11-(tert-butyl)-5-chloro-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium | 596093-89-9

• 英文名称: 11-(tert-butyl)-5-chloro-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium
• 英文别名: 12-chloro-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azabismocine
• CAS: 596093-89-9
• 化学式: C₁₈H₂₁BiClN
• 分子量: 495.805
• InChiKey: DVEMSXAHKFTVNK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  11-(tert-butyl)-5-chloro-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium 以 乙醚 、 环己烷 为溶剂， 生成 11-(tert-butyl)-5-iodo-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium
  参考文献：
  名称：

  Synthesis and structure of 5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocines

  摘要：

  Hypervalent organobismuth compounds, 6-tert-butyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocines, with 13 different substituents on the bismuth atom including halogens, alkyl, alkenyl, alkynyl, aryl, or phenylthio groups have been synthesized. A key compound, 12-chloro-6-tert-butyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocine, which is a precursor for other azabismocines, has been synthesized by two different procedures; one is based on Akiba's method using 2-bromobenzylbromide as one of the starting materials and the other is a newly developed one using a cheaper starting material, 2-chlorobenzyl chloride. The structures of 12 new bismuth compounds were determined by X-ray diffraction. The eight-membered tetrahydroazabismocine ring has proved to be highly flexible and the hypervalent Bi-N bond distances vary ranging from 2.568(3) to 2.896(5) Angstrom, depending on the electronic nature of the substituents on the bismuth atom. The Bi-N bond distances have good linear relationship against Hammett's sigma(m) constants. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.06.041
• 作为产物：
  描述：

  氯化铋 、 (t)Bu(2-ClC6H4CH2)2N 在 iron(II) chloride Mg 、 I₂ 、 EtMgCl 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到11-(tert-butyl)-5-chloro-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium
  参考文献：
  名称：

  Synthesis and structure of 5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocines

  摘要：

  Hypervalent organobismuth compounds, 6-tert-butyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocines, with 13 different substituents on the bismuth atom including halogens, alkyl, alkenyl, alkynyl, aryl, or phenylthio groups have been synthesized. A key compound, 12-chloro-6-tert-butyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocine, which is a precursor for other azabismocines, has been synthesized by two different procedures; one is based on Akiba's method using 2-bromobenzylbromide as one of the starting materials and the other is a newly developed one using a cheaper starting material, 2-chlorobenzyl chloride. The structures of 12 new bismuth compounds were determined by X-ray diffraction. The eight-membered tetrahydroazabismocine ring has proved to be highly flexible and the hypervalent Bi-N bond distances vary ranging from 2.568(3) to 2.896(5) Angstrom, depending on the electronic nature of the substituents on the bismuth atom. The Bi-N bond distances have good linear relationship against Hammett's sigma(m) constants. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.06.041
• 作为试剂：
  描述：

  4-(吡咯啉基羰基)溴苯 在 silver hexafluoroantimonate 、 1,1,3,3-四甲基二硅氧烷 、 11-(tert-butyl)-5-chloro-5,10,11,12-tetrahydro-5l5-benzo[c]benzo[3,4][1,2]azabismolo[1,2-a][1,2]azabismol-11-ium 作用下， 以 乙腈 为溶剂， 生成 1-(4-溴苯甲基)吡咯烷
  参考文献：
  名称：

  铋催化酰胺还原

  摘要：

  我们报告了一种使用具有三齿配体框架的阳离子 Bi III催化剂与简单且廉价的硅烷作为还原剂将酰胺还原为胺的方案。可还原多种酰胺，可耐受多种官能团。动力学分析和建模用于阐明每个组分的顺序并生成与观察到的实验数据一致的动力学模型。

  DOI：

  10.1002/anie.202306447

文献信息

• Oxidative addition of Bi–C bonds to Pt(0): reaction of Pt(PEt₃)₃ with cyclic organobismuth compounds
  作者：Shigeru Shimada、Xiang-Bo Wang、Masato Tanaka

  DOI：10.1039/d0cc07408j

  日期：——

  The reaction of cyclic organobismuth compounds, 12-phenyl- and 12-chloro-5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocines, with Pt(PEt3)3 was examined. Oxidative addition of the exocyclic Bi–C bond to Pt(0) selectively took place in the reaction of the 12-phenyl derivative. Oxidative addition of the exocyclic Bi–Cl bond reversibly took place and was kinetically preferred, while endocyclic Bi–C bond

  考察了环状有机铋化合物，12-苯基和12-氯-5,6,7,12-四氢二苯并[ c，f ] [1,5]氮杂双胍与Pt（PEt 3）3的反应。在12-苯基衍生物的反应中，有选择地将环外Bi-C键氧化加至Pt（0）。环外Bi-Cl键的氧化加成反应是可逆的，在动力学上是优选的，而环内Bi-C键的氧化加成产物在热力学上受到青睐，并成为12-氯衍生物反应的最终产物。这些结果首次证明了Bi-C键向过渡金属络合物的氧化加成。
• Facile synthesis and antifungal evaluation of hypervalent organoantimony(iii) and organobismuth(iii) thioates with tridentate C,N,C-coordinating ligands
  作者：Zixiu Wang、Yan Huang、Dandan Deng、Shan Li、Yimei Yu、Yifei Ye、Yi Chen、Jian Lei

  DOI：10.1039/d4ob00702f

  日期：——

  In the present work, a series of organometallic thioates bearing a 5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine or -azabismocine framework were synthesized through the cross-coupling reactions of the corresponding halide precursors with thiols and disulfides at room temperature. The former transformation can be achieved under additive-free conditions, and mild dithiothreitol (DTT) is the only additive

  在本工作中，通过相应卤化物前体与 5,6,7,12-四氢二苯并[ c , f ][1,5]氮杂替博辛或-氮杂双胺骨架的交叉偶联反应合成了一系列带有 5,6,7,12-四氢二苯并[c,f][1,5]氮杂替博辛或-氮杂双胺骨架的有机金属硫酸盐。室温下的硫醇和二硫化物。前者的转化可以在无添加剂的条件下实现，而温和的二硫苏糖醇（DTT）是后者中唯一的添加剂。两种方法均具有操作简单、底物范围广、反应收率好的特点。抗真菌试验表明，合成的硫代有机铋( III )对白色念珠菌的抗菌活性明显高于临床氟康唑，而磺化锑产品的抑制作用低至可忽略不计。此外，还发现了此类含 Bi-S 键化合物的抗生物膜潜力。
• Efficient Fixation of Carbon Dioxide by Hypervalent Organobismuth Oxide, Hydroxide, and Alkoxide
  作者：Shuang-Feng Yin、Junpei Maruyama、Takashi Yamashita、Shigeru Shimada

  DOI：10.1002/anie.200802277

  日期：2008.8.18