(2R)-3-(Benzyloxy)-2-methylpropanoic acid chloride | 84801-99-0

• 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: (2R)-3-(Benzyloxy)-2-methylpropanoic acid chloride
• 英文别名: (2R)-3-(Benzyloxy)-2-methylpropanoyl chloride；(2R)-2-methyl-3-phenylmethoxypropanoyl chloride
• CAS: 84801-99-0
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: QPGUOENMCWIDBN-SECBINFHSA-N

物化性质

• 沸点：
  280.9±23.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (2R)-3-(Benzyloxy)-2-methylpropanoic acid chloride 以 四氢呋喃 、 乙醚 为溶剂， 生成 (S)-4-(benzyloxy)-2,3-dimethyl-1-butene
  参考文献：
  名称：

  Total synthesis of (+)-phyllanthocin

  摘要：

  DOI：

  10.1021/ja00380a035
• 作为产物：
  描述：

  (-)-(R)-3-benzyloxy-2-methylpropionic acid 在 草酰氯 作用下， 以 苯 为溶剂， 生成 (2R)-3-(Benzyloxy)-2-methylpropanoic acid chloride
  参考文献：
  名称：

  Total synthesis of (+)-phyllanthocin

  摘要：

  DOI：

  10.1021/ja00380a035

文献信息

• Synthetic applications of titanocene methylene complexes: selective formation of ketone enolates and their reactions
  作者：John R. Stille、Robert H. Grubbs

  DOI：10.1021/ja00344a048

  日期：1983.3
• Ligand-Enabled Cross-Coupling of C(sp³)–H Bonds with Arylsilanes
  作者：Jian He、Ryosuke Takise、Haiyan Fu、Jin-Quan Yu

  DOI：10.1021/jacs.5b00890

  日期：2015.4.15

  Pd(II)-catalyzed cross-coupling of C(sp(3))-H bonds with organosilicon coupling partners has been achieved for the first time. The use of a newly developed quinoline-based ligand is essential for the cross-coupling reactions to proceed.
• Total synthesis of (+)-phyllanthocin
  作者：Paul R. McGuirk、David B. Collum

  DOI：10.1021/ja00380a035

  日期：1982.8
• Intramolecular Nucleophilic Acyl Substitution Reactions Mediated by Samarium(II) Iodide: A Convergent Approach to the Preparation of Enantiomerically Enriched 4-Hydroxy Ketones from 3-Iodopropyl Carboxylates
  作者：Gary A. Molander、Sagar R. Shakya

  DOI：10.1021/jo00091a039

  日期：1994.6

  Intramolecular nucleophilic acylsubstitution (INAS) reactions of substituted 3-iodopropyl carboxylates have been achieved using samarium(II) iodide (SmI2) in the presence of an iron(III) catalyst. Diverse ester starting materials containing stereogenic centers placed in varying positions on the substrates have been converted to acyclic 4-hydroxy ketone derivatives in good yields using this method. No racemization of stereogenic centers alpha to the carbonyl was observed in any of the reactions examined. Consequently, the method serves as a convenient, high-yield synthesis of functionalized, enantiomerically enriched acyclic ketones possessing stereogenic centers far removed from one another.