1,4-diphenyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)but-3-en-2-ol | 1315278-82-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,4-diphenyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)but-3-en-2-ol
• CAS: 1315278-82-0
• 化学式: C₂₂H₂₇BO₃
• 分子量: 350.266
• InChiKey: FNFLQLLWEVJNTO-CYVLTUHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,4-diphenyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)but-3-en-2-ol 、 氨基邻苯二甲胺 在 碘苯二乙酸 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-(1-hydroxy-2-phenylethyl)-3-phenyl-2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)aziridin-1-yl)isoindoline-1,3-dione 、 2-(2-(1-hydroxy-2-phenylethyl)-3-phenyl-2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)aziridin-1-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Diastereoselective Aziridination of 2-B(pin)-Substituted Allylic Alcohols: An Efficient Approach to Novel Organoboron Compounds

  摘要：

  We report that 2-B(pin)-substituted allylic alcohols are good substrates for diastereoselective aziridinations in the presence of Phl(OAc)(2) and N-aminophthalimide. Under the aziridination conditions, the valuable B-C bond remains Intact, affording a variety of novel boron-substituted aziridines In good yields and excellent diastereoselectivities. Oxidation of the aziridine B-C bond enables generation of syn-1,3-aminohydroxy-2-ketones with high diastereoselectivity.

  DOI：

  10.1021/ol202588g
• 作为产物：
  描述：

  2-苯基-1-乙炔硼酸频那醇酯 在 Dimethylzinc 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 1,4-diphenyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)but-3-en-2-ol
  参考文献：
  名称：

  Diastereoselective Aziridination of 2-B(pin)-Substituted Allylic Alcohols: An Efficient Approach to Novel Organoboron Compounds

  摘要：

  We report that 2-B(pin)-substituted allylic alcohols are good substrates for diastereoselective aziridinations in the presence of Phl(OAc)(2) and N-aminophthalimide. Under the aziridination conditions, the valuable B-C bond remains Intact, affording a variety of novel boron-substituted aziridines In good yields and excellent diastereoselectivities. Oxidation of the aziridine B-C bond enables generation of syn-1,3-aminohydroxy-2-ketones with high diastereoselectivity.

  DOI：

  10.1021/ol202588g