2-(4-methoxyphenylethynyl)-1,3-diethyl-1,3,2-benzodiazaborole | 1159194-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(4-methoxyphenylethynyl)-1,3-diethyl-1,3,2-benzodiazaborole
• 英文别名: 1,3-Diethyl-2-[2-(4-methoxyphenyl)ethynyl]-1,3,2-benzodiazaborole
• CAS: 1159194-93-0
• 化学式: C₁₉H₂₁BN₂O
• 分子量: 304.2
• InChiKey: QOMOUZBERPUFTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenylethynyl)-1,3-diethyl-1,3,2-benzodiazaborole 、 bis(cyclohexanyl)borane 以 乙醚 为溶剂， 反应 4.0h， 生成 (Z)-2-(1-(dicyclohexylboraneyl)-2-(4-methoxyphenyl)vinyl)-1,3-diethyl-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole 、 (Z)-2-(2-(dicyclohexylboraneyl)-2-(4-methoxyphenyl)vinyl)-1,3-diethyl-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole
  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
• 作为产物：
  描述：

  2-bromo-1,3-diethyl-1,3,2-benzodiazaborole 、 4-乙炔基苯甲醚 在 n-butyllithium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以69%的产率得到2-(4-methoxyphenylethynyl)-1,3-diethyl-1,3,2-benzodiazaborole
  参考文献：
  名称：

  对2-芳基乙炔基-1,3,2-二氮杂硼烷的合成，结构，光物理和计算研究。

  摘要：

  新的2-芳基炔基苯并-1,3,2-二氮杂硼烷，2-（4'-XC（6）H（4）C [三键，长度为m-破折号] C）-1,3-Et（2） -1,3,2-N（2）BC（6）H（4）（X = Me; MeO; MeS; Me（2）N）由B-溴二氮杂硼酸酯2-Br-1,3-制备Et（2）-1,3,2-N（2）BC（6）H（4），带有适当的锂化芳基乙炔，ArC 3键，长度为m-CLi。和的分子结构通过X射线衍射研究确定。对这些diazaboroles的紫外可见光谱和发光光谱研究表明，强烈的蓝/紫荧光具有非常大的量子产率，为0.89-0.99。实验结果得到DFT和TD-DFT计算的补充。相对于5900-7300 cm（-1）范围内的斯托克斯位移，仅2600 cm（-1）的斯托克斯位移由（X = H）所发现的不同电子结构部分地解释了。HOMO主要位于其中的二氮杂硼烯丙基中的芳基上，而对于所有化合物而言，L

  DOI：

  10.1039/b821208b

文献信息

• UV-Photoelectron Spectroscopic Studies on 2-Arylethynyl-1,3,2-benzodiazaboroles
  作者：Anna Chrostowska、Małgorzata Maciejczyk、Alain Dargelos、Patrick Baylère、Lothar Weber、Vanessa Werner、Daniel Eickhoff、Hans-Georg Stammler、Beate Neumann

  DOI：10.1021/om100352c

  日期：2010.11.8

  Gas-phase He 1 photoelectron spectra of a series of 2-arylethynyl-1,3,2-benzodiazaboroles BEP-X [1 (X = H), 2 (X = Me), 3 (X = OMe), 4 (X = SMe), 5 (X = NMe2), 6 (X = Br)] have been recorded and assessed by density functional theory calculations. The first ionization energies of these benzodiazaboroles are in the order 5 (7.0 eV) < 3 (7.15 eV) < 2 (7.2 eV) < 1 = 4 = 6 (7.3 eV). As an important result of this study it was disclosed that in contrast to the remaining diazaboroles the frontier orbitals of the amino derivative 5 lack contributions from the diazaborole part of the molecule. In keeping with this, the dipole moment of the ground state (5.51 D) is only slightly changed, to 6.60 D, upon electronic excitation. This also rationalizes the low Stokes shift of 2600 cm(-1) in comparison to the other diazaboroles in this study (5900-7300 cm(-1)).