(R)-3-methyl-3-phenylpentanoic acid | 4887-10-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-3-methyl-3-phenylpentanoic acid
• 英文别名: (R)-(-)-3-Methyl-3-phenyl-valeriansaeure；(3R)-3-methyl-3-phenylpentanoic acid
• CAS: 4887-10-9
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: ORKUGUZBAAGDJX-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-methyl-3-phenylpentanoic acid 在 三氯化铝 、 氯化亚砜 作用下， 以 苯 为溶剂， 生成 (R)-3-ethyl-3-methyl-indan-1-one
  参考文献：
  名称：

  The absolute configuration of physostigmine

  摘要：

  DOI：

  10.1016/s0040-4020(01)82698-3
• 作为产物：
  描述：

  2,2-dimethyl-5-(1-phenylethylidene)-1,3-dioxane-4,6-dione 在 O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N,N-di-(R,R)-1-phenylethylphosphoric amide 、 硫酸 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.08h， 生成 (R)-3-methyl-3-phenylpentanoic acid
  参考文献：
  名称：

  Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Cu-Catalyzed Conjugate Addition of Dialkylzinc Reagents to 5-(1-Arylalkylidene) Meldrum's Acids

  摘要：

  The asymmetric synthesis of all-carbon benzylic quaternary stereocenters has been successfully achieved through copper-catalyzed addition of dialkylzinc reagents to 5-(1-arylalkylidene) and 5-(dihydroindenylidene) Meldrum's acids in the presence of phosphoramidite ligand. The resulting benzyl-substituted Meldrum's acids and 1,1-disubstituted indanes were obtained in good yields and up to 99% ee. The significance of substituting the position para, meta, and ortho to the electrophilic benzylic center was highlighted. A benzyl Meldrum's acid product was further transformed to a 3,3-disubstituted 1-indanone and a beta,beta-disubstituted pentanoic acid.

  DOI：

  10.1021/ja056692e

文献信息

• Effect of Multinuclear Copper/Aluminum Complexes in Highly Asymmetric Conjugate Addition of Trimethylaluminum to Acyclic Enones
  作者：Kohei Endo、Daisuke Hamada、Sayuri Yakeishi、Takanori Shibata

  DOI：10.1002/anie.201206297

  日期：2013.1.7

  Al and friends: Asymmetric conjugate addition of Me3Al to β,β‐disubstituted α,β‐unsaturated ketones in the presence copper and L1 leads to a highly efficient construction of an all‐carbon‐substituted chiral quaternary center. This result is the first example of an asymmetric conjugate addition of Me3Al to acyclic enones to give a chiral quaternary carbon center with excellent yield and enantioselectivity

  Al和朋友：在铜和L1存在下，Me 3 Al不对称地共轭添加到β，β-二取代的α，β-不饱和酮中，导致高效构建全碳取代的手性季中心。该结果是在温和的反应条件下将Me 3 Al不对称共轭加成到无环烯酮上以得到具有优异收率和对映选择性的手性季碳中心的第一个例子。
• Halomethyl-metal compounds. LXIII. Insertion of phenyl(bromodichloromethyl)mercury-derived dichlorocarbene into benzylic carbon-hydrogen bonds. Stereochemistry and mechanism
  作者：Dietmar. Seyferth、Ying Ming. Cheng

  DOI：10.1021/ja00801a039

  日期：1973.10
• The absolute configuration of physostigmine
  作者：R.K. Hill、G.R. Newkome

  DOI：10.1016/s0040-4020(01)82698-3

  日期：1969.1
• Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Cu-Catalyzed Conjugate Addition of Dialkylzinc Reagents to 5-(1-Arylalkylidene) Meldrum's Acids
  作者：Eric Fillion、Ashraf Wilsily

  DOI：10.1021/ja056692e

  日期：2006.3.1

  The asymmetric synthesis of all-carbon benzylic quaternary stereocenters has been successfully achieved through copper-catalyzed addition of dialkylzinc reagents to 5-(1-arylalkylidene) and 5-(dihydroindenylidene) Meldrum's acids in the presence of phosphoramidite ligand. The resulting benzyl-substituted Meldrum's acids and 1,1-disubstituted indanes were obtained in good yields and up to 99% ee. The significance of substituting the position para, meta, and ortho to the electrophilic benzylic center was highlighted. A benzyl Meldrum's acid product was further transformed to a 3,3-disubstituted 1-indanone and a beta,beta-disubstituted pentanoic acid.