3,4-epoxy-1,3-diphenyl-1-butanoate | 133957-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-epoxy-1,3-diphenyl-1-butanoate
• 英文别名: 3,4-epoxy-1,3-diphenylbutanone；2-phenacyl-2-phenyloxirane；1-Phenyl-2-(2-phenyloxiran-2-yl)ethanone
• CAS: 133957-56-9
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: XVWHRNOPCNQVGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  190 °C(Press: 1 Torr)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-epoxy-1,3-diphenyl-1-butanoate 以40%的产率得到
  参考文献：
  名称：

  ARAKI, SHUKI;BUTSUGAN, YASUO, BULL. CHEM. SOC. JAP., 64,(1991) N, C. 727-729

  摘要：

  DOI：
• 作为产物：
  描述：

  4-bromo-1,3-diphenyl-3-hydroxybutan-1-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以86%的产率得到3,4-epoxy-1,3-diphenyl-1-butanoate
  参考文献：
  名称：

  Kel'in, A. V.; Kulinkovich, O. G., Russian Journal of Organic Chemistry, 1994, vol. 30, # 2.1, p. 202 - 206

  摘要：

  DOI：

文献信息

• Catalytic Effect of Five-Coordinate Organotin Bromide or Tetraphenylstibonium Bromide on the Chemo- and Stereoselective Addition of Tin Enolate to<i>α</i>-Halo Ketone
  作者：Makoto Yasuda、Tatsuhiro Oh-hata、Ikuya Shibata、Akio Baba、Haruo Matsuda、Noboru Sonoda

  DOI：10.1246/bcsj.68.1180

  日期：1995.4

  tetraphenylstibonium bromide, similarly promoted the selective addition of tin enolates to the carbonyl moiety in α-halo ketones. The reaction with 2-chlorocyclohexanones and the enolates gave chlorohydrins bearing chloro- and hydroxyl groups in the cis-conformation. Chemoselective carbonyl addition to acyclic α-halo ketones was followed by effective cyclization to 2-(2-oxoethyl)oxiranes. The structural and bonding

  两种类型的催化剂，五配位有机锡溴化物和四苯基溴化锑，同样促进了烯醇锡选择性加成到 α-卤代酮的羰基部分。与 2-氯环己酮和烯醇化物的反应得到带有顺式构象的氯和羟基的氯代醇。化学选择性羰基加成到无环 α-卤代酮，然后有效环化成 2-(2-氧乙基) 环氧乙烷。两种催化剂的结构和键合类比可能是导致化学和立体选择性加成的相似催化活性的原因。
• Indium-Induced Reaction of Phenacyl Iodide. Deiodinative Dimerization to β,γ-Epoxy Ketone and Aldol Condensation with Aldehydes
  作者：Shuki Araki、Yasuo Butsugan

  DOI：10.1246/bcsj.64.727

  日期：1991.2

  The reaction of phenacyl iodide with indium metal gave 3,4-epoxy-1,3-diphenyl-1-butanone which, on treatment with silica gel, gave 2,4-diphenylfuran and 2,4-diphenyl-4-oxobutanal. Metallic indium as well as indium(I) iodide were found to mediate the aldol condensation between α-halo ketone and aldehyde.

  苯基碘与金属铟反应生成 3,4-环氧-1,3-二苯基-1-丁酮，用硅胶处理后生成 2,4-二苯基呋喃和 2,4-二苯基-4-氧代丁醛。发现金属铟和碘化铟（I）能介导 α-卤代酮和醛之间的醛醇缩合反应。
• NMR Studies of Five-Coordinate Tin Enolate: An Efficient Reagent for Halo Selective Reaction toward .alpha.-Halo Ketone or .alpha.-Halo Imine
  作者：Makoto Yasuda、Yasuhiro Katoh、Ikuya Shibata、Akio Baba、Haruo Matsuda、Noboru Sonoda

  DOI：10.1021/jo00095a011

  日期：1994.8

  NMR studies of tin enolates 1, in the presence of HMPA, revealed the presence of a five-coordinate O-stannyl enolate 1(h) which contributes to upfield shifts of Sn peaks in the Sn-119 NMR spectrum and increased coupling constants J(Sn-119-C-13), compared with the four-coordinate tin enolate 1(e). The tautomeric equilibrium between C-stannyl ketone 1(k) and O-stannyl enolate 1(e) was changed by the addition of HMPA, the percentage of enol form being increased. The resulting five-coordinate tin enolates 1(h) showed high reactivity and selectivity for halide displacement in reactions with alpha-halo ketones 2. The tin enolates, when coordinated by Bu(4)NBr, effected a selective reaction with alpha-halo imines 5 to give a variety of gamma-imino ketones 6, which were subsequently hydrolyzed to 1,4-diketones or cyclodehydrated to substituted pyrroles 9.
• Kelin A. W., Kulinkowitsch O. G., Zh. organ. khimii, 30 (1994) N 2, S 197-200
  作者：Kelin A. W., Kulinkowitsch O. G.

  DOI：——

  日期：——