9-hexyl-9-borabicyclo[3.3.1]nonane | 42371-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 9-hexyl-9-borabicyclo[3.3.1]nonane
• 英文别名: 9-Borabicyclo[3.3.1]nonane, 9-hexyl-
• CAS: 42371-64-2
• 化学式: C₁₄H₂₇B
• 分子量: 206.179
• InChiKey: AIBWPMAMCLGBRL-UHFFFAOYSA-N

物化性质

• 沸点：
  284.1±7.0 °C(Predicted)
• 密度：
  0.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-hexyl-9-borabicyclo[3.3.1]nonane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium tetrahydroborate 、 三苯胂 、 三溴化磷 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成 9-bromo-2-hexyl-9H-fluorene
  参考文献：
  名称：

  Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

  摘要：

  A series of fluorene-based derivatives was synthesized and evaluated for inhibiting both InhA and Mycobacterium tuberculosis growth. These compounds were inspired by the previously reported Genz-10850 molecule, a good InhA inhibitor, but with a poor activity against M. tuberculosis growth. Structure activity relationships were performed by introducing the following chemical modifications: 1) the piperazine ring; 2) the amide group; 3) the aryl moiety; and 4) the fluorene moiety. Among these new derivatives, one of them was more effective against both the InhA activity and mycobacterial growth, compared to the hit compound. Docking studies were also performed to rationalize activities of these derivatives. Furthermore, we showed for the first time that efflux pump inhibitors potentiated the efficacy of Genz-10850 (GEQ) derivatives against M. tuberculosis growth, demonstrating that these compounds could be substrates of some efflux pumps. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.035
• 作为产物：
  描述：

  9-(1-Ethyl-butyl)-9-bora-bicyclo[3.3.1]nonane 生成 9-hexyl-9-borabicyclo[3.3.1]nonane
  参考文献：
  名称：

  BROWN, H, C.;RACHERLA, U. S.;TANIGUCHI, H., J. ORG. CHEM., 1981, 46, N 3, 4313-4314

  摘要：

  DOI：
• 作为试剂：
  描述：

  (±)-allyl 3-(3-oxobutyl)-3H-indole-3-carboxylate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 (R,R)-ANDEN-phenyl Trost ligand 、 9-hexyl-9-borabicyclo[3.3.1]nonane 作用下， 以 四氢呋喃 为溶剂， 反应 16.03h， 以65%的产率得到
  参考文献：
  名称：

  烯丙基 Indolenin-3-carboxylates 的催化对映聚合脱羧烯丙基烷基化

  摘要：

  已经开发了一种催化对映聚合工艺，用于将外消旋烯丙基 indolenin-3-carboxylates 转化为对映体富集的 C3-quaternary indolenines。Pd 催化的脱羧烯丙基烷基化反应用于外消旋烯丙基 indolenin-3-carboxylates 的立体消融和季碳中心的对映选择性形成。

  DOI：

  10.1002/ejoc.201300515

文献信息

• Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins
  作者：Nathan A. Owston、Gregory C. Fu

  DOI：10.1021/ja105924f

  日期：2010.9.1

  A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with alkylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.

  已开发出一种用于未活化仲烷基亲电试剂的不对称烷基-烷基 Suzuki 反应的方法，特别是外消旋酰化卤代醇与烷基硼烷试剂的交叉偶联。一系列受保护的溴醇，以及受保护的氯醇和同系溴醇，通过衍生自市售组分的催化剂以良好的 ee 偶联。
• Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers
  作者：Lin Guo、Xiangqian Liu、Christoph Baumann、Magnus Rueping

  DOI：10.1002/anie.201607646

  日期：2016.12.5

  A nickel‐catalyzed alkylation of polycyclic aromatic methyl ethers as well as methyl enol ethers with B‐alkyl 9‐BBN and trialkylborane reagents that involves the cleavage of stable C(sp2)−OMe bonds is described. The transformation has a wide substrate scope and good chemoselectivity profile while proceeding under mild reaction conditions; it provides a versatile way to form C(sp2)−C(sp3) bonds that

  描述了镍催化的多环芳族甲基醚以及甲基烯醇醚与B-烷基9-BBN和三烷基硼烷试剂的反应，涉及到稳定C（sp 2）-OMe键的裂解。该转化具有较宽的底物范围和良好的化学选择性，同时可在温和的反应条件下进行；它提供了一种形成C（sp 2）-C（sp 3）键的通用方法，该方法不会遭受β-氢化物消除。此外，提出了通过裂解惰性C-O键进行的选择性和顺序烷基化过程，以证明该方法的优势。
• Copper-Catalyzed Addition of Alkylboranes to Iminoacetates: Access to α-Alkyl Branched α-Amino Acids
  作者：Xinsheng Xiao、Wei Zhang、Xiaoxia Lu、Yuanfu Deng、Huangfeng Jiang、Wei Zeng

  DOI：10.1002/adsc.201600248

  日期：2016.7.28

  A copper(I)‐catalyzed addition of alkylborane reagents to α‐iminoacetates has been developed to assemble both acyclic and cyclic α‐branched α‐amino carboxylic acid derivatives in good yields. A wide variety of unactivated alkenes are well tolerated in this transformation.

  已开发出一种铜（I）催化的烷基硼烷试剂加到α-亚氨基乙酸酯中的方法，以高产率组装无环和环状α-支链α-氨基羧酸衍生物。在这种转化中，多种未活化的烯烃具有良好的耐受性。
• Highly Active Palladium Catalysts for Suzuki Coupling Reactions
  作者：John P. Wolfe、Robert A. Singer、Bryant H. Yang、Stephen L. Buchwald

  DOI：10.1021/ja992130h

  日期：1999.10.1

  room-temperature Suzuki coupling of aryl bromides and aryl chlorides with 0.5−1.0 mol % Pd. Use of o-(dicyclohexylphosphino)biphenyl (2) allows Suzuki couplings to be carried out at low catalyst loadings (0.000001−0.02 mol % Pd). The process tolerates a broad range of functional groups and substrate combinations including the use of sterically hindered substrates. This is the most active catalyst system in

  乙酸钯和邻（二叔丁基膦）联苯 (4) 的混合物催化芳基溴和芳基氯与 0.5-1.0 mol% Pd 的室温 Suzuki 偶联。使用邻（二环己基膦基）联苯 (2) 允许在低催化剂负载（0.000001-0.02 mol% Pd）下进行 Suzuki 偶联。该工艺可以容忍广泛的官能团和底物组合，包括使用空间位阻底物。这是迄今为止已报道的在反应温度、转换数和空间耐受性方面最活跃的催化剂体系。
• Pd-Mediated C-C and C-S Bond Formation on Solid Support: A Scope and Limitations Study
  作者：Sebastian Wendeborn、Sabine Berteina、Wolfgang K.-D. Brill、Alain De Mesmaeker

  DOI：10.1055/s-1998-22661

  日期：1998.6

  The scope and limitations of Pd(0)-mediated coupling reactions between aromatic halides linked to a polystyrene resin and boronic acid derivatives (Suzuki coupling), aromatic and vinylic tin compounds (Stille coupling), as well as thiols are reported. For all reactions, conditions were optimized and evaluated with various reagents. In many cases, upon cleavage from the solid support, products were obtained in excellent yields. In most cases, the optimized reaction conditions are superior to those previously reported in the literature.

  本文报道了零价钯催化的芳基卤代物与聚苯乙烯树脂相连的配体、硼酸衍生物（铃木偶联反应）、芳基和乙烯基锡化合物（斯蒂尔偶联反应）以及硫醇之间的偶联反应的范围和局限性。针对所有反应，经过优化条件并使用不同试剂进行评估。在许多情况下，从固相载体上切割下来的产物收率极佳。大多数情况下，经过优化的反应条件优于先前文献报道的条件。