B,N-dimethyl-1,2-B,N-1,4-cyclohexadiene | 545386-64-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: B,N-dimethyl-1,2-B,N-1,4-cyclohexadiene
• 英文别名: 1,2-Dimethyl-3,6-dihydroazaborinine
• CAS: 545386-64-9
• 化学式: C₆H₁₂BN
• 分子量: 108.979
• InChiKey: HHVJHFSUJKQEPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  B,N-dimethyl-1,2-B,N-1,4-cyclohexadiene 在 氢气 、 钯 作用下， 以 neat (no solvent) 为溶剂， 22.0 ℃ 、3.45 MPa 条件下， 反应 23.0h， 以86%的产率得到B,N-dimethyl-1,2-B,N-cyclohexene
  参考文献：
  名称：

  BN-环己烯衍生物释放-CH2CH2-氢的动力学

  摘要：

  Complete -CH2CH2- dehydrogenation of 1,2-dimethyl-1,2-BN-cyclohexene (1) was achieved using a Pd/C catalyst in a gas-phase microreactor. Arrhenius analysis yielded an activation energy (E-a) of 10.3 +/- 0.3 kcal mol(-1) and a pre-exponential factor (A) of 2.2 +/- 0.2 (log A), respectively. These terms reflect a lesser kinetic favorability in comparison to those determined for all-carbon dimethylcyclohexene (E-a = 8.6 +/- 0.3 kcal mol(-1), log A = 3.6 +/- 0.1). Despite being isostructural and isoelectronic with a C=C bond, the B-N bond of 1 thus appears to confer a different measure of activity with respect to Pd-catalyzed -CH2CH2- dehydrogenation.

  DOI：

  10.1021/acs.organomet.6b00412
• 作为产物：
  描述：

  B,N-diallyl-B-isopropoxy-N-methylaminoborane 在 Grubbs catalyst first generation 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 B,N-dimethyl-1,2-B,N-1,4-cyclohexadiene
  参考文献：
  名称：

  BN-环己烯衍生物释放-CH2CH2-氢的动力学

  摘要：

  Complete -CH2CH2- dehydrogenation of 1,2-dimethyl-1,2-BN-cyclohexene (1) was achieved using a Pd/C catalyst in a gas-phase microreactor. Arrhenius analysis yielded an activation energy (E-a) of 10.3 +/- 0.3 kcal mol(-1) and a pre-exponential factor (A) of 2.2 +/- 0.2 (log A), respectively. These terms reflect a lesser kinetic favorability in comparison to those determined for all-carbon dimethylcyclohexene (E-a = 8.6 +/- 0.3 kcal mol(-1), log A = 3.6 +/- 0.1). Despite being isostructural and isoelectronic with a C=C bond, the B-N bond of 1 thus appears to confer a different measure of activity with respect to Pd-catalyzed -CH2CH2- dehydrogenation.

  DOI：

  10.1021/acs.organomet.6b00412