[(2R)-3-iodo-2-methylpropyl] (2R)-2-methyl-3-phenylpropanoate | 155675-21-1

• 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-iodo-2-methylpropyl] (2R)-2-methyl-3-phenylpropanoate
• CAS: 155675-21-1
• 化学式: C₁₄H₁₉IO₂
• 分子量: 346.208
• InChiKey: DPARCEXLOGAGTO-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-iodo-2-methylpropyl] (2R)-2-methyl-3-phenylpropanoate 在 吡啶 、 4-二甲氨基吡啶 、 samarium diiodide 、 tris(dibenzoylmethano)iron(III) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2R,5S)-6-Acetoxy-2,5-dimethyl-1-phenylhexan-3-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00091a039
• 作为产物：
  描述：

  2-methyl-3-phenylpropionic acid 在 草酰氯 作用下， 生成 [(2R)-3-iodo-2-methylpropyl] (2R)-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00091a039