phenylseleno ketones. Depending on the structure of the ketones, three experimental procedures were adopted.
• Allylation and benzylation of enolates derived from β-phenylselanyl silyl enol ethers
  作者：Sylvain Ponthieux、Francis Outurquin、Claude Paulmier

  DOI：10.1016/s0040-4020(97)00296-2

  日期：1997.5

  alpha-Phenylselanyl gamma-unsaturated ketones were obtained through allylation of enolates generated by potassium t-butoxide cleavage of beta-phenylselanyl silyl enol ethers derived from alpha-phenylselanyl ketones. With enoxysilanes prepared from alpha-phenylselanyl aldehydes, O-allylation and O-benzylation of the corresponding enolates were also observed. (C) 1997 Elsevier Science Ltd.