(4-bromophenyl)(4-nitrophenyl)methan-1-ol | 10372-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-bromophenyl)(4-nitrophenyl)methan-1-ol
• 英文别名: (4-bromophenyl)(4-nitrophenyl)methanol；4-Brom-4'-nitro-benzhydrol；4-Nitro-4'-brom-benzhydrol；(4-Bromophenyl)-(4-nitrophenyl)methanol
• CAS: 10372-94-8
• 化学式: C₁₃H₁₀BrNO₃
• 分子量: 308.131
• InChiKey: FXDWZFMHWXUMED-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  470.9±40.0 °C(Predicted)
• 密度：
  1.579±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-bromophenyl)(4-nitrophenyl)methan-1-ol 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (4-溴苯基)(4-硝基苯基)甲酮
  参考文献：
  名称：

  铑催化的对映选择性 B-H 键插入 gem-二芳基卡宾：有效获取 gem-二芳基甲炔硼烷

  摘要：

  我们报告了以二芳基重氮甲烷作为卡宾前体的高对映选择性二铑催化的 B-H 键插入反应。这些反应以高产率（高达 99 % 的产率）、高活性（高达 14 300 的转化率）、高对映选择性（高达 99 % ee）提供了手性 gem-二芳基次甲基硼烷化合物，并显示出前所未有的广泛官能团耐受性。

  DOI：

  10.1002/anie.202109447
• 作为产物：
  描述：

  (4-溴苯基)(4-硝基苯基)甲酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以85%的产率得到(4-bromophenyl)(4-nitrophenyl)methan-1-ol
  参考文献：
  名称：

  Discovery of 1,1′-Biphenyl-4-sulfonamides as a New Class of Potent and Selective Carbonic Anhydrase XIV Inhibitors

  摘要：

  New 1,1'-biphenylsulfonamides were synthesized and evaluated as inhibitors of the ubiquitous human carbonic anhydrase isoforms I, II, IX, XII, and XIV using acetazolamide (AAZ) as reference compound. The sulfonamides 1-21 inhibited all the isoforms, with K-i values in the nanomolar range of concentration, and were superior to AAZ against all of them. X-ray crystallography and molecular modeling studies on the adducts that compound 20, the most potent hCA XIV inhibitor of the series (K-i, = 0.26 nM), formed with the five hCAs, provided insight into the molecular determinants responsible for the high affinity of this molecule toward the target enzymes. The results pave the way to the development of 1.1'-biphenylsulfonamides as a new class of highy potent hCA XIV inhibitors.

  DOI：

  10.1021/acs.jmedchem.5b01144

文献信息

• Copper(II) Acetate-Catalyzed Addition of Arylboronic Acids to Aromatic Aldehydes
  作者：Hanmei Zheng、Qiang Zhang、Jiuxi Chen、Miaochang Liu、Shuanghua Cheng、Jinchang Ding、Huayue Wu、Weike Su

  DOI：10.1021/jo802225j

  日期：2009.1.16

  A novel copper-catalyzed protocol for the synthesis of carbinol derivatives has been developed. In the presence of copper(II) acetate and dppf, carbinol derivatives were prepared by the addition of arylboronic acids to aromatic aldehydes in good to excellent yields. Moreover, the rigorous exclusion of air or moisture is not required in these transformations.

  已经开发了用于合成甲醇衍生物的新颖的铜催化方案。在乙酸铜（II）和dppf的存在下，通过将芳族硼酸加成到芳族醛中来制备甲醇衍生物，收率很好。此外，在这些转换中不需要严格排除空气或湿气。
• Cr³⁺-Mediated Addition of Arylzincs to Aldehydes
  作者：Yoshihiro Ogawa、Mitsuo Mori、Akihiro Saiga、Kentaro Takagi

  DOI：10.1246/cl.1996.1069

  日期：1996.12

  Addition of arylzincs to aldehydes was achieved by making use of the novel transmetallation of arylzincs into Cr3+ compounds. Various α-substituted benzyl alcohols or 3-substituted 1(3H)-isobenzofuranones, containing reactive functional groups, were synthesized in good yields. Me3SiCl exerted beneficial effects on the reaction.

  通过将芳基锌转化为 Cr3+ 化合物的新型转金属化反应，实现了芳基锌对醛的加成。采用多种包含反应性官能团的 α-取代苄醇或 3-取代 1(3H)-异苯并呋喃酮，在良好的产率下被合成。Me3SiCl 对反应产生了有益的影响。
• Nucleophilic Additions of Arylzinc Compounds to Aldehydes Mediated by CrCl₃:  Efficient and Facile Synthesis of Functionalized Benzhydrols, 1(3<i>H</i>)-Isobenzofuranones, Benzyl Alcohols, or Diaryl Ketones
  作者：Yoshihiro Ogawa、Akihiro Saiga、Mitsuo Mori、Takanori Shibata、Kentaro Takagi

  DOI：10.1021/jo991444k

  日期：2000.2.1

  benzhydrols 4a-f in good yields. From arylzinc compounds 1a,b, 3-aryl-1(3H)-isobenzofuranones 3a-f were given by the CrCl(3)-mediated reaction with arylaldehydes 2a-f. Diaryl ketones 5a-e were obtained in good yields by the addition of excess amount of benzaldehyde as an oxidant to the resulting solution after the CrCl(3)-mediated reaction between arylzinc compounds 1c-g and arylaldehydes 2b,g was completed

  在化学计量的CrCl（3）和三甲基氯硅烷（TMSCl）的存在下，芳基锌化合物1c-h向芳基醛2a，b，g的亲核加成反应在室温下平稳进行，以良好的收率得到相应的苯甲醇4a-f。从芳基锌化合物1a，b通过CrCl（3）介导的与芳基醛2a-f的反应得到3-芳基-1（3H）-异苯并呋喃酮3a-f。在芳基锌化合物1c-g与芳基醛2b，g之间完成CrCl（3）介导的反应后，通过向所得溶液中添加过量的苯甲醛作为氧化剂，以高收率获得二芳基酮5a-e。在芳基锌化合物1a，d，f与烷基6b-f的亲核加成中，在添加醛之前，需要用CrCl（3）处理芳基锌化合物，以防止可烯化的醛对芳基锌化合物的快速原型脱锌。在这些CrCl（3）介导的芳基锌化合物与醛的亲核加成反应中，芳基铬（III）可能是反应性中间体。
• A mechanistic study of the base-catalyzed methanolysis and hydrolysis of the hydrogen phthalate ester of 4-bromo-4′-nitrobenzhydrol
  作者：K. G. Rutherford、O. A. Mamer、B. K. Tang

  DOI：10.1139/v69-246

  日期：1969.5.1

  The hydrogen phthalate ester of 4-bromo-4′-nitrobenzhydrol has been subjected to base-catalyzed methanolysis and hydrolysis. In both cases the BAC2 mechanism has been observed. There is no evidence...

  4-溴-4'-硝基苯甲醇的邻苯二甲酸氢酯经过碱催化甲醇分解和水解。在这两种情况下都观察到了 BAC2 机制。没有证据...
• A simple rhodium-catalyzed addition reaction of aldehydes with arylboronic acids in aqueous γ-valerolactone
  作者：Min-xiao Xu、Kai-ming Zhang、Jie Zhang

  DOI：10.1016/j.mencom.2022.05.036

  日期：2022.5

  A simple rhodium-catalyzed addition reaction of aldehydes with arylboronic acids in aqueous γ-valerolactone provides the corresponding benzylic alcohols in moderate to good yields. Other organoboron reagents (boronic esters, aryl-trifluoroborates, etc.) also showed good compatibilities, albeit with relatively lower yields.

  醛与芳基硼酸在 γ-戊内酯水溶液中的简单铑催化加成反应以中等至良好的产率提供相应的苄醇。其他有机硼试剂（硼酸酯、芳基三氟硼酸盐等）也表现出良好的相容性，尽管产率相对较低。