(Z)-4-(1-(dicyclohexylboraneyl)-2-(1,3-diethyl-1,3-dihydro-2H-benzo[d][1,3,2]diazaborol-2-yl)vinyl)-N,N-dimethylaniline | 1432663-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-4-(1-(dicyclohexylboraneyl)-2-(1,3-diethyl-1,3-dihydro-2H-benzo[d][1,3,2]diazaborol-2-yl)vinyl)-N,N-dimethylaniline
• CAS: 1432663-27-8
• 化学式: C₃₂H₄₇B₂N₃
• 分子量: 495.367
• InChiKey: FKELHKZMAYZXQB-QCWLDUFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.23
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.72
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-(4'-(dimethylamino)phenylethynyl)-1,3-diethyl-1,3,2-benzodiazaborole 、 bis(cyclohexanyl)borane 以 乙醚 为溶剂， 反应 4.0h， 生成 (Z)-4-(2-(dicyclohexylboraneyl)-2-(1,3-diethyl-1,3-dihydro-2H-benzo[d][1,3,2]diazaborol-2-yl)vinyl)-N,N-dimethylaniline 、 (Z)-4-(1-(dicyclohexylboraneyl)-2-(1,3-diethyl-1,3-dihydro-2H-benzo[d][1,3,2]diazaborol-2-yl)vinyl)-N,N-dimethylaniline
  参考文献：
  名称：

  Hydroboration of Alkyne‐Functionalized 1,3,2‐Benzodiazaboroles

  摘要：

  AbstractReactions of equimolar amounts of dicyclohexylborane (DCB) with a series of 2‐alkynyl‐1,3‐diethyl‐1,3,2‐benzodiazaboroles R–C≡C–B(NEt)2C6H4 (1: R = nBu, 2: R = tBu, 3: R = Ph, 4: R = p‐Me2NC6H4, 5: R = p‐MeOC6H4) regioselectively afforded the 1,1‐diborylalkenes (Z)‐R(H)C=C{(B{NEt}2C6H4)B(c‐C6H11)2} (7a–11a) as the result of a cis‐addition of the BH bond of the borane to the C≡C triple bond in compounds 1 to 5. In contrast to this, reaction of Me3Si–C≡C–B(NEt)2C6H4 (6) with HB(c‐C6H11)2 yielded a 2.5:1 mixture of the 1,2‐diborylated alkene (Z)‐Me3Si{(c‐C6H11)2B}C=CHB(NEt)2C6H4 (12b) and the 1,1‐regioisomer (Z)‐Me3Si(H)C=C{B(NEt)2C6H4}{B(c‐C6H11)2} (12a). These results were rationalized by the differing π‐acceptor qualities of the benzodiazaborolyl and trimethylsilyl substituents at the C≡C triple bond in compounds 1 to 6. The novel products 7–12 were characterized by elemental analysis, mass spectrometry and NMR spectroscopy (1H, 11B, and 13C NMR). The molecular structures of 9b and 12b were substantiated by single‐crystal X‐ray diffraction analysis.

  DOI：

  10.1002/ejic.201201489