4′-(hydroxymethyl)biphenyl-2-carbaldehyde | 893738-89-1

• 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′-(hydroxymethyl)biphenyl-2-carbaldehyde
• 英文别名: 4'-(hydroxymethyl)biphenyl-2-carbaldehyde；4'-(Hydroxymethyl)[1,1'-biphenyl]-2-carbaldehyde；2-[4-(hydroxymethyl)phenyl]benzaldehyde
• CAS: 893738-89-1
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: BFHLBFRPIPLEOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4′-(hydroxymethyl)biphenyl-2-carbaldehyde 在 四溴化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以41%的产率得到4'-(bromomethyl)biphenyl-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and Affinity Evaluation for AT1 Receptor of Phenylsalicylaldoxime-Derivatives Structurally Related to Sartans

  摘要：

  In this work we reported the synthesis of new potential AT1 antagonists through the replacement of the biphenyltetrazole portion of the losartan with biphenylaldoximic (2) and phenylsalicylaldoximic (3a) moieties. Moreover, also the trifluoromethylpyrazole analogue of 3a (3b) was prepared. The new compounds synthesized were evaluated for their AT1 affinity through binding assay carried out on rat liver membranes using [(125)I]Sar1,Ile8-angiotensina II as radioligand.

  DOI：

  10.3987/com-07-11309
• 作为产物：
  描述：

  4-羟甲基苯硼酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 trans-bis(triphenylphosphine)palladium dichloride 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以60%的产率得到4′-(hydroxymethyl)biphenyl-2-carbaldehyde
  参考文献：
  名称：

  N-甲苯磺酰hydr与末端炔烃的铜催化交叉偶合反应合成菲

  摘要：

  探索了通过芳族甲苯磺酰hydr与末端炔烃的铜催化反应合成菲的新方法。该反应通过形成烯丙基中间体和随后的六-π电子环化-异构化而进行，从而以高收率获得了菲衍生物。转化可以通过两种方式进行：（1）用ñ -tosylhydrazones从[1,1'-联苯] -2- carbaldehydes和末端炔烃的原料和（2）与衍生ñ -tosylhydrazones从芳香醛和衍生以2-炔基联苯为原料。这种新的菲合成使用容易获得的原料和廉价的铜催化剂，并且具有广泛的官能团相容性。

  DOI：

  10.1021/jo501489c

文献信息

• Direct Excitation of Aldehyde to Activate the C( <i>sp</i> ^<i>2</i> )−H Bond by Cobaloxime Catalysis toward Fluorenones Synthesis with Hydrogen Evolution
  作者：Jia‐Dong Guo、Ya‐Jing Chen、Chen‐Hong Wang、Qiao He、Xiu‐Long Yang、Tian‐Yu Ding、Ke Zhang、Rui‐Nan Ci、Bin Chen、Chen‐Ho Tung、Li‐Zhu Wu

  DOI：10.1002/anie.202214944

  日期：2023.2.6

  highly reactive photoexcited triplet state of aromatic aldehyde intermediates is intercepted by the catalyst in the ground state, thus leading to the synthesis of a series of fluorenones, xanthones and thioxanthones in good to excellent yields without any external oxidants and with hydrogen as the byproduct.

  已经成功开发了通过钴肟催化直接激发醛以激活其 C ( sp 2 )-H 键。在照射下，芳香醛中间体的高反应性光激发三重态被基态催化剂拦截，从而导致在没有任何外部氧化剂和氢作为副产品。
• N-Tosylhydrazine-mediated deoxygenative hydrogenation of aldehydes and ketones catalyzed by Pd/C
  作者：Lei Zhou、Zhenxing Liu、Yizhou Liu、Yan Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2013.05.070

  日期：2013.7

  A mild and efficient method for the deoxygenative hydrogenation of aldehydes and ketones has been developed. The reaction is mediated by N-tosylhydrazine with H-2 (1 atm) as the reductant and 10% Pd/C as the catalyst. (C) 2013 Elsevier Ltd. All rights reserved.
• Expeditious Synthesis of Phenanthrenes via CuBr₂-Catalyzed Coupling of Terminal Alkynes and <i>N-</i>Tosylhydrazones Derived from <i>O</i>-Formyl Biphenyls
  作者：Fei Ye、Yi Shi、Lei Zhou、Qing Xiao、Yan Zhang、Jianbo Wang

  DOI：10.1021/ol201788v

  日期：2011.10.7

  A new method for the synthesis of phenanthrenes via ligand-free CuBr2-catalyzed coupling/cyclization of terminal alkynes with N-tosylhydrazones derived from o-formyl biphenyls has been developed. This new synthesis has wide range of functional group compatibility.
• Synthesis and Affinity Evaluation for AT1 Receptor of Phenylsalicylaldoxime-Derivatives Structurally Related to Sartans
  作者：Simona Rapposelli、Serena Cuboni、Maria Digiacomo、Antonio Lucacchini、Filippo Minutolo、Maria Letizia Trincavelli、Aldo Balsamo

  DOI：10.3987/com-07-11309

  日期：——

  In this work we reported the synthesis of new potential AT1 antagonists through the replacement of the biphenyltetrazole portion of the losartan with biphenylaldoximic (2) and phenylsalicylaldoximic (3a) moieties. Moreover, also the trifluoromethylpyrazole analogue of 3a (3b) was prepared. The new compounds synthesized were evaluated for their AT1 affinity through binding assay carried out on rat liver membranes using [(125)I]Sar1,Ile8-angiotensina II as radioligand.
• Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of <i>N</i>-Tosylhydrazones with Terminal Alkynes
  作者：Mohammad Lokman Hossain、Fei Ye、Zhenxing Liu、Ying Xia、Yi Shi、Lei Zhou、Yan Zhang、Jianbo Wang

  DOI：10.1021/jo501489c

  日期：2014.9.19

  for the synthesis of phenanthrenes through the copper-catalyzed reaction of aromatic tosylhydrazones with terminal alkynes is explored. The reaction proceeds via the formation of an allene intermediate and subsequent six-π-electron cyclization–isomerization, affording phenanthrene derivatives in good yields. The transformation can be performed in two ways: (1) with N-tosylhydrazones derived from [1,1

  探索了通过芳族甲苯磺酰hydr与末端炔烃的铜催化反应合成菲的新方法。该反应通过形成烯丙基中间体和随后的六-π电子环化-异构化而进行，从而以高收率获得了菲衍生物。转化可以通过两种方式进行：（1）用ñ -tosylhydrazones从[1,1'-联苯] -2- carbaldehydes和末端炔烃的原料和（2）与衍生ñ -tosylhydrazones从芳香醛和衍生以2-炔基联苯为原料。这种新的菲合成使用容易获得的原料和廉价的铜催化剂，并且具有广泛的官能团相容性。