1,1’-(ethyne-1,2-diyl)-bis(N,N,N’,N’-tetramethylboranediamine) | 1418023-34-3

• 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: 1,1’-(ethyne-1,2-diyl)-bis(N,N,N’,N’-tetramethylboranediamine)
• 英文别名: bis{bis(dimethylamino)boryl}ethyne；N-[2-[bis(dimethylamino)boranyl]ethynyl-(dimethylamino)boranyl]-N-methylmethanamine
• CAS: 1418023-34-3
• 化学式: C₁₀H₂₄B₂N₄
• 分子量: 221.949
• InChiKey: ZVFAIZOPPWCZTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.71
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  13
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(OC)₅Cr=B=N(SiMe₃)₂] 、 1,1’-(ethyne-1,2-diyl)-bis(N,N,N’,N’-tetramethylboranediamine) 以 正己烷 为溶剂， 反应 12.0h， 以65%的产率得到2,3-bis[bis(dimethylamino)boranyl]-N,N-bis(trimethylsilyl)boriren-1-amine
  参考文献：
  名称：

  Electronic and Structural Effects of Stepwise Borylation and Quaternization on Borirene Aromaticity

  摘要：

  Room-temperature photolysis of the amino-boryl complex [(OC)(5)Cr=B=N(SiMe3)(2)] in the presence of a series of mono- or bis(boryl) alkynes bis{bis-(dimethylamino)boryl}ethyne, 1-phenyl-2-bis-(dimethylamino)borylethyne, and 1-trimethylsilyl-2-bis-(dimethylamino)borylethyne led to the isolation of hitherto unknown borylborirenes in resonable yields, that is, [(RC=CR')(mu-BN(SiMe3)(2))] (7, R = B(NMe2)(2), R' = Ph; 8, R = R' = B(NMe2)(2); 9, R = B(NMe2)(2), R' = SiMe3). The borirenes were isolated and spectroscopically characterized by multinuclear NMR, IR, and UV/vis spectroscopy, crystallography, and elemental analysis. Reactivity studies of the borirenes demonstrated their behavior toward different Lewis bases. The isolated adducts and the parent borirenes were compared to 1,3-mesityl-2-phenylborirene and its adducts. To gain insight into the electronic structure and to evaluate the influence of the exocyclic groups, Density Functional Theory (DFT) calculations were carried out.

  DOI：

  10.1021/ja3110126
• 作为产物：
  描述：

  acetylene-bis-magnesium bromide 、 二(二甲氨基)氯化硼 以 四氢呋喃 为溶剂， 反应 48.0h， 以99%的产率得到1,1’-(ethyne-1,2-diyl)-bis(N,N,N’,N’-tetramethylboranediamine)
  参考文献：
  名称：

  Electronic and Structural Effects of Stepwise Borylation and Quaternization on Borirene Aromaticity

  摘要：

  Room-temperature photolysis of the amino-boryl complex [(OC)(5)Cr=B=N(SiMe3)(2)] in the presence of a series of mono- or bis(boryl) alkynes bis{bis-(dimethylamino)boryl}ethyne, 1-phenyl-2-bis-(dimethylamino)borylethyne, and 1-trimethylsilyl-2-bis-(dimethylamino)borylethyne led to the isolation of hitherto unknown borylborirenes in resonable yields, that is, [(RC=CR')(mu-BN(SiMe3)(2))] (7, R = B(NMe2)(2), R' = Ph; 8, R = R' = B(NMe2)(2); 9, R = B(NMe2)(2), R' = SiMe3). The borirenes were isolated and spectroscopically characterized by multinuclear NMR, IR, and UV/vis spectroscopy, crystallography, and elemental analysis. Reactivity studies of the borirenes demonstrated their behavior toward different Lewis bases. The isolated adducts and the parent borirenes were compared to 1,3-mesityl-2-phenylborirene and its adducts. To gain insight into the electronic structure and to evaluate the influence of the exocyclic groups, Density Functional Theory (DFT) calculations were carried out.

  DOI：

  10.1021/ja3110126

文献信息

• Boron-Metallated Borirenes and Bis(Borirenes)
  作者：Holger Braunschweig、Mehmet Ali Celik、Rian D. Dewhurst、Katharina Ferkinghoff、Krzysztof Radacki、Felix Weißenberger

  DOI：10.1002/chem.201600651

  日期：2016.6.13

  metalloborylene complex [(η5‐C5Me5)Fe(CO)2}(μ‐B)Cr(CO)5}] with alkynes and diynes leads to the formation of B‐metallated borirenes and a bis(B‐metallated borirene) through formal transfer of the metalloborylene moiety [(η5‐C5Me5)(OC)2Fe(B:)]. By using this protocol, a range of B‐metallated borirenes with electron‐donating and electron‐withdrawing substituents are prepared, and these are studied spectroscopically

  加热metalloborylene络合物[（η 5 -C 5我5）的Fe（CO）2 }（μ-B）的Cr（CO）5 }]与炔烃和二炔导致B-金属化borirenes和双的形成（B-金属化borirene）通过metalloborylene部分[（η的正式移交5 -C 5我5）（OC）2的Fe（B :)]。通过使用该协议，可以制备一系列带有给电子和吸电子取代基的B金属化硼硼烷，并在光谱，结构和计算上进行研究。配合物的桔黄色还通过与时间有关的密度泛函理论计算进行了解释。