4-(3-iodopropoxy)biphenyl | 380364-00-1

• 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-(3-iodopropoxy)biphenyl
• 英文别名: 4-(3-iodopropoxy)-1,1'-biphenyl；1-(3-Iodopropoxy)-4-phenylbenzene
• CAS: 380364-00-1
• 化学式: C₁₅H₁₅IO
• 分子量: 338.188
• InChiKey: MELPLEJFVBFGTB-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C(Solv: ligroine (8032-32-4))
• 沸点：
  410.3±38.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(3-iodopropoxy)biphenyl 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 39.0h， 生成 3-({methyl[3-(4-phenylphenoxy)propyl]amino}methyl)phenyl N-methylcarbamate
  参考文献：
  名称：

  Acetylcholinesterase Inhibitors:  SAR and Kinetic Studies on ω-[N-Methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyaryl Derivatives

  摘要：

  In this work, we further investigated a class of carbamic cholinesterase inhibitors introduced in a previous paper (Rampa et al. J. Med. Chem. 1998, 41, 3976). Some new omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyaryl analogues were designed, synthesized, and evaluated for their inhibitory activity against both acetyleholinesterase (AChE) and butyrylcholinesterase (BuChE). The structure of the lead compound (xanthostigmine) was systematically varied with the aim to optimize the different parts of the molecule. Moreover, such a structure-activity relationships (SAR) study was integrated with a kinetic analysis of the mechanism of AChE inhibition for two representative compounds. The structural modifications lead to a compound (12b) showing an IC50 value for the AChE inhibition of 0.32 +/- 0.09 nM and to a group of BuChE inhibitors also active at the nanomolar level, the most potent of which (15d) was characterized by an IC50 value of 3.3 +/- 0.4 nM. The kinetic analysis allowed for clarification of the role played by different molecular moieties with regard to the rate of AChE carbamoylation and the duration of inhibition. On the basis of the results presented here, it was concluded that the cholinesterase inhibitors of this class possess promising characteristics in view of a potential development as drugs for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm010914b
• 作为产物：
  描述：

  4-(3-chloropropoxy)-1,1'-biphenyl 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 4.0h， 以70%的产率得到4-(3-iodopropoxy)biphenyl
  参考文献：
  名称：

  Acetylcholinesterase Inhibitors:  SAR and Kinetic Studies on ω-[N-Methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyaryl Derivatives

  摘要：

  In this work, we further investigated a class of carbamic cholinesterase inhibitors introduced in a previous paper (Rampa et al. J. Med. Chem. 1998, 41, 3976). Some new omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyaryl analogues were designed, synthesized, and evaluated for their inhibitory activity against both acetyleholinesterase (AChE) and butyrylcholinesterase (BuChE). The structure of the lead compound (xanthostigmine) was systematically varied with the aim to optimize the different parts of the molecule. Moreover, such a structure-activity relationships (SAR) study was integrated with a kinetic analysis of the mechanism of AChE inhibition for two representative compounds. The structural modifications lead to a compound (12b) showing an IC50 value for the AChE inhibition of 0.32 +/- 0.09 nM and to a group of BuChE inhibitors also active at the nanomolar level, the most potent of which (15d) was characterized by an IC50 value of 3.3 +/- 0.4 nM. The kinetic analysis allowed for clarification of the role played by different molecular moieties with regard to the rate of AChE carbamoylation and the duration of inhibition. On the basis of the results presented here, it was concluded that the cholinesterase inhibitors of this class possess promising characteristics in view of a potential development as drugs for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm010914b

文献信息

• Transition Metal Free Stannylation of Alkyl Halides: The Rapid Synthesis of Alkyltrimethylstannanes
  作者：Songyi Li、Chang Lian、Guanglu Yue、Jianning Zhang、Di Qiu、Fanyang Mo

  DOI：10.1021/acs.joc.1c03135

  日期：2022.3.18

  A transition metal free stannylation reaction of alkyl bromides and iodides with hexamethyldistannane has been developed. This protocol is operationally convenient and features a rapid reaction and good functional group tolerance. A wide range of functionalized primary and secondary alkyl and benzyl trimethyl stannanes are prepared in moderate to excellent yields. The success of the gram-scale procedure

  已经开发了烷基溴化物和碘化物与六甲基二锡烷的无过渡金属的锡烷基化反应。该协议操作方便，反应速度快，官能团耐受性好。以中等至优异的产率制备了范围广泛的官能化伯和仲烷基和苄基三甲基锡烷。克级程序和串联 Stille 偶联反应的成功使该协议展示了在有机合成中的应用潜力。实验和理论研究都揭示了这种酸化反应的机理细节。
• 系列烷基三甲基锡化合物及其制备方法与应用
  申请人：天津师范大学

  公开号：CN112979693B

  公开（公告）日：2023-03-28

  本发明公开了系列烷基三甲基锡化合物及其制备方法与应用。它是将烷基碘化物、碱、六甲基二锡置于溶剂中均匀混合均匀，在30℃下反应24小时，反应结束后进行浓缩；再进行柱层析以得到纯净的烷基三甲基锡产物。本发明采用的原料为烷基碘化物，较已有的采用烷基卤化物与格氏试剂为原料的反应方法，是一个重大的补充，并且原料来源广泛，便宜易得，生产成本低，室温下反应，未使用过渡金属催化剂。本发明方法所涉及的反应对官能团具有很好的容忍性和普适性，烷基上的取代基可以为氢、甲基、叔丁基、氟、氯、溴、氰基、三氟甲基、甲氧基、甲基磺酰基或乙酯基等。