(R)-2-(1-(3,4-dichlorophenyl)-1-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1338922-79-4

• 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)-2-(1-(3,4-dichlorophenyl)-1-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-[(1R)-1-(3,4-dichlorophenyl)-1-phenylbutyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1338922-79-4
• 化学式: C₂₂H₂₇BCl₂O₂
• 分子量: 405.172
• InChiKey: NCXXKSJCOAALML-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(1-(3,4-dichlorophenyl)-1-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以68%的产率得到(S)-1-(3,4-dichlorophenyl)-1-phenylbutan-1-ol
  参考文献：
  名称：

  Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation–Protodeboronation Methodology

  摘要：

  The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.

  DOI：

  10.1021/ol202251p
• 作为产物：
  描述：

  3,4-二氯苯硼酸 在 仲丁基锂 作用下， 以 乙醚 、 正己烷 、 环己烷 为溶剂， 反应 19.5h， 生成 (R)-2-(1-(3,4-dichlorophenyl)-1-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation–Protodeboronation Methodology

  摘要：

  The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.

  DOI：

  10.1021/ol202251p

文献信息

• Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation–Protodeboronation Methodology
  作者：Stefan Roesner、Javier Mansilla Casatejada、Tim G. Elford、Ravindra P. Sonawane、Varinder K. Aggarwal

  DOI：10.1021/ol202251p

  日期：2011.11.4

  The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.