(Z)-4-(phenylselenomethylene)butan-4-olide | 134031-01-9

• 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: (Z)-4-(phenylselenomethylene)butan-4-olide
• 英文别名: 4-(1-phenylselenomethylene)butan-4-olide；5-(phenylselanylmethylidene)oxolan-2-one
• CAS: 134031-01-9
• 化学式: C₁₁H₁₀O₂Se
• 分子量: 253.159
• InChiKey: SKQTZSYDUXSMHX-UHFFFAOYSA-N

物化性质

• 沸点：
  362.7±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (Z)-4-(phenylselenomethylene)butan-4-olide 在 potassium carbonate 作用下， 生成 methyl 4-oxo-5-phenylselenopentanoate
  参考文献：
  名称：

  的alkynoic羧酸与Selenolactonization Ñ -phenylselenophthalimide：乙烯基硒的新颖异构化反应

  摘要：

  硒酸内酯化对于六-4-炔酸和七-4-炔酸（1a）和（1b）具有立体选择性和区域特异性，但是五-4-炔酸（1c）产生立体异构体的混合物。

  DOI：

  10.1039/c39850001082
• 作为产物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 在 N-(苯硒基)邻苯二甲酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 212.0h， 生成 (Z)-4-(phenylselenomethylene)butan-4-olide
  参考文献：
  名称：

  Toru, Takeshi; Fujita, Satoshi; Saito, Makoto, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1999 - 2004

  摘要：

  DOI：

文献信息

• Selenolactonization of alkynoic acids with N-phenylselenophthalimide: novel isomerization reaction of a vinyl selenide
  作者：Takeshi Toru、Satoshi Fujita、Etur� Maekawa

  DOI：10.1039/c39850001082

  日期：——

  Selenolactonization is stereoselective and regiospecific for hex-4-ynoic and hept-4-ynoic acids (1a) and (1b), but pent-4-ynoic acid (1c) gives a mixture of stereoisomers.

  硒酸内酯化对于六-4-炔酸和七-4-炔酸（1a）和（1b）具有立体选择性和区域特异性，但是五-4-炔酸（1c）产生立体异构体的混合物。
• Formation and electrophilic reactions of benzeneselenenyl p-toluenesulfonate. Preparation and properties of addition products with acetylenes
  作者：Thomas G. Back、K. Raman Muralidharan

  DOI：10.1021/jo00008a039

  日期：1991.4

  Benzeneselenenyl p-toluenesulfonate (1) was generated in situ by the reaction of silver p-toluenesulfonate with benzeneselenenyl chloride in acetonitrile. The reagent reacted with acetylenes by electrophilic 1,2-addition to afford the beta-(phenylseleno)vinyl p-toluenesulfonates 2-12, generally in high yield. The latter were formed preferentially by anti addition, but with poor regioselectivity, unless a strongly orienting group (e.g., phenyl) was present. Selenenyl sulfonate 1 was also unexpectedly produced via radical pathways by heating p-toluenesulfonic acid with AIBN in the presence of diphenyl diselenide, or from the pyrolysis of sulfinyl sulfone 15 with the diselenide. The regioisomeric adducts 3 and 4 were prepared from 1 and 1-decyne, and both underwent elimination with potassium tert-butoxide to afford the acetylenic selenide 19 initially, which isomerized to a 6:1 mixture of the propargylic and allenic selenides 20 and 21 upon further equilibration. A Fritsch-Buttenberg-Wiechell rearrangement is proposed for the elimination of 4. The syn elimination of the selenoxide of 4 required forcing conditions and afforded only ca. 20% of the corresponding allenic sulfonate 22. The electrophile 1 induced the efficient cyclization of 5-hexen-1-ol and 4-pentenoic acid to the corresponding pyran 24 and lactone 25, respectively. It failed to cyclize alkynols, but afforded the lactones 28 and 29 from 4-pentynoic acid in low yield.
• Toru, Takeshi; Fujita, Satoshi; Saito, Makoto, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1999 - 2004
  作者：Toru, Takeshi、Fujita, Satoshi、Saito, Makoto、Maekawa, Eturo

  DOI：——

  日期：——