Acetic acid 1,1-dimethyl-2-oxo-4-phenyl-but-3-ynyl ester | 87064-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid 1,1-dimethyl-2-oxo-4-phenyl-but-3-ynyl ester
• 英文别名: 2-Methyl-3-oxo-5-phenylpent-4-yn-2-yl acetate；(2-methyl-3-oxo-5-phenylpent-4-yn-2-yl) acetate
• CAS: 87064-06-0
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: UOZAHEPTVPCFAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid 1,1-dimethyl-2-oxo-4-phenyl-but-3-ynyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 2,2-二甲基-5-苯基呋喃-3-酮
  参考文献：
  名称：

  布地那农和吉巴伐林的新合成

  摘要：

  描述了两个3（2H）-呋喃酮天然产物Bullatenone（1）和geiparvarin（2）的新的便捷合成方法，涉及相应易得的炔酮的水合作用。这些最好由Pd（II）-Cu（I）催化的偶联过程制得。

  DOI：

  10.1016/s0040-4039(00)81859-6
• 作为产物：
  描述：

  α-Acetoxyisobutyryl chloride 、 lithium phenylacetylide 以 四氢呋喃 为溶剂， 生成 Acetic acid 1,1-dimethyl-2-oxo-4-phenyl-but-3-ynyl ester
  参考文献：
  名称：

  布地那农和吉巴伐林的新合成

  摘要：

  描述了两个3（2H）-呋喃酮天然产物Bullatenone（1）和geiparvarin（2）的新的便捷合成方法，涉及相应易得的炔酮的水合作用。这些最好由Pd（II）-Cu（I）催化的偶联过程制得。

  DOI：

  10.1016/s0040-4039(00)81859-6

文献信息

• Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 1. Reactions with organocopper reagents
  作者：Thomas R. Barbee、Kim F. Albizati

  DOI：10.1021/jo00024a014

  日期：1991.11

  A series of alpha-nucleofuge alpha',beta'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared. Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the alpha-nucleofuge or conjugate addition. Good alpha-nucleofuges favored the reduction pathway while poorer nucleofuges favored conjugate addition.
• Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 2. Reactions with malonate anion. Concerning the mechanism of the Favorskii rearrangement
  作者：Thomas R. Barbee、Hedeel Guy、Mary Jane Heeg、Kim F. Albizati

  DOI：10.1021/jo00024a015

  日期：1991.11

  The scope and limiations of the reaction of alpha'-nucleofuge alpha,beta-unsaturated ketones with sodium dimethyl malonate has been studied systematically. The substrates with good nucleofuges (halides, mesylate) give cyclopropanols upon reaction with malonate anion by way of a conjugate Favorskii reaction. In reactions with substrates containing the poorer nucleofuge (acetoxy) conjugate addition proceeded without entering the Favorskii manifold. Concerning the mechanism of the Favorskii reaction, it is suggested that the loss of the nucleofuge occurs to give a 2-oxyallyl cation, but that disrotatory ring closure is facile and the only products observed result from nucleophilic trapping of cyclopropanones to yield cyclopropanols in fair to good yield.
• Jackson, Richard F. W.; Raphael, Ralph A., Journal of the Chemical Society. Perkin transactions I, 1984, # 3, p. 535 - 539
  作者：Jackson, Richard F. W.、Raphael, Ralph A.

  DOI：——

  日期：——
• New syntheses of bullatenone and geiparvarin
  作者：Richard Fw Jackson、Ralph A Raphael

  DOI：10.1016/s0040-4039(00)81859-6

  日期：1983.1

  New convenient syntheses of two 3(2H)-furanone natural products bullatenone (1) and geiparvarin (2) are described involving the hydration of the corresponding readily accessible acetylenic ketones. These are best made by a Pd (II) - Cu (I) catalysed coupling process.

  描述了两个3（2H）-呋喃酮天然产物Bullatenone（1）和geiparvarin（2）的新的便捷合成方法，涉及相应易得的炔酮的水合作用。这些最好由Pd（II）-Cu（I）催化的偶联过程制得。