3-丁基-1-苯基-1-庚酮 | 127698-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-丁基-1-苯基-1-庚酮
• 英文名称: 3-butyl-1-phenyl-1-heptanone
• 英文别名: 3-Butyl-1-phenylheptan-1-one
• CAS: 127698-54-8
• 化学式: C₁₇H₂₆O
• 分子量: 246.393
• InChiKey: ALVWOXCVBGMUFT-UHFFFAOYSA-N

物化性质

• 沸点：
  339.0±11.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  苯甲酸乙酯 、 二溴甲烷 生成 苯庚酮 、 苯己酮 、 3-丁基-1-苯基-1-庚酮 、 2-溴苯乙酮
  参考文献：
  名称：

  Ester homologation revisited: a reliable, higher yielding and better understood procedure

  摘要：

  Enolate anions 3 and 6, prepared via enolization of a-bromo and dibromo ketones 4 and 5 were converted m high yield to ynolate anions 10 by respective addition of lithium tetramethylpiperidide (to effect deprotonation, 3 --> 7) or butyllithium (to effect metal-halogen exchange, 6 --> 7). Mixtures of such enolates were abo obtainable from esters 1 m a large-scale (25 mmol) via in situ formation and addition of lithiodibromomethane (from methylene bromide and lithium tetramethylpiperidide), followed by treatment of the resulting adducts with lithium hexamethyldisilazide to ensure complete enolization. Addition of sec-butyllithium and n-butyllithium to effect ynolate anion formation, followed by quenching of the reaction mixtures into acidic ethanol, reproducibly afforded homologated esters 8 in 67-90% yield. Demonstrated for ethyl esters 1 having the carbethoxy moiety attached to primary, secondary, tertiary, aryl, and alkenyl groups, this general procedure provides a convenient, large-scale alternative to the classical Arndt-Eistert sequence.

  DOI：

  10.1021/jo00052a038

文献信息

• Ester homologation revisited: a reliable, higher yielding and better understood procedure
  作者：Conrad J. Kowalski、Rajarathnam E. Reddy

  DOI：10.1021/jo00052a038

  日期：1992.12

  Enolate anions 3 and 6, prepared via enolization of a-bromo and dibromo ketones 4 and 5 were converted m high yield to ynolate anions 10 by respective addition of lithium tetramethylpiperidide (to effect deprotonation, 3 --> 7) or butyllithium (to effect metal-halogen exchange, 6 --> 7). Mixtures of such enolates were abo obtainable from esters 1 m a large-scale (25 mmol) via in situ formation and addition of lithiodibromomethane (from methylene bromide and lithium tetramethylpiperidide), followed by treatment of the resulting adducts with lithium hexamethyldisilazide to ensure complete enolization. Addition of sec-butyllithium and n-butyllithium to effect ynolate anion formation, followed by quenching of the reaction mixtures into acidic ethanol, reproducibly afforded homologated esters 8 in 67-90% yield. Demonstrated for ethyl esters 1 having the carbethoxy moiety attached to primary, secondary, tertiary, aryl, and alkenyl groups, this general procedure provides a convenient, large-scale alternative to the classical Arndt-Eistert sequence.