3-Benzoyl-2,3-dimethyl-4-(trimethylsilyl)-1-butene | 55532-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Benzoyl-2,3-dimethyl-4-(trimethylsilyl)-1-butene
• 英文别名: 2,3-Dimethyl-1-phenyl-2-(trimethylsilylmethyl)but-3-en-1-one
• CAS: 55532-01-9
• 化学式: C₁₆H₂₄OSi
• 分子量: 260.451
• InChiKey: YFIHCKJSIKWZSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-dimethyl-1,4-bis(trimethylsilyl)-2-butene 、 苯甲酰氯 在 indium(III) chloride 作用下， 生成 3-Benzoyl-2,3-dimethyl-4-(trimethylsilyl)-1-butene
  参考文献：
  名称：

  Synthese nouvelle d'allylcetones par voie organosilicique

  摘要：

  DOI：

  10.1016/s0022-328x(00)80694-4

文献信息

• Chemistry of substituted (2-butene-1,4-diyl)magnesium: a facile approach to complex carbocycles, functionalized ketones and alcohols, and silicon-containing heterocycles
  作者：Reuben D. Rieke、Heping Xiong

  DOI：10.1021/jo00009a034

  日期：1991.4

  Highly reactive magnesium reacts with a wide variety of substituted 1,3-dienes to give the corresponding substituted (2-butene-1,4-diyl)magnesium complexes. Reactions of symmetrical (2-butene-1,4-diyl)magnesium with alpha,omega-alkylene dihalides form three-, four-, five-, and six-membered carbocycles. Significantly, the cyclizations are always stereospecific and completely regioselective. Depending on the initial 1,3-diene and specific electrophiles, uncyclized products can be obtained. Stepwise reactions of (2,3-dimethyl-2-butene-1,4-diyl)magnesium with two different electrophiles afford polyfunctionalized ketones with the generation of a quaternary center. Formal 1,2-additions can be effected in this manner. Substituted five- and six-membered cyclic ketones can also be synthesized in one step by this approach. Treatment of unsymmetrical (2-butene-1,4-diyl)magnesium complexes with triorganosilyl chlorides followed by cyclohexanone results in additions across a terminal double bond with high regioselectivity. Silicon-containing heterocycles or spiro compounds can be readily synthesized by using the bis-Grignard reagents.
• Facile formation of substituted 2-butene-1,4-diylmagnesium using highly reactive magnesium. A simple approach to complex carbocycles and functionalized ketones
  作者：Heping Xiong、Reuben D. Rieke

  DOI：10.1021/jo00275a001

  日期：1989.7
• Synthese nouvelle d'allylcetones par voie organosilicique
  作者：R. Calas、J. Dunogues、J.-P. Pillot、C. Biran、F. Pisciotti、B. Arreguy

  DOI：10.1016/s0022-328x(00)80694-4

  日期：1975.2