1-(4-cyanophenyl)-1,2-dicarba-closo-dodecaborane | 147397-98-6

• 英文名称: 1-(4-cyanophenyl)-1,2-dicarba-closo-dodecaborane
• CAS: 147397-98-6
• 化学式: C₉H₁₅B₁₀N
• 分子量: 245.335
• InChiKey: BWDSFXCAJLIKOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  1-(4-cyanophenyl)-1,2-dicarba-closo-dodecaborane 、 对氟硝基苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以51%的产率得到1-(4-cyanophenyl)-2-(4-nitrophenyl)-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Design and synthesis of nonsteroidal progesterone receptor antagonists based on C,C′-diphenylcarborane scaffold as a hydrophobic pharmacophore

  摘要：

  The progesterone receptor (PR) plays important roles in multiple physiological processes, including female reproduction. Here, we report the synthesis of nonsteroidal PR antagonists containing a boron cluster as the hydrophobic core. We found that 1,7-diphenyl-meta-carborane was the preferred substructure among the three carborane isomers. Compound 39 was the most potent PR antagonist (IC50: 29 nM). Compound 41 also exhibited potent activity (IC50: 93 nM), and did not bind to androgen receptor, glucocorticoid receptor or mineralocorticoid receptor. These compounds may be useful for investigating potential clinical applications of PR modulators.

  DOI：

  10.1016/j.ejmech.2014.07.034
• 作为产物：
  描述：

  6,9-(MeCN)2B10H12 、 4-乙炔基苯甲腈 以 甲苯 为溶剂， 以30%的产率得到1-(4-cyanophenyl)-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Labelling of Carbaboranyl Compounds with a Selenium Atom with a View to Applications in Boron-Neutron-Capture Therapy (BNCT) and Positron-Emission Tomography (PET)

  摘要：

  We synthesized 2'-carbaboranyl-2,5'-bi-1H-benzimidazoles containing 10 B-atoms and labeled with Se or the positron-emitting radionuclide Se-73 (t(1/2) = 7.1 h), with a view to their application to cancel. treatment by boron-neutron-capture therapy (BNCT) and to compound-distribution measurements in vivo by positron-emission tomography (PET). Thus, 2,2'-{[2'-(4-[1,2-dicarba-closo-dodecaboran(12)-2-ylmethoxy]phenyl]-[2,5'-bi-1H-benzimidazol]-5-yl}imino)bis[ethanol] (26c) was obtained by the reaction of 2,2'-[(3,4-diaminephenyl)imino]bis[ethanol] (19) with ethyl 2-{4-[1,2-dicarba-closo-dodecaboran(12)-2-ylmethoxy]phenyl}-1H-benzimidazole-5-carboximidate hydrochloride (25), as well as the analogues 26a and 26b (Scheme 6). Tosylation of compound 26c gave 4 regioisomers 27a-d, which, after selenation, produced 2'-{4-[1,2-dicarba-closo-dodecaboran(12)-2-ylmethoxy]phenyl}-5-(tetrahydro-2H-1,4-selenazin-4-yl)-2,5'-bi-1H-benzimidazole (29) in 42% yield (Scheme 7).

  DOI：

  10.1002/1522-2675(20001108)83:11<2926::aid-hlca2926>3.0.co;2-6

文献信息

• Light-promoted copper-catalyzed cage C-arylation of <i>o</i>-carboranes: facile synthesis of 1-aryl-<i>o</i>-carboranes and <i>o</i>-carborane-fused cyclics
  作者：Hangcheng Ni、Zhenpin Lu、Zuowei Xie

  DOI：10.1039/d0nj02029j

  日期：——

  Light-promoted, copper catalyzed cage C–H arylation of o-carboranes with aryl halides has been achieved, leading to the facile synthesis of a variety of 1-aryl-o-carboranes and o-carborane-fused cyclics. This method has the following features: (1) using o-carboranes instead of prefunctionalized iodocarboranes as starting materials; (2) employing earth abundant copper as a catalyst; and (3) room-temperature

  已经实现了光促进的，铜催化的邻氨基甲酸酯与芳基卤化物的笼型CH–H芳基化反应，从而轻松合成了各种1-芳基邻氨基甲酸酯和邻氨基甲烷稠合的环状物。该方法具有以下特点：（1）使用邻氨基甲酸酯代替预官能化的碘代氨基甲酸酯作为起始原料；（2）采用富土铜作为催化剂；（3）室温反应。对照实验表明该反应通过Cu催化的自由基偶联进行。
• Conductance of <i>o</i>-carborane-based wires with different substitution patterns
  作者：Shi-Nuo Xu、Yan Zheng、Jing-Yao Ye、Zhong-Yang Chen、Jian-Feng Yan、Yan-Hou Geng、Wenjing Hong、Yao-Feng Yuan

  DOI：10.1039/d3dt00011g

  日期：——

  Interestingly, the three-dimensional structure in o-carborane-based wires can effectively promote the through-space transmission paths or the formation of stable molecular junctions compared to the corresponding phenyl-centered wires. Moreover, the significant conductance difference of o-carborane-based wires was due to the combination of multiple conduction channels and quantum interference. Understanding

  在这里，我们报告了具有多个传导通道的三种基于邻碳硼烷的分子线（邻-、间-和对-CN）的合成、结构和单分子电导。使用扫描隧道显微镜断裂结 (STM-BJ) 技术和理论计算研究了目标线与相应的以苯基为中心的线相比连通性的影响。有趣的是，与相应的以苯基为中心的导线相比，邻碳硼烷导线的三维结构可以有效促进空间传输路径或稳定分子连接的形成。此外， o的显着电导差异-基于碳硼烷的导线是由于多个传导通道和量子干涉的结合。了解不同桥接基团和锚定基团取代模式的影响为设计基于邻碳硼烷的多通道分子线提供了指导。
• B(9)-OH-<i>o</i>-Carboranes: Synthesis, Mechanism, and Property Exploration
  作者：Yan-Na Ma、Huazhan Ren、Yanxuan Wu、Na Li、Feijing Chen、Xuenian Chen

  DOI：10.1021/jacs.2c13570

  日期：——

  Herein, we present a chemically robust and efficient synthesis route for B(9)-OH-o-carboranes by the oxidation of o-carboranes with commercially available 68% HNO3 under the assistance of trifluoromethanesulfonic acid (HOTf) and hexafluoroisopropanol (HFIP). The reaction is highly efficient with a wide scope of carboranes, and the selectivity of B(9)/B(8) is up to 98:2. The success of this transformation

  在此，我们通过在三氟甲磺酸 (HOTf) 和六氟异丙醇 (HFIP) 的协助下使用市售的 68% HNO 3氧化邻碳硼烷，提出了一种化学稳健且高效的 B(9)-OH-o-碳硼烷合成路线. 反应效率高，碳硼烷范围广，B(9)/B(8)的选择性高达98:2。这种转化的成功依赖于 HNO 3的强亲电性和氧化性，通过布朗斯台德酸 HOTf 和溶剂 HFIP 的氢键促进。机理研究表明，邻碳硼烷的氧化涉及 HNO 3的初始亲电攻击到邻碳硼烷的最具负电性的 B(9) 处的氢原子。在这种转化中，B-H键的氢原子是亲核位点，不同于亲电取代反应中硼原子是亲核位点。因此，这是邻碳硼烷在温和条件下的氧化还原反应，其中 N(V) → N(III) 和 H(-I) → H(I)。9-OH- o的衍生化-carborane 进一步检查，carboranyl 基团被成功地引入氨基酸、聚乙二醇、生物素、脱氧尿苷和糖类。毫无