4-[(4-Methoxy-phenyl)-thiophen-2-yl-methyl]-phenol | 852287-08-2

• 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-[(4-Methoxy-phenyl)-thiophen-2-yl-methyl]-phenol
• 英文别名: 4-[(4-Methoxyphenyl)-thiophen-2-ylmethyl]phenol
• CAS: 852287-08-2
• 化学式: C₁₈H₁₆O₂S
• 分子量: 296.39
• InChiKey: HHTSSSRAILAYRY-UHFFFAOYSA-N

物化性质

• 沸点：
  451.4±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(4-Methoxy-phenyl)-thiophen-2-yl-methyl]-phenol 、 2-二乙氨基氯乙烷盐酸盐 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以72%的产率得到N,N-diethyl-2-[4-[(4-methoxyphenyl)-thiophen-2-ylmethyl]phenoxy]ethanamine
  参考文献：
  名称：

  含有三芳基甲烷的噻吩作为抗结核药。

  摘要：

  由二芳基甲醇的弗瑞德-克来福特烷基化反应，然后结合氨基烷基链，合成了一系列新的含噻吩的三芳基甲烷衍生物。对它们进行了针对结核分枝杆菌H37R（v）的评估，并在体外显示其活性在3.12-12.5 microg / mL的范围内。

  DOI：

  10.1016/j.bmcl.2007.10.083
• 作为产物：
  描述：

  4-甲氧基苯基溴化镁 在 硫酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.0h， 生成 4-[(4-Methoxy-phenyl)-thiophen-2-yl-methyl]-phenol
  参考文献：
  名称：

  An easy access to unsymmetric trisubstituted methane derivatives (TRSMs)

  摘要：

  A new series of unsymmetric trisubstituted methane derivatives (TRSMs) has been synthesized through Friedel Crafts alkylation of aromatic nucleophiles using acid-sensitive heleroaryl carbinols. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.001

文献信息

• Transition‐Metal‐Free Synthesis of Polyfunctional Triarylmethanes and 1,1‐Diarylalkanes by Sequential Cross‐Coupling of Benzal Diacetates with Organozinc Reagents
  作者：Baosheng Wei、Qianyi Ren、Thomas Bein、Paul Knochel

  DOI：10.1002/anie.202101682

  日期：2021.4.26

  A variety of functionalized triarylmethane and 1,1‐diarylalkane derivatives were prepared via a transition‐metal‐free, one‐pot and two‐step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross‐coupling is enabled by changing the solvent from THF to toluene, and a two‐step SN1‐type mechanism was proposed and evidenced by experimental studies. The

  通过无过渡金属的一锅两步程序制备了各种官能化三芳基甲烷和1,1-二芳基烷烃衍生物，其中包括各种二乙酸苯亚缩酯与有机锌试剂的反应。通过将溶剂从 THF 更改为甲苯，可以实现顺序交叉偶联，并提出了两步 S N 1 型机理，并通过实验研究证明了这一点。该方法的合成效用通过几种生物学相关分子的合成得到进一步证明，例如抗结核剂、抗乳腺癌剂、鞘氨醇-1-磷酸（S1P）受体调节剂的前体和FLAP抑制剂。
• Thiophene containing trisubstituted methanes [TRSMs] as identified lead against Mycobacterium tuberculosis
  作者：Priyanka Singh、Sudipta Kumar Manna、Amit Kumar Jana、Tiash Saha、Pankaj Mishra、Saurav Bera、Maloy Kumar Parai、Srinivas Lavanya Kumar M、Sankalan Mondal、Priyanka Trivedi、Vinita Chaturvedi、Shyam Singh、Sudhir Sinha、Gautam Panda

  DOI：10.1016/j.ejmech.2015.03.036

  日期：2015.5

  Triarylmethanes (TRAMs) and thiophene containing trisubstituted methanes (TRSMs) have been reported by us, having potential against Mycobacterium tuberculosis and Mycobacterium fortuitum strains, respectively. Further, extension through synthesis and biological evaluation of novel TRSMs resulted into an identified lead 36 (S006-830) [(diisopropyl-(2-4-[(4-methoxy-phenyl)- thiophen-2-yl-methyll-phenoxy}-ethyl)-amine)] with MIC: 1.33 mg/L, non-toxic against Vero C-1008 cell line with selectivity index >10, ex vivo efficacy equivalent to first line TB drugs-isoniazid (INH), rifampicin (RFM) and pyrazinamide (PZA) in the mouse and human macrophages, and lung CFU count of 2.2 x 10(7) (approximately 15 fold lesser than untreated mice, 31 x 10(7)) with efficacies comparable to ethambutol (EMB) (1.27 x 10(7)) and PZA (1.9 x 10(7)). Further, S006-830 also showed potent bactericidal activity against multi-drug resistant and single-drug resistant clinical isolates of M. tuberculosis. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Panda, Gautam; Parai, Maloy Kumar; Srivastava, Ajay Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 8, p. 1121 - 1127
  作者：Panda, Gautam、Parai, Maloy Kumar、Srivastava, Ajay Kumar、Chaturvedi, Vinita、Manju、Sinha, Sudhir

  DOI：——

  日期：——
• Thiophene containing triarylmethanes as antitubercular agents
  作者：Maloy Kumar Parai、Gautam Panda、Vinita Chaturvedi、Y.K. Manju、Sudhir Sinha

  DOI：10.1016/j.bmcl.2007.10.083

  日期：2008.1

  A new series of thiophene containing triarylmethane derivatives were synthesized from the Friedel-Crafts alkylation of diarylcarbinols followed by incorporation of amino alkyl chains. These were evaluated against Mycobacterium tuberculosis H37R(v) and showed the activity in the range of 3.12-12.5 microg/mL in vitro.

  由二芳基甲醇的弗瑞德-克来福特烷基化反应，然后结合氨基烷基链，合成了一系列新的含噻吩的三芳基甲烷衍生物。对它们进行了针对结核分枝杆菌H37R（v）的评估，并在体外显示其活性在3.12-12.5 microg / mL的范围内。
• An easy access to unsymmetric trisubstituted methane derivatives (TRSMs)
  作者：Sajal Kumar Das、Shagufta、Gautam Panda

  DOI：10.1016/j.tetlet.2005.03.001

  日期：2005.4

  A new series of unsymmetric trisubstituted methane derivatives (TRSMs) has been synthesized through Friedel Crafts alkylation of aromatic nucleophiles using acid-sensitive heleroaryl carbinols. (c) 2005 Elsevier Ltd. All rights reserved.