15-N,15-N,16-N,16-N-tetramethyl-15,16-diboratetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diamine | 1379114-99-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 15-N,15-N,16-N,16-N-tetramethyl-15,16-diboratetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diamine
• CAS: 1379114-99-4
• 化学式: C₁₈H₂₂B₂N₂
• 分子量: 288.008
• InChiKey: LAHVNVWRMHFEQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  15-N,15-N,16-N,16-N-tetramethyl-15,16-diboratetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diamine 在 盐酸 、 乙醚 作用下， 以 氯仿 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  An inorganic propellane with central B–B bond

  摘要：

  9,10-二氢蒽-9,10-二基桥接的 B2(NMe2)2 很容易在其部分 BN 双键上添加 [H2NMe2]+、HCl 和 F3CCOOH，从而形成单加合物或二加合物；用 1-iso-propyl-2-mercaptoimidazole 处理后会产生三重 BâB 桥接的丙烷样结构。

  DOI：

  10.1039/c2cc32256k
• 作为产物：
  描述：

  9,10-二氢蒽 以 正己烷 、 苯 为溶剂， 反应 108.0h， 生成 15-N,15-N,16-N,16-N-tetramethyl-15,16-diboratetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diamine
  参考文献：
  名称：

  Insertion Reactions into the Boron–Boron Bonds of Barrelene-Type 1,2-Diaminodiboranes(4)

  摘要：

  Double lithiation of 9,10-dihydroanthracene (DHA) or 6,13-dihydropentacene (DHP) with nBuLi, followed by the addition of B-2(NMe2)(2)Cl-2, affords 9,10-DHA-9,10-diyl- (1a) or 6,13-DHP-6,13-diyl-bridged B-2(NMe2)(2) (1p) in good yields. Upon treatment with Pt(PEt3)(3) in C6H6 at 60 degrees C, both compounds cleanly insert a Pt(PEt3)(2) moiety into their B-B bonds to furnish the corresponding diboryl Pt(II) complexes 2a and 2p. Compound 2a reacts with excess tBuCCH to give an equimolar mixture of the B-(tBu)C-C(H)-B-bridged 9,10-DHA 3 and Pt(eta(2)-tBuCCH)(PEt3)(2) (4). The addition of isocyanides to either the Pt(II) complex 2a or the Pt-free species 1a yields bicyclic products, in which a 9,10-DHA-9,10-diyl fragment is spanned by a B-C(-NR)-B linker (R = tBu (5), iPr (6)). Both 5 and 6 are extremely prone to hydrolysis. In the case of 6, a water-induced rearrangement reaction leading to a B-C-bridged 9,10-DHA 8 was observed.

  DOI：

  10.1021/om501087u

文献信息

• An inorganic propellane with central B–B bond
  作者：Steffen Pospiech、Sarah Brough、Michael Bolte、Hans-Wolfram Lerner、Holger F. Bettinger、Matthias Wagner

  DOI：10.1039/c2cc32256k

  日期：——

  9,10-Dihydroanthracene-9,10-diyl-bridged B2(NMe2)2 readily adds [H2NMe2]+, HCl and F3CCOOH across its partial BN double bond(s), thereby forming mono- or diadducts; treatment with 1-iso-propyl-2-mercaptoimidazole leads to a triply B–B-bridged propellane-like structure.

  9,10-二氢蒽-9,10-二基桥接的 B2(NMe2)2 很容易在其部分 BN 双键上添加 [H2NMe2]+、HCl 和 F3CCOOH，从而形成单加合物或二加合物；用 1-iso-propyl-2-mercaptoimidazole 处理后会产生三重 BâB 桥接的丙烷样结构。
• Insertion Reactions into the Boron–Boron Bonds of Barrelene-Type 1,2-Diaminodiboranes(4)
  作者：Steffen Pospiech、Michael Bolte、Hans-Wolfram Lerner、Matthias Wagner

  DOI：10.1021/om501087u

  日期：2014.12.8

  Double lithiation of 9,10-dihydroanthracene (DHA) or 6,13-dihydropentacene (DHP) with nBuLi, followed by the addition of B-2(NMe2)(2)Cl-2, affords 9,10-DHA-9,10-diyl- (1a) or 6,13-DHP-6,13-diyl-bridged B-2(NMe2)(2) (1p) in good yields. Upon treatment with Pt(PEt3)(3) in C6H6 at 60 degrees C, both compounds cleanly insert a Pt(PEt3)(2) moiety into their B-B bonds to furnish the corresponding diboryl Pt(II) complexes 2a and 2p. Compound 2a reacts with excess tBuCCH to give an equimolar mixture of the B-(tBu)C-C(H)-B-bridged 9,10-DHA 3 and Pt(eta(2)-tBuCCH)(PEt3)(2) (4). The addition of isocyanides to either the Pt(II) complex 2a or the Pt-free species 1a yields bicyclic products, in which a 9,10-DHA-9,10-diyl fragment is spanned by a B-C(-NR)-B linker (R = tBu (5), iPr (6)). Both 5 and 6 are extremely prone to hydrolysis. In the case of 6, a water-induced rearrangement reaction leading to a B-C-bridged 9,10-DHA 8 was observed.