5,11-Diethyl-4,6,10,12-tetramethyl-1,3-diaza-2-boratricyclo[7.3.0.03,7]dodeca-4,6,9,11-tetraene | 1265439-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5,11-Diethyl-4,6,10,12-tetramethyl-1,3-diaza-2-boratricyclo[7.3.0.03,7]dodeca-4,6,9,11-tetraene
• 英文别名: 5,11-diethyl-4,6,10,12-tetramethyl-1,3-diaza-2-boratricyclo[7.3.0.03,7]dodeca-4,6,9,11-tetraene
• CAS: 1265439-74-4
• 化学式: C₁₇H₂₅BN₂
• 分子量: 268.21
• InChiKey: NTCYGLNMANRHQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,11-Diethyl-4,6,10,12-tetramethyl-1,3-diaza-2-boratricyclo[7.3.0.03,7]dodeca-4,6,9,11-tetraene 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Isomeric Dipyrrinato and Dipyrromethanato Boranes

  摘要：

  Reaction of the dipyrrin ligand 1,3,7,9-tetramethyl-2,8-diethyldipyrrin with BH3 center dot SMe2 initially gives a dipyrrin-BH3 adduct, which eliminates dihydrogen to form the dipyrrin-supported BH2 borane (LBH2)-B-H. This species is unstable toward isomerization to its dipyrromethane isomer 1, via a (possibly BH3 catalyzed) hydride transfer from boron to the meso position of the dipyrrin core. Computations suggest that 1 is similar to 4 kcal mol(-1) more stable than the dipyrrin isomer. These conclusions were supported by low-temperature NMR and UV-vis/fluorescence spectroscopic experiments and labeling studies using BD3 center dot SMe2. Borane 1 is susceptible to hydride abstraction to form the previously characterized borenium ion [(LBH)-B-H][B(C6F5)(4)] and takes up hydride to form a dipyrromethane borohydride, which was characterized spectroscopically and crystallographically.

  DOI：

  10.1021/om1011038
• 作为产物：
  描述：

  2,4,8,10-tetramethyl-3,9-diethyldipyrrolyl-5,7-methene 在 dimethyl sulfide borane 作用下， 以 甲苯 为溶剂， 反应 4.25h， 以70%的产率得到5,11-Diethyl-4,6,10,12-tetramethyl-1,3-diaza-2-boratricyclo[7.3.0.03,7]dodeca-4,6,9,11-tetraene
  参考文献：
  名称：

  Isomeric Dipyrrinato and Dipyrromethanato Boranes

  摘要：

  Reaction of the dipyrrin ligand 1,3,7,9-tetramethyl-2,8-diethyldipyrrin with BH3 center dot SMe2 initially gives a dipyrrin-BH3 adduct, which eliminates dihydrogen to form the dipyrrin-supported BH2 borane (LBH2)-B-H. This species is unstable toward isomerization to its dipyrromethane isomer 1, via a (possibly BH3 catalyzed) hydride transfer from boron to the meso position of the dipyrrin core. Computations suggest that 1 is similar to 4 kcal mol(-1) more stable than the dipyrrin isomer. These conclusions were supported by low-temperature NMR and UV-vis/fluorescence spectroscopic experiments and labeling studies using BD3 center dot SMe2. Borane 1 is susceptible to hydride abstraction to form the previously characterized borenium ion [(LBH)-B-H][B(C6F5)(4)] and takes up hydride to form a dipyrromethane borohydride, which was characterized spectroscopically and crystallographically.

  DOI：

  10.1021/om1011038

文献信息

• Isomeric Dipyrrinato and Dipyrromethanato Boranes
  作者：Catherine Bonnier、Warren E. Piers、Masood Parvez.

  DOI：10.1021/om1011038

  日期：2011.3.14

  Reaction of the dipyrrin ligand 1,3,7,9-tetramethyl-2,8-diethyldipyrrin with BH3 center dot SMe2 initially gives a dipyrrin-BH3 adduct, which eliminates dihydrogen to form the dipyrrin-supported BH2 borane (LBH2)-B-H. This species is unstable toward isomerization to its dipyrromethane isomer 1, via a (possibly BH3 catalyzed) hydride transfer from boron to the meso position of the dipyrrin core. Computations suggest that 1 is similar to 4 kcal mol(-1) more stable than the dipyrrin isomer. These conclusions were supported by low-temperature NMR and UV-vis/fluorescence spectroscopic experiments and labeling studies using BD3 center dot SMe2. Borane 1 is susceptible to hydride abstraction to form the previously characterized borenium ion [(LBH)-B-H][B(C6F5)(4)] and takes up hydride to form a dipyrromethane borohydride, which was characterized spectroscopically and crystallographically.