3-methyl-1,2-dicarba-closo-dodecaborane | 32197-04-9

• 英文名称: 3-methyl-1,2-dicarba-closo-dodecaborane
• 英文别名: 3-methyl-o-carborane；1,2-C2B10H11-3-CH3；3-Me-1,2-closo-C2B10H11；3-Me-1,2-C2B10H11
• CAS: 32197-04-9
• 化学式: C₃H₁₄B₁₀
• 分子量: 158.254
• InChiKey: YTCYTXAHGABMRA-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-methyl-1,2-dicarba-closo-dodecaborane 、 三甲胺盐酸盐 在 KOH 、 HCl 作用下， 以 乙醇 、 水 为溶剂， 以84%的产率得到[NHMe3][3-Me-7,8-nido-C2B9H11]
  参考文献：
  名称：

  Designed Synthesis of New ortho-Carborane Derivatives: from Mono- to Polysubstituted Frameworks

  摘要：

  The use of nucleophilic and electrophilic processes allow the designed synthesis of several B-iodinated derivatives of o-carborane. Because of the straightforward Pd-catalyzed conversion of B-I to B-C bond with Grignard reagents, such as methylMgBr and biPhenylMgBr, both, symmetrical 3,6-R-2-1,2-closo-C2B10H10 and asymmetrical 3-1-6-Me-1,2-closo-C2B10H10 could be obtained. Not only conventional reactions in solution have been studied but also a highly efficient, clean and fast solvent-free procedure has provided successful results to regioselectively produce B-iodinated o-carborane derivatives by a careful control of the reaction conditions. The high number of nonequivalent leaving groups in boron iodinated o-carborane derivatives opens the possibility through B-C coupling to materials with novel possibilities and to self-assembling due to the enhanced polarizability of the C-H bond.

  DOI：

  10.1021/ic800362z
• 作为产物：
  描述：

  1,2-dicarba-closo-dodecaborane(12) 、 甲基二氯硼烷 在 NaOH 、 Na or NaH or butyl lithium 作用下， 生成 3-methyl-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  3- o-碳环烷烃衍生物系列中的Wolff，Beckmann，Hofmann，Curtius和Schmidt重排：1,2-二甲氨基-氯-十二碳烷

  摘要：

  以3-邻-碳硼烷衍生物为例，已经表明，Wolff，Beckmann，Hofmann，Curtius和Schmidt重排通过BC键裂解和富电子的3- o-碳硼烷基迁移至电子缺陷中心进行。的（1-甲基拜尔维利格反应ö -carborane -3-基）苯基酮导致1-甲基-3-迁移ö -carboranyl基。

  DOI：

  10.1016/s0040-4020(01)90882-8

文献信息

• [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。
• Formal Insertion of <i>o</i>-Carborynes into Ferrocenyl C–H Bonds: A Simple Access to <i>o</i>-Carboranylferrocenes
  作者：Sunewang Rixin Wang、Zuowei Xie

  DOI：10.1021/om300324n

  日期：2012.6.25

  [1-(η5-C5H4)(3-R-1,2-C2B10H10)]Fe(η5-C5H5) (R = H, Ph, Me, Cl, Br, and I) in 19–44% isolated yields. On the other hand, in addition to the desired C–H bond insertion products [1-(η5-C5H4)(3-X-1,2-C2B10H10)]Fe(η5-C5H5), bis(ferrocenyl)-o-carboranes 1,2-[(η5-C5H5)Fe(η5-C5H4)]2-3-X-1,2-C2B10H9 were isolated from the reactions of 1-I-2-Li-3-X-1,2-C2B10H9 (X = Cl, Br, and I) in 12%, 15%, and 8% yields, respectively

  的插入ø -carborynes（1,2-脱氢ö -carboranes）二茂铁成C-H键进行了说明，提供的官能化二茂铁的制备方法方便Ò -carboranes。碳炔前体1-I-2-Li-9,12-Me 2 -1,2-C 2 B 10 H 8或1-I-2-Li-3-R-1,2-C 2 B的反应10 ħ 9（R = H，PH，Me中，氯，溴，和I）与在80℃下在环己烷2.5当量的二茂铁，得到[1-（η 5 -C 5 H ^ 4）（9,12-ME 2 -1,2-C 2 B 10 H 9）]的Fe（η 5 -C 5 H ^ 5）和[1-（η 5 -C 5 H ^ 4）（3-R-1,2--C 2乙10 ħ 10）]的Fe（η 5 -C 5 H ^ 5）（R = H，Ph，Me，Cl，Br和I），分离产率为19-44％。在另一方面，除了所期望的C-H键插入产品[1-（η 5 -C 5 H ^ 4）（3-X-1
• 3-o-Carboranylcarbenes
  作者：Ji Li、David J. Caparrelli、Maitland Jones

  DOI：10.1021/ja00055a007

  日期：1993.1

  An investigation of the reactions of three boron-substituted carbenes with alkened and alkanes uncovers substantial triplet reactivity. The triplet reveals itself not through addition or insertion reactions, but by abstraction to give a radical that abstracts again to give, ultimately, methyl-o-carboranes

  对三种硼取代的卡宾与烯烃和烷烃的反应的研究揭示了大量的三线态反应性。三联体不是通过加成或插入反应显示自己，而是通过抽象得到一个自由基，然后再次抽象得到甲基-邻碳硼烷
• Sequential Nucleophilic−Electrophilic Reactions Selectively Produce Isomerically Pure Nona‐ <i>B</i> ‐Substituted <i>o</i> ‐Carborane Derivatives
  作者：Gemma Barberà、Francesc Teixidor、Clara Viñas、Reijo Sillanpää、Raikko Kivekäs

  DOI：10.1002/ejic.200390195

  日期：2003.4

  Nine equal substituents on the intensively studied o-carborane have been obtained for the first time by a combined nucleophilic-electrophilic reaction sequence. Iodine and methyl groups have been introduced to prove the generality of the method. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  通过结合亲核-亲电反应序列，首次在深入研究的邻碳硼烷上获得了九个相等的取代基。已引入碘和甲基以证明该方法的通用性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• <scp>Visible‐Light‐Promoted Palladium‐Catalyzed Cross‐Coupling</scp> of Iodocarboranes with Disulfides and Phenylselenyl Chloride^†
  作者：Shimeng Li、Yizhen Liu、Zuowei Xie

  DOI：10.1002/cjoc.202300481

  日期：2024.1.15

  This work describes a general method for the synthesis of a series of sulfenylated and selenylated carboranes at room temperature using readily available iodocarboranes as starting materials via boron-centered carboranyl radicals. Such hypervalent boron radicals are generated by a visible-light-promoted Pd(0)/Pd(I) pathway. They are useful intermediates and can be trapped by disulfides and phenylselenyl

  这项工作描述了在室温下使用容易获得的碘碳硼烷作为起始原料，通过以硼为中心的碳硼烷基自由基合成一系列磺酰化和硒化碳硼烷的一般方法。这种高价硼自由基是由可见光促进的 Pd(0)/Pd(I) 途径产生的。它们是有用的中间体，可以被二硫化物和苯基硒基氯捕获，以方便构建 B-S/Se 键。