4-hydroxy-4-methyl-3-phenylpentanoic acid γ-lactone | 13133-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-hydroxy-4-methyl-3-phenylpentanoic acid γ-lactone
• 英文别名: β-phenyl-γγ-dimethylbutyrolactone；(+/-)-dihydro-5,5-dimethyl-4-phenyl-2(3H)-furanone；4-methyl-3-phenyl-γ-valerolactone；4,4-dimethyl-3-phenyltetranolide；5,5-dimethyl-4-phenyl-dihydro-furan-2-one；β-Phenyl-γ-methyl-γ-valerolacton；5,5-dimethyl-4-phenyloxolan-2-one
• CAS: 13133-96-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: CULAWTLHZMUYLR-UHFFFAOYSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  140 °C(Press: 0.5 Torr)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4-methyl-3-phenylpentanoic acid γ-lactone 在 lithium aluminium tetrahydride 作用下， 生成 2-methyl-3-phenylpentane-2,5-diol
  参考文献：
  名称：

  Cyclization of ylidenemalononitriles. V. Formation of substituted .gamma.-lactones

  摘要：

  DOI：

  10.1021/jo01283a002
• 作为产物：
  描述：

  3-chloro-3-phenyl-3H-diazirine 在 盐酸 、 氢氧化钾 、 氢气 作用下， 以 甲苯 为溶剂， 生成 4-hydroxy-4-methyl-3-phenylpentanoic acid γ-lactone
  参考文献：
  名称：

  环丙烯羧酸的开环和扩环

  摘要：

  由氯苯基二嗪1开始制备3，3-二甲基-2-苯基-环丙烯羧酸4。用酸4产生开链羧酸5、6和7。亚硫酰氯生成环丁烯酮10，DCC生成酸酐11和11。 13

  DOI：

  10.1016/s0040-4039(00)94983-9

文献信息

• Improved enantioselection for chiral dirhodium(II) carboxamide-catalysed carbon-hydrogen insertion reactions of tertiary alkyl diazoacetates
  作者：Michael P. Doyle、Qi-Lin Zhou、Conrad E. Raab、Gregory H.P. Roos

  DOI：10.1016/0040-4039(95)00927-5

  日期：1995.7

  Enantiocontrol in CH insertion reactions of 3° alkyl diazoacetates, which is highly dependent on the catalyst ligand, is greatly enhanced with the use of dirhodium(II) tetrakis[methyl 1-acetylimidazolidin-2-one-4(S)-carboxylate], Rh2(4S-MACIM)4.

  高度依赖于催化剂配体的3°重氮烷基乙酸CH插入反应中的对映体控制通过使用四[甲基1-乙酰基咪唑烷二甲基-2-酮-4（S）-羧酸盐]（II）来大大增强]，Rh 2（4S-MACIM）4。
• Julia,M. et al., Bulletin de la Societe Chimique de France, 1960, p. 304 - 312
  作者：Julia,M. et al.

  DOI：——

  日期：——
• Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions
  作者：Gary P. Lutz、Hua Du、Donald J. Gallagher、Peter Beak

  DOI：10.1021/jo952223r

  日期：1996.1.1

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.
• Jalander, Lars; Broms, Merete, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 6, p. 371 - 376
  作者：Jalander, Lars、Broms, Merete

  DOI：——

  日期：——
• Jalander, Lars; Iambolieva, Kostadinka; Sundstroem, Viola, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 10, p. 715 - 720
  作者：Jalander, Lars、Iambolieva, Kostadinka、Sundstroem, Viola

  DOI：——

  日期：——