2-((bis(4-methoxyphenyl)methyl)thio)ethan-1-ol | 908583-30-2

• 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: 2-((bis(4-methoxyphenyl)methyl)thio)ethan-1-ol
• CAS: 908583-30-2
• 化学式: C₁₇H₂₀O₃S
• 分子量: 304.41
• InChiKey: JOVBYCOVCJLWOA-UHFFFAOYSA-N

物化性质

• 沸点：
  466.3±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((bis(4-methoxyphenyl)methyl)thio)ethan-1-ol 在 咪唑 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of (R)-N-(diarylmethylthio/sulfinyl)ethyl/propyl-piperidine-3-carboxylic acid hydrochlorides as novel GABA uptake inhibitors

  摘要：

  A series of new (R)-1-(2-diarylmethylthio/sulfinyl) ethyl-pipei-idine-3-carboxylic acid hydrochlorides 5a-d/6a-d and (R)-1(3-diarylmethylthio) propyl-piperidine-3-carboxylic acid hydrochlorides 5'a-d were synthesized and evaluated as gamma-aminobutyric acid uptake inhibitors through cultured cell lines expressing mouse GAT1. Biological screening results demonstrated that the compounds 6a-d with diarylmethylsulfinyl ethyl side chain show more potent GAT-1 inhibitory activities than 5a-d/5'a-d with diary]methylthio ethyl/propyl moieties. Some of them, such as 6a, exhibited excellent inhibitions of [3 H]-GABA uptake in cultured cells, which is 496-fold higher than (R)-nipecotic acid and 11.5 times less than tiagabine. The synthesis and structure-activity relationships are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.010
• 作为产物：
  描述：

  二甲氧基苯甲醇 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 2-((bis(4-methoxyphenyl)methyl)thio)ethan-1-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of (R)-N-(diarylmethylthio/sulfinyl)ethyl/propyl-piperidine-3-carboxylic acid hydrochlorides as novel GABA uptake inhibitors

  摘要：

  A series of new (R)-1-(2-diarylmethylthio/sulfinyl) ethyl-pipei-idine-3-carboxylic acid hydrochlorides 5a-d/6a-d and (R)-1(3-diarylmethylthio) propyl-piperidine-3-carboxylic acid hydrochlorides 5'a-d were synthesized and evaluated as gamma-aminobutyric acid uptake inhibitors through cultured cell lines expressing mouse GAT1. Biological screening results demonstrated that the compounds 6a-d with diarylmethylsulfinyl ethyl side chain show more potent GAT-1 inhibitory activities than 5a-d/5'a-d with diary]methylthio ethyl/propyl moieties. Some of them, such as 6a, exhibited excellent inhibitions of [3 H]-GABA uptake in cultured cells, which is 496-fold higher than (R)-nipecotic acid and 11.5 times less than tiagabine. The synthesis and structure-activity relationships are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.010

文献信息

• Sequential Selective C−H and C(sp ³ )− ⁺ P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds
  作者：K. Naresh Babu、Fedaa Massarwe、Israa Shioukhi、Ahmad Masarwa

  DOI：10.1002/anie.202111164

  日期：2021.12.6

  of the resulting phosphonium salt building blocks was demonstrated by the chemoselective post-functionalization of benzylic C(sp3 )-+ PPh3 groups to achieve aminations, thiolations, and arylations. In this way, benzhydrylamines, benzhydrylthioethers, and triarylmethanes, structural motifs that are present in many pharmaceuticals and agrochemicals, are readily accessed. These include the synthesis of

  含有 C(sp3 )-+ P 键的有机鏻盐是有机合成中用于构建 CC 双键的最常用试剂之一。然而，它们用作 C 选择性亲电基团的情况很少见。在这里，我们探索了一种有效且通用的无过渡金属方法，用于顺序化学和区域选择性 CH 和 C(sp3 )-+ P 键功能化。在本研究中，CH 烷基化导致二苯甲基三芳基鏻盐的合成是通过简单和市售起始材料的一锅四组分交叉偶联反应实现的。通过对苄基 C(sp3 )-+ PPh3 基团进行化学选择性后官能化以实现胺化、硫醇化和芳基化，证明了所得鏻盐结构单元的实用性。这样，二苯甲基胺、二苯甲基硫醚、和三芳基甲烷是许多药物和农用化学品中存在的结构基序，很容易获得。其中包括仅用两到三个步骤从简单材料合成两种抗癌剂。此外，还开发了使用二苯甲基鏻盐对生物活性药物进行后期功能化的协议。这种新方法应该为学术和药物研究中的应用提供新的转变。