3-(N-acylamino)-o-carborane | 20671-28-7

• 英文名称: 3-(N-acylamino)-o-carborane
• 英文别名: 3-acetylamino-o-carborane
• CAS: 20671-28-7
• 化学式: C₄H₁₅B₁₀NO
• 分子量: 201.279
• InChiKey: XIRYLJOZQFZJLF-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：
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• 环数：
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• 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：

  3-(N-acylamino)-o-carborane 在 哌啶 作用下， 以 苯 为溶剂， 以60%的产率得到piperidinium 3-acetylamino-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 、 乙酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以87%的产率得到3-(N-acylamino)-o-carborane
  参考文献：
  名称：

  Catalytic Regioselective Cage B(8)–H Arylation of o-Carboranes via “Cage-Walking” Strategy

  摘要：

  A proof-of-concept example of catalytic regioselective cage B(8)-H functionalization of o-carboranes has been disclosed for the first time. Under the help of an acylamino directing group at cage B(3), a series of B(8)-arylated, B(4,7,8)-triarylated and B(4,7,8)-trifluorinated o-carborane derivatives were conveniently prepared. On the basis of isolation of a key intermediate, deuterium labeling experiments and DFT calculations, a reaction mechanism involving a high-valent palladium induced "cage-walking" from B(4) to B(8) vertex is proposed to account for the regioselective B(8)-H activation.

  DOI：

  10.1021/jacs.9b00302

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。
• Visible-Light-Promoted Photocatalytic B−C Coupling via a Boron-Centered Carboranyl Radical: Facile Synthesis of B(3)-Arylated<i>o</i>-Carboranes
  作者：Da Zhao、Zuowei Xie

  DOI：10.1002/anie.201511251

  日期：2016.2.24

  A visible‐light‐mediated in situ generation of a boron‐centered carboranyl radical (o‐C2B10H11.) has been described. With eosin Y as a photoredox catalyst, 3‐diazonium‐o‐carborane tetrafluoroborate [3‐N2‐o‐C2B10H11][BF4] was converted into the corresponding boron‐centered carboranyl radical intermediate, which can undergo efficient electrophilic substitution reaction with a wide range of (hetero)arenes

  可见光介导的原位生成硼为中心的碳硼烷基自由基（ø -C 2乙10 ħ 11 。）进行了说明。用曙红Y作为photoredox催化剂，3- diazonium- ö -carborane四氟硼酸盐[3-N 2 - ö -C 2乙10 ħ 11 ] [BF 4 ]转化为相应的以硼为中心碳硼烷基自由基中间体，其可以进行范围广泛的（杂）芳烃的高效亲电取代反应。该通用且简单的步骤为合成3-（杂）芳基化o化合物提供了一种无金属的替代方法碳素。
• [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。
• 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。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.12, 5.1.8, page 202 - 203
  作者：

  DOI：——

  日期：——