3-(N-benzoylamino)-1,2-dicarba-closo-dodecaborane | 22043-75-0

• 英文名称: 3-(N-benzoylamino)-1,2-dicarba-closo-dodecaborane
• 英文别名: N-(1,2-dicarba-closo-dodecaboran-3-yl)benzamide；3-(NHCOC6H5)-1.2-C2B10H11
• CAS: 22043-75-0
• 化学式: C₉H₁₇B₁₀NO
• 分子量: 263.35
• InChiKey: DRFVCSDFWSIBGA-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：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  3-(N-benzoylamino)-1,2-dicarba-closo-dodecaborane 在 哌啶 作用下， 以 苯 为溶剂， 以98%的产率得到piperidinium-3-benzoylamino-7,8-dicarbaundecaborate
  参考文献：
  名称：

  Cleavage of 3-amino-o-carborane and its' N-derivatives by bases into the 3-amino-7,8-dicarbaundecaborate anion and its N-derivatives

  摘要：

  Cleavage of 3-amino-o-carborane by alcoholic alkali results in preferential elimination of the boron atom from position six of the polyhedron with the formation of a salt of 3-amino-7,8-dicarbaundecaborate and, to a smaller degree, to elimination of the boron bonded to the NH2 group, which leads to formation of a salt of 7,8-dicarbaundecaborate. Cleavage of 3-amino-o-carborane by piperidine is even more regioselective. Cleavage of N-derivatives of 3-amino-9-carborane by alcoholic alkali or piperidine is regiospecific, leading to salts of N-substituted 7,8-dicarbaundecaborates. 3-Ammonium-7,8-dicarbaundecaborate and a number of its N-derivatives were isolated in zwitterion form for the first time.

  DOI：

  10.1007/bf00961367
• 作为产物：
  描述：

  3-amino-1,2-dicarba-closo-dodecacarborane 在 二碳酸二叔丁酯 作用下， 以 叔丁醇 为溶剂， 生成 3-(N-benzoylamino)-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Kasar, Ramesh A.; Knudsen, Giselle M.; Kahl, Stephen B., Inorganic Chemistry, 1999, vol. 38, p. 2936 - 2940

  摘要：

  DOI：

文献信息

• Some reactions of 3-amino-o-carboranes
  作者：L.I. Zakharkin、V.N. Kalinin、V.V. Gedymin、G.S. Dzarasova

  DOI：10.1016/s0022-328x(00)92943-7

  日期：1970.7

  Preparative procedure for obtaining the secondary and tertiary amines of o-carborane [1,2-dicarbadodecaborane(12)] series by lithium aluminum hydride reduction of their acyl derivatives has been worked out.

  制定了通过氢化铝锂还原其酰基衍生物获得邻氨基甲酸酯[1,2-二氨基十二碳杂硼烷（12）]系列仲胺和叔胺的制备方法。
• [3-N₂-o-C₂B₁₀H₁₁][BF₄]: a useful synthon for multiple cage boron functionalizations of o-carborane
  作者：Da Zhao、Zuowei Xie

  DOI：10.1039/c6sc01566b

  日期：——

  A simple and efficient method for selective cage B(3) multiple functionalization of o-carborane is described. Reaction of [3-N2-o-C2B10H11][BF4] with various kinds of nucleophiles gave a very broad spectrum of cage B(3)-substituted o-carborane derivatives, 3-X-o-C2B10H11 (X = OH, SCN, NH2, NO2, N3, CF3, PO(C6H5)2, etc). This reaction may serve as another efficient [18F]-radiolabeling method of carborane

  描述了一种简单有效的邻碳硼烷选择性笼B(3)多官能化方法。 [3-N 2 - o -C 2 B 10 H 11 ][BF 4 ]与各种亲核试剂反应得到非常广谱的笼型B(3)-取代的邻碳硼烷衍生物，3-X- o - C 2 B 10 H 11 (X = OH、SCN、NH 2 、NO 2 、N 3 、CF 3 、PO(C 6 H 5 ) 2等)。该反应可以作为用于正电子发射断层扫描应用的碳硼烷簇的另一种有效的[ 18 F]-放射性标记方法。
• Mechanochemical Iridium(III)-Catalyzed B-Amidation of <i>o</i>-Carboranes with Dioxazolones
  作者：Gi Uk Han、Seohyun Shin、Yonghyeon Baek、Dongwook Kim、Kooyeon Lee、Jeung Gon Kim、Phil Ho Lee

  DOI：10.1021/acs.orglett.1c03336

  日期：2021.11.5

  Mechanochemistry was successfully applied to the functionalization of carboranes. The mechanochemical iridium(III)-catalyzed regioselective B(3)- and B(4)-amidation of unsubstituted o-carboranes with dioxazolones was developed. In addition, the mechanochemical iridium(III)-catalyzed regioselective B(4)-amidation of substituted o-carboranes was demonstrated. Because mechanochemical B-amidation proceeds

  机械化学成功地应用于碳硼烷的功能化。开发了机械化学铱 (III)-催化区域选择性 B(3)-和 B(4)-未取代的o-碳硼烷与二恶唑酮的酰胺化。此外，还证明了机械化学铱 (III) 催化的区域选择性 B(4)-取代邻碳硼烷的酰胺化。由于机械化学 B-酰胺化在没有有机溶剂或外部加热的情况下顺利进行，因此本方法被认为是典型溶剂型反应的可持续且环保的替代品。
• Synthesis of carborane analogues of γ-aminobutanoic acid
  作者：Valentina A. Ol’shevskaya、Rami Ayuob、Zhanna G. Brechko、Pavel V. Petrovskii、Elena G. Kononova、Galina L. Levit、Victor P. Krasnov、Valery N. Charushin、Oleg N. Chupakhin、Valery N. Kalinin

  DOI：10.1016/j.jorganchem.2005.01.056

  日期：2005.6

  preparation of high yields of novel N-protected carborane amino acid derivatives, 3-acylamino-1-carboxymethyl-2-R-o-carboranes (R = H, Me, Ph), is reported. The synthesis starts from readily available 3-amino-o-carboranes and includes the protection of amino group, introduction of carboxymethyl function to the carbon atom of polyhedron via the metallation of carborane CH bond with sodium amide in liquid ammonia

  报道了制备高产率的新型N-保护的碳硼烷氨基酸衍生物，3-酰基氨基-1-羧甲基-2-R- o-碳硼烷（R ＝ H，Me，Ph）的通用方法。合成从容易获得的3-氨基-邻氨基甲酸酯开始，包括氨基的保护，通过碳硼烷CH键与氨基钠在液氨中的金属化将羧甲基官能团引入多面体的碳原子，以及处理相应的钠碳硼烷与溴乙酸钠。在酸性介质中研究了N-酰化碳硼烷氨基酸的脱保护。根据所采用的过程闭合碳-或巢-carborane氨基酸得到。
• Enantioselective Alkenylation of <i>o</i>-Carboranes via Ir-Catalyzed Asymmetric B–H Activation
  作者：Huifang Zhang、Jie Zhang、Zaozao Qiu、Zuowei Xie

  DOI：10.1021/acscatal.3c03997

  日期：2023.11.3

  The intrinsic chirality of three-dimensional carborane derivatives is established by the substitution patterns on the icosahedral cage, which is much less studied than the planar, axial, central, and helical chirality observed in organic synthesis. Based on transition-metal-catalyzed asymmetrical B–H activation methodology, the addition of functional groups can change the symmetrical o-carborane to

  三维碳硼烷衍生物的内在手性是通过二十面体笼上的取代模式建立的，与有机合成中观察到的平面、轴向、中心和螺旋手性相比，其研究要少得多。基于过渡金属催化的不对称B-H活化方法，添加官能团可以将对称的邻碳硼烷转变为手性笼结构。在此，我们报道了3-酰氨基-邻碳硼烷与二芳基乙炔的不对称硼顶点烯基化，以开发邻碳硼烷的笼( S )-B(4)/( R )-B(7)对映选择性。在温和的反应条件下，Ir 催化剂促进的不对称 ( S )-B(4)-H 活化可实现高达 99% ee 的高效率。对映控制模型是根据 DFT 结果提出的，其中手性膦配体在邻碳硼烷的催化对映选择性 B-H 活化中起着至关重要的作用。