diazabicyclo[2.2.2]octane-borane | 15531-40-5

• 英文名称: diazabicyclo[2.2.2]octane-borane
• 英文别名: triethylene diamine monoborane；(DABCO)BH3
• CAS: 15531-40-5
• 化学式: C₆H₁₅BN₂
• 分子量: 126.01
• InChiKey: UQSAWIKXGVMIEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  diazabicyclo[2.2.2]octane-borane 以 neat (no solvent) 为溶剂， 生成 三乙烯二胺 、 1,4-diaazabicyclo[2.2.2]octane diborane (1/2)
  参考文献：
  名称：

  Preparation and Properties of the Mono- and Bisborane Adducts of N,N'-Dimethylpiperazine and Triethylenediamine

  摘要：

  DOI：

  10.1021/ic50045a061
• 作为产物：
  描述：

  1,4-diaazabicyclo[2.2.2]octane diborane (1/2) 在 (CH₃)2NCH₂CH₂N(CH₃)2 作用下， 以 neat (no solvent) 为溶剂， 生成 diazabicyclo[2.2.2]octane-borane
  参考文献：
  名称：

  Preparation and Properties of the Mono- and Bisborane Adducts of N,N'-Dimethylpiperazine and Triethylenediamine

  摘要：

  DOI：

  10.1021/ic50045a061

文献信息

• Coordination Chemistry of Borane in Solution: Application to a STING Agonist
  作者：Alexander Zhdanko、Boris A. Worp、Sébastien Lemaire

  DOI：10.1002/ejoc.202200130

  日期：2022.4.5

  Comparing nitrogen bases having equal steric properties, a linear correlation of BH 3 binding affinity vs. Brønsted acidity was found. This correlation can be used to quickly estimate the BH 3 binding affinity of a substrate if p K a is known. Kinetic studies suggest the ligand exchange to occur as a bimolecular S N 2 reaction unless other nucleophilic species were present in the reaction mixture.

  确定了硼烷配合物与溶液中各种氧、硫、氮和磷亲核试剂的配体交换反应的平衡常数，并建立了一个跨越 12 个数量级的结合亲和力尺度。虽然 K eq 对溶剂的依赖性极小，但配体交换速率差异很大。在 THF 和 CDCl 3 中分别观察到最快和最慢的速率。此外，根据起始复合物的稳定性，配体交换率在非常宽的范围内不同。发现 BH 3 的结合对空间因子比质子化更敏感。比较具有相同空间特性的氮碱基，发现 BH 3 结合亲和力与布朗斯台德酸度的线性相关。如果 p K a 已知，则该相关性可用于快速估计底物的 BH 3 结合亲和力。动力学研究表明，除非反应混合物中存在其他亲核物质，否则配体交换会作为双分子 SN 2 反应发生。
• Liquefaction of Solid-State BH₃NH₃ by Gaseous NH₃
  作者：Liang Gao、Haocheng Fang、Zhenhua Li、Xuebin Yu、Kangnian Fan

  DOI：10.1021/ic200373g

  日期：2011.5.16

  This paper reports for the first time that under ammonia atmosphere, ammonia borane (AB) reversibly absorbs up to at least 6 equiv of NH3, forming liquid AB(NH3)(n) (n = 1-6) complexes at 0 degrees C. Reasonable structures for AB(NH3)(n) were identified via density functional theory calculations, which indicate that the strong classical hydrogen bond formed between the lone pair of NH3 and the -NH3 of AB is the driving force for the absorption of ammonia by AB. By use of the van't Hoff equation, the enthalpy change (Delta H) for AB to absorb one NH3 was determined to be -2.24 kcal/mol, which is in good agreement with the theoretical calculations. Other organic amines were screened to further confirm the role of the N lone pair; only 1,4-diazabicyclo [2.2.2]octane (DABCO) formed a stable adduct, which X-ray structural analysis showed was the DABCO-BH3 species. Finally, Raman spectra of AB(NH3)(n) were collected, and its unique spectral features are also discussed.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.14, 3.13.1, page 135 - 142
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• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.14, 3.8.1.1.3, page 88 - 94
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• Caerio, F. F.; Wagner, R. I., Baldwin, R. A.l, Washburn, R. M., J. Org. Chem. 26 (1971) 3549/50
  作者：Caerio, F. F.、Wagner, R. I.

  DOI：——

  日期：——