1-Dodecanone, 1-phenyl-2-(2-phenylethyl)- | 194785-53-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 1-Dodecanone, 1-phenyl-2-(2-phenylethyl)-
• 英文别名: 1-phenyl-2-(2-phenylethyl)dodecan-1-one
• CAS: 194785-53-0
• 化学式: C₂₆H₃₆O
• 分子量: 364.571
• InChiKey: XNAQFWAJZHOXFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  反式-查耳酮 在 六甲基磷酰三胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 30.0h， 生成 1-Dodecanone, 1-phenyl-2-(2-phenylethyl)-
  参考文献：
  名称：

  One- and Two-Electron Reactions from the Rearrangement of α-Ketocyclopropanes by O-Stannyl Ketyls

  摘要：

  This work summarizes an investigation of the bifunctional reactions of tin(IV) enolates and radicals derived from the cleavage rearrangement of ketocyclopropanes with tributyltin hydride. The intermediates provide an unparalleled dual reactivity in synthesis, allowing for independent transformations with both electrophiles and radicophiles. Reactions of the enolate with aldehydes led to aldol products in diastereoselectivities up to 20:1 favoring the erythro product. Reactions with alkyl halides were also successful, constructing new carbon-carbon bonds by a nucleophilic displacement reaction. These reactions provide a neutral, mild, and novel alternative to the classical methods of ketone enolate alkylation performed with hindered bases. Finally, the radical portion of the cleaved intermediates, separated from the enolate by a methylene unit, was reacted with allylstannanes to prepare new gamma-carbon bonds to an allyl unit. Overall, these new trialkyltin-associated radical anion intermediates allow entry into the rapidly developing manifold of one- and two-electron reactions.

  DOI：

  10.1021/jo971287u

文献信息

• Reactions of Tin(IV) Enolates and Radicals Derived from the Tin Hydride Scission of Cyclopropyl Ketones
  作者：Eric J. Enholm、Zhaozhong J. Jia

  DOI：10.1021/jo970914c

  日期：1997.8.1
• One- and Two-Electron Reactions from the Rearrangement of α-Ketocyclopropanes by <i>O</i>-Stannyl Ketyls
  作者：Eric J. Enholm、Zhaozhong J. Jia

  DOI：10.1021/jo971287u

  日期：1997.12.1

  This work summarizes an investigation of the bifunctional reactions of tin(IV) enolates and radicals derived from the cleavage rearrangement of ketocyclopropanes with tributyltin hydride. The intermediates provide an unparalleled dual reactivity in synthesis, allowing for independent transformations with both electrophiles and radicophiles. Reactions of the enolate with aldehydes led to aldol products in diastereoselectivities up to 20:1 favoring the erythro product. Reactions with alkyl halides were also successful, constructing new carbon-carbon bonds by a nucleophilic displacement reaction. These reactions provide a neutral, mild, and novel alternative to the classical methods of ketone enolate alkylation performed with hindered bases. Finally, the radical portion of the cleaved intermediates, separated from the enolate by a methylene unit, was reacted with allylstannanes to prepare new gamma-carbon bonds to an allyl unit. Overall, these new trialkyltin-associated radical anion intermediates allow entry into the rapidly developing manifold of one- and two-electron reactions.