1-(4-methoxyphenyl)-1,7-dicarba-closo-dodecaborane | 111426-92-7

• 英文名称: 1-(4-methoxyphenyl)-1,7-dicarba-closo-dodecaborane
• 英文别名: 1-(4-methoxyphenyl)-m-carbaborane
• CAS: 111426-92-7
• 化学式: C₉H₁₈B₁₀O
• 分子量: 250.351
• InChiKey: AFOKKSHMOSISIH-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-methoxyphenyl)-1,7-dicarba-closo-dodecaborane 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到1-(4-hydroxyphenyl)-1,7-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Synthesis and biological evaluation of meta-carborane-containing phenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity

  摘要：

  meta-Carboranylphenoxyacetanilides were synthesized by copper catalyzed coupling reaction of meta-carborane and phenyl iodides. The synthesized compounds were evaluated for their ability to inhibit hypoxia-induced HIF-1 transcriptional activity using a cell-based reporter gene assay. Among the compounds synthesized, meta-carborane containing phenoxyanilides 2d and 2h, which have an isobutyl group on meta-carborane, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity toward HeLa cell-based reporter gene assay with the IC50 values of 0.73 and 0.55 mu M, respectively. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.05.029
• 作为产物：
  描述：

  1,7-dicarba-closo-dodecaborane(12) 、 4-碘苯甲醚 在 正丁基锂 、 吡啶 、 copper(l) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 以71%的产率得到1-(4-methoxyphenyl)-1,7-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Synthesis and biological evaluation of novel m-carborane-containing estrogen receptor partial agonists as SERM candidates

  摘要：

  We designed and synthesized novel m-carborane-containing selective estrogen receptor modulator (SERM) candidates using previously reported m-carborane-containing ER partial agonist 1 as the lead compound. Biological activities were evaluated by means of ER alpha competitive binding assay and MCF-7 cell proliferation assay. Re-positioning the N,N-dimethylaminoethyloxy group at the para position of 1 to the meta position enhanced the ER alpha-binding affinity, and 4c showed the highest relative binding affinity (RBA: 83 vs 17 beta-estradiol = 100) among the tested compounds. Compound 4b showed the most potent ER-agonist activity (EC50: 1.4 nM) and the lowest maximal efficacy (E-max: 50%) in MCF-7 cell proliferation assay. Inhibition of 0.1 nM 17 beta-estradiol-induced MCF-7 cell proliferation by 4b (IC50: 0.4 mu M) was at least 10 times more potent than that of the lead compound 1. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.083

文献信息

• Synthesis of Carboranylated Dihydropyrrolo[1,2-<i>a</i>]quinoxalines and Dihydroindolo[1,2-<i>a</i>]quinoxalines by BF₃·OEt₂-Catalyzed Heterocyclization of <i>C</i>-Formyl-<i>o</i>-carboranes and Investigation of Their Oxidation Stability
  作者：Zhen-Zhen Sun、Pan Gao、Yong Yang、Tao Wang、Xiao-Jun Wu、You-Qing Wang

  DOI：10.1021/acs.joc.3c02443

  日期：2024.3.1

  BF3·OEt2-catalyzed synthesis of carboranylated dihydropyrrolo[1,2-a]quinoxalines and dihydroindolo[1,2-a]quinoxalines in 30–99% yields is presented through the heterocyclization of various C-modified C-formyl-o-carboranes with 1-(2-aminophenyl)-pyrroles/indoles. A systematic comparative investigation of their oxidation stability in air confirmed that 4-carboranyl-4,5-dihydropyrrolo[1,2-a]quinoxaline had better

  通过各种C-修饰的C-甲酰基-的杂环化，BF 3 ·OEt 2催化合成碳硼酰化二氢吡咯并[1,2- a ]喹喔啉和二氢吲哚并[1,2- a ]喹喔啉，产率30-99%邻碳硼烷与1-(2-氨基苯基)-吡咯/吲哚。对它们在空气中氧化稳定性的系统比较研究证实，4-碳硼基-4,5-二氢吡咯并[1,2- a ]喹喔啉比4-苯基类似物具有更好的稳定性。 N-乙酰基取代的碳硼酰化二氢吡咯并[1,2- a ]喹喔啉的笼式脱硼反应产生相应的7,8-硝基-碳硼烷铯盐。还实现了动力学拆分，以获得带有碳硼烷笼碳键合手性立体中心的光学纯碳硼酰化N-杂环支架。
• Kovredov, A. I.; Shaugumbekova, Zh. S.; Kazantsev, V. A., Journal of general chemistry of the USSR, 1986, vol. 56, p. 2045 - 2049
  作者：Kovredov, A. I.、Shaugumbekova, Zh. S.、Kazantsev, V. A.、Zakharkin, L. I.

  DOI：——

  日期：——