2-octyl-1,3,2-benzodiazaborolane | 918897-56-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-octyl-1,3,2-benzodiazaborolane
• 英文别名: 2-Octyl-2,3-dihydro-1H-1,3,2-benzodiazaborole；2-octyl-1,3-dihydro-1,3,2-benzodiazaborole
• CAS: 918897-56-0
• 化学式: C₁₄H₂₃BN₂
• 分子量: 230.161
• InChiKey: TVZVPAAOBVNDFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-octyl-1,3,2-benzodiazaborolane 、 2-溴苯甲醚 在 potassium phosphate monohydrate 、 palladium diacetate 、 三环己基膦 作用下， 反应 0.67h， 以35%的产率得到1-甲氧基-2-辛基苯
  参考文献：
  名称：

  Microwave-assisted Suzuki–Miyaura cross-coupling of 2-alkyl and 2-alkenyl-benzo-1,3,2-diazaborolanes

  摘要：

  Nitrogen-based boronate esters, such as 2-octyl-benzo-1,3,2-diazaborolane, 2-phenethyl-benzo-1,3,2-diazaborolane, and 2-{(1E)-hexenyl}-benzo-1,3,2-diazaborolane have been shown to be suitable coupling partners with arylhalides in microwave accelerated Suzuki cross-coupling reactions. Reaction yields of up to 89% were achieved. The use of a silicon group attached to the nitrogen atom, proved to enhance the reactivity of 2-octyl-benzo-1,3,2-diazaborolane. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.095
• 作为产物：
  描述：

  邻苯二胺 在 Wilkinson's catalyst 、 dimethyl sulfide borane 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 2-octyl-1,3,2-benzodiazaborolane
  参考文献：
  名称：

  Microwave-assisted Suzuki–Miyaura cross-coupling of 2-alkyl and 2-alkenyl-benzo-1,3,2-diazaborolanes

  摘要：

  Nitrogen-based boronate esters, such as 2-octyl-benzo-1,3,2-diazaborolane, 2-phenethyl-benzo-1,3,2-diazaborolane, and 2-{(1E)-hexenyl}-benzo-1,3,2-diazaborolane have been shown to be suitable coupling partners with arylhalides in microwave accelerated Suzuki cross-coupling reactions. Reaction yields of up to 89% were achieved. The use of a silicon group attached to the nitrogen atom, proved to enhance the reactivity of 2-octyl-benzo-1,3,2-diazaborolane. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.095

文献信息

• Rhodium-Catalyzed Hydroboration Reactions with Sulfur and Nitrogen Analogues of Catecholborane
  作者：Siphamandla W. Hadebe、Ross S. Robinson

  DOI：10.1002/ejoc.200600564

  日期：2006.11

  Rhodium-catalyzed hydroboration of 1-octene and trans-4-octene with sulfur- and nitrogen analogues of catecholborane are demonstrated with the use of in situ 11B NMR spectroscopy. Our study shows that the sulfur- and nitrogen analogues are significantly less prone to disproportionation than catechol, which results in enhanced yields of the desired compounds.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  1-辛烯和反式-4-辛烯与儿茶酚硼烷的硫和氮类似物的铑催化硼氢化反应通过使用原位 11B 核磁共振光谱进行了证明。我们的研究表明，硫和氮类似物比邻苯二酚更不容易发生歧化，从而提高所需化合物的产量。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2006）
• Cobalt- and Iron-Catalyzed Isomerization–Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes
  作者：Takahiko Ogawa、Adam J. Ruddy、Orson L. Sydora、Mark Stradiotto、Laura Turculet

  DOI：10.1021/acs.organomet.6b00823

  日期：2017.1.23

  The synthesis and characterization of a series of structurally varied N-phosphinoamidinate-ligated cobalt complexes is described, along with the successful application of these and a related iron complex as precatalysts in the isomerization hydroboration of terminal, geminal, and internal alkenes. These reactions proceed under mild conditions (23-65 degrees C), at relatively low base-metal loadings (1-5 mol %), typically without cosolvent, and with high terminal hydroboration selectivity across a broad spectrum of branched alkenes. With some of the alkene substrates examined, the Nphosphinoamidinate-ligated precatalysts employed herein are shown to provide alternative terminal selectivity versus other previously reported precatalyst classes for such transformations. Reports of terminal-selective metal-catalyzed alkene isomerization hydroboration disclosed thus far in the literature employ pinacolborane (HBPin); while effective in the system herein, we also report the first examples of such transformations employing either 1,3-dimethyl-1,3-diaza-2-boracydopentane or benzo-1,3,2-diazaborolane. The application of these 1,3,2-diazaborolanes in place of HBPin in some instances enables novel terminal selectivity in the isomerization hydroboration of branched alkenes.