1,5-二羟基-1,5-二苯基-戊烷-3-酮 | 121598-90-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1,5-二羟基-1,5-二苯基-戊烷-3-酮
• 英文名称: 1,5-dihydroxy-1,5-diphenyl-pentan-3-one
• 英文别名: 1,5-Dihydroxy-1,5-diphenyl-pentan-3-on；1,5-Dihydroxy-1,5-diphenylpentan-3-one
• CAS: 121598-90-1
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: UZRFVEOTPRNEAK-UHFFFAOYSA-N

物化性质

• 沸点：
  461.3±40.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  trans,trans-1,2,4,5-diepoxy-1,5-diphenylpentan-3-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以39.8%的产率得到3-hydroxy-3-phenyl-1-[(2R,3S)-3-phenyloxiran-2-yl]propan-1-one
  参考文献：
  名称：

  Photochemically and thermally induced free-radical reactions of .alpha.,.beta.-epoxy ketones with tributyltin hydride: selective C.alpha.-O bond cleavage of oxiranylmethyl radicals derived from .alpha.,.beta.-epoxy ketones

  摘要：

  Free-radical reactions of alpha,beta-epoxy ketones with tributyltin hydride have been studied. These substances were selectively converted to beta-hydroxy ketones under both photochemical and thermal conditions. The photoreaction is initiated by hydrogen abstraction of an epoxy ketone triplet from tributyltin hydride, while azoisbutyronitrile is used as an initiator for the thermal reaction. In general, the photoreaction conditions are particularly useful for aroyl-substituted epoxy ketones while the thermal conditions are applicable to a variety of epoxy ketones. It was also found that the epoxy esters and epoxy alcohols did not undergo the ring-opening reaction under the similar conditions. Tributyltin radical attack on the carbonyl of epoxy ketones is a key process for both the photoreaction and the thermal reaction. Regioselective ring opening of the resulting oxiranylmethyl radical finally produces beta-hydroxy ketones. In order to capture the free-radical intermediates, the reaction of epoxy ketones with allyltributyltin was conducted. The isolation of alpha-allylated beta-hydroxy ketones is interpreted by the involvement of a novel 1,5-tributyltin transfer.

  DOI：

  10.1021/jo00046a016

文献信息

• Novel synthesis of cyclobutanone derivatives via dimetalation of iminium ions with the TiCl4–trialkylamine reagent system
  作者：Mariappan Periasamy、K. Natarajan Jayakumar、Pandi Bharathi

  DOI：10.1039/b103112k

  日期：——

  Iminium salts are generated in situ, react with TiCl4-trialkylamines, and diaryl ketones to produce 3,3-diaryl-cyclobutanones in moderate to good yields.

  亚硝酸盐原位生成，与TiCl4-三烷基胺和二芳基酮反应生成3,3-二芳基-环丁酮，产率中等至良好。
• Studies on organosilicon chemistry. 98. Synthesis and consecutive double alkylation reactions of (2-siloxyallyl)silanes as the synthetic equivalent of acetone .alpha.,.alpha.'-dianion
  作者：Akira Hosomi、Hisashi Hayashida、Yoshinori Tominaga

  DOI：10.1021/jo00275a004

  日期：1989.7
• Schoepf; Thierfelder, Justus Liebigs Annalen der Chemie, 1935, vol. 518, p. 127,147
  作者：Schoepf、Thierfelder

  DOI：——

  日期：——
• Encapsulating epoxy resin composition
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0403022B1

  公开（公告）日：1996-11-13
• US5149730A
  申请人：——

  公开号：US5149730A

  公开（公告）日：1992-09-22