1-isopropyl-o-carborane-2-carboxylic acid | 23841-14-7

• 英文名称: 1-isopropyl-o-carborane-2-carboxylic acid
• 英文别名: 1-COOH-2-i-C3H7-1.2-C2B10H10
• CAS: 23841-14-7
• 化学式: C₆H₁₈B₁₀O₂
• 分子量: 230.318
• InChiKey: DXSCXXNSDVRTHR-UHFFFAOYSA-N

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：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1-isopropyl-o-carborane-2-carboxylic acid 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 氧气 、 potassium acetate 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以74%的产率得到
  参考文献：
  名称：

  铑催化邻甲硼烷的笼型B-H键与O2或空气的区域选择性羟基化

  摘要：

  描述了以O 2或空气为氧源的邻氨基甲酸酯中笼形B4-H键的铑催化羟基化反应，它是一种用于区域选择性生成一系列4-OH- o-碳氮烷的新方法在一个锅的过程中。使用O 2或空气作为氧化剂和氧气源使该协议非常环保且实用。

  DOI：

  10.1002/anie.201605880

文献信息

• Iridium(III)-Catalyzed Selective Sulfonamidation of<i>o</i>-Carborane with Sulfonyl Azide by Carboxylic Acid-Assisted B(4)-H Bond Activation
  作者：Huanhuan Li、Fan Bai、Hong Yan、Changsheng Lu、Vladimir I. Bregadze

  DOI：10.1002/ejoc.201601537

  日期：2017.3.10

  An IrIII‐catalyzed direct cage B(4)–H bond sulfonamidation with carboxylic acid assistance is reported. This reaction proceeds in the absence of both external oxidants and ligands, and shows high yields and good functional group tolerance. In particular, direct cage B(4)–H bond amination was achieved by using aryl and aliphatic azides as nitrenoid sources for the first time.

  据报道，在羧酸的辅助下，Ir III催化的直接笼状B（4）-H键磺酰胺化反应。该反应在不存在外部氧化剂和配体的情况下进行，并且显示出高产率和良好的官能团耐受性。特别是，首次通过使用芳基和脂肪族叠氮化物作为类固醇源来实现直接笼状B（4）-H键胺化。
• Transition Metal Catalyzed Direct Amination of the Cage B(4)–H Bond in <i>o</i>-Carboranes: Synthesis of Tertiary, Secondary, and Primary <i>o</i>-Carboranyl Amines
  作者：Hairong Lyu、Yangjian Quan、Zuowei Xie

  DOI：10.1021/jacs.6b07086

  日期：2016.10.5

  catalyzed regioselective amination of the cage B(4)-H bond in o-carboranes has been achieved for the first time using O-benzoyl hydroxylamines or organic azides as the amination reagents, leading to the preparation of a series of tertiary and secondary carboranyl amines. Both amination reactions proceeded under mild conditions without the addition of any external oxidants. Hydrogenolysis of the resultant

  使用邻苯甲酰羟胺或有机叠氮化物作为胺化试剂，首次实现了过渡金属催化的邻碳硼烷中笼型 B(4)-H 键的区域选择性胺化，从而制备了一系列叔、仲羰基胺。两种胺化反应均在温和条件下进行，无需添加任何外部氧化剂。所得产物4-N(CH2Ph)2-o-碳硼烷的氢解以定量产率提供伯碳硼烷胺，4-氨基-o-碳硼烷。
• Synthesis ofo-andm-carborane derivatives of [2,2]paracyclophane and abnormal Clemmensen reduction of ketones of the [2,2]paracyclophane and carborane series
  作者：L. I. Zakharkin、V. A. Ol'shevskaya、L. E. Vinogradova

  DOI：10.1007/bf02496219

  日期：1997.6

  andm-carboranyl substituents in position 4, separated from the [2,2]paracyclophane system by one or two C atoms (alcohols and ketones) were developed. The Clemmensen reduction of a number of ketones of the [2,2]paracyclophane ando-carbonane series occurs abnormally. The reduction of 1-benzoyl-o-carboranes to the corresponding alcohols by zinc in ethanol in a neutral medium was performed for the first

  开发了合成 [2,2] 对环芳烃衍生物的方法，该衍生物在 4 位含有 o-和 m-碳硼烷基取代基，与 [2,2] 对环芳烃系统通过一或两个碳原子（醇和酮）隔开。[2,2] 对环烷和碳烷系列的许多酮的克莱门森还原异常发生。首次在中性介质中在乙醇中用锌将 1-苯甲酰基-o-碳硼烷还原为相应的醇。
• 8-Aminoquinoline as a bidentate traceless directing group for Cu-catalyzed selective B(4,5)–H disulfenylation of <i>o</i>-carboranes
  作者：Yu Chen、Yangjian Quan、Zuowei Xie

  DOI：10.1039/d0cc05207h

  日期：——

  A traceless bidentate directing group guided copper catalyzed cage B(4,5)–H disulfenylation of o-carboranes has been achieved, where the in situ departure of 8-aminoquinoline circumvents additional process for directing group removal.

  一个无痕双齿导向基引导的铜催化笼状B(4,5)-H二硫化反应已经实现，其中8-氨基喹啉的原位离去避免了额外的导向基去除过程。
• Fe-Catalyzed Intramolecular B–H/C–H Dehydrogenative Coupling: Synthesis of Carborane-Fused Nitrogen Heterocycles
  作者：Yu Chen、Hairong Lyu、Yangjian Quan、Zuowei Xie

  DOI：10.1021/acs.orglett.1c01104

  日期：2021.6.4

  We disclose herein the first example of iron-catalyzed regioselective intramolecular C–H/B–H dehydrogenative coupling, affording unprecedented C,B-substituted carborane-fused phenanthroline derivatives. The 8-aminoquinoline type auxiliaries not only serve as the bidentate directing groups but also ingeniously become the core part of the final products. The mechanistic hypothesis includes B–H activation

  我们在此公开了铁催化的区域选择性分子内 C-H/B-H 脱氢偶联的第一个例子，提供了前所未有的 C,B 取代的碳硼烷稠合菲咯啉衍生物。8-氨基喹啉类助剂不仅作为双齿导向基团，而且巧妙地成为最终产品的核心部分。机制假设包括 B-H 激活、反式效应促进的指导基团旋转、C-H 激活和还原消除。