(R)-3-(4,4-dimethyl-3-phenylpentanoyl)-4,4-diphenyl-2-oxazolidinone | 327025-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-(4,4-dimethyl-3-phenylpentanoyl)-4,4-diphenyl-2-oxazolidinone
• 英文别名: 3-[(3R)-4,4-dimethyl-3-phenylpentanoyl]-4,4-diphenyl-1,3-oxazolidin-2-one
• CAS: 327025-33-2
• 化学式: C₂₈H₂₉NO₃
• 分子量: 427.543
• InChiKey: ZHTRGXCJEMIJSG-DEOSSOPVSA-N

物化性质

• 熔点：
  110-115 °C
• 沸点：
  583.1±50.0 °C(predicted)
• 密度：
  1.157±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：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(4,4-dimethyl-3-phenylpentanoyl)-4,4-diphenyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以93%的产率得到(R)-4,4-dimethyl-3-phenylpentanoic acid
  参考文献：
  名称：

  Unprecedented Effects of Achiral Oxazolidinones on Enantioselective Radical-Mediated Conjugate Additions Using a Chiral Zinc Triflate

  摘要：

  [GRAPHICS]A role of achiral oxazolidinones to enhance the enantioselectivity in reactions of N-cinnamoyloxazolidinones with alkyl radicals promoted by a chiral Lewis acid Is described. Efficient enantioselective radical-mediated conjugate additions of N-cinnamoyloxazolidinone can be realized by use of a chiral zinc triflate generated from a readily prepared chiral bisoxazoline and an achiral oxazolidinone. The NH moiety of achiral oxazolidinones is found to be necessary to enhance the enantioselectivity.

  DOI：

  10.1021/ol006927l
• 作为产物：
  描述：

  2-氨基-2,2-二苯基-1-乙醇 在 正丁基锂 、 4,4-diphenyloxazolidin-2-one 、 zinc trifluoromethanesulfonate 、 三乙胺 、 (S,S)-2,2'-(1-ethylpropylidene)bis(4-phenyl-4,5-dihydrooxazole) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 39.5h， 生成 (R)-3-(4,4-dimethyl-3-phenylpentanoyl)-4,4-diphenyl-2-oxazolidinone
  参考文献：
  名称：

  Unprecedented Effects of Achiral Oxazolidinones on Enantioselective Radical-Mediated Conjugate Additions Using a Chiral Zinc Triflate

  摘要：

  [GRAPHICS]A role of achiral oxazolidinones to enhance the enantioselectivity in reactions of N-cinnamoyloxazolidinones with alkyl radicals promoted by a chiral Lewis acid Is described. Efficient enantioselective radical-mediated conjugate additions of N-cinnamoyloxazolidinone can be realized by use of a chiral zinc triflate generated from a readily prepared chiral bisoxazoline and an achiral oxazolidinone. The NH moiety of achiral oxazolidinones is found to be necessary to enhance the enantioselectivity.

  DOI：

  10.1021/ol006927l

文献信息

• Unprecedented Effects of Achiral Oxazolidinones on Enantioselective Radical-Mediated Conjugate Additions Using a Chiral Zinc Triflate
  作者：Masatoshi Murakata、Hideyuki Tsutsui、Osamu Hoshino

  DOI：10.1021/ol006927l

  日期：2001.1.1

  [GRAPHICS]A role of achiral oxazolidinones to enhance the enantioselectivity in reactions of N-cinnamoyloxazolidinones with alkyl radicals promoted by a chiral Lewis acid Is described. Efficient enantioselective radical-mediated conjugate additions of N-cinnamoyloxazolidinone can be realized by use of a chiral zinc triflate generated from a readily prepared chiral bisoxazoline and an achiral oxazolidinone. The NH moiety of achiral oxazolidinones is found to be necessary to enhance the enantioselectivity.