2-mercaptodiphenylmethane | 120454-34-4

• 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-mercaptodiphenylmethane
• 英文别名: 2-benzylbenzenethiol
• CAS: 120454-34-4
• 化学式: C₁₃H₁₂S
• 分子量: 200.304
• InChiKey: QTKHXEAIGWJFPO-UHFFFAOYSA-N

物化性质

• 沸点：
  321.0±11.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 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：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-mercaptodiphenylmethane 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-((2-phenylmethylphenylsulfonyl)methyl)-2-ethylhexanal
  参考文献：
  名称：

  Discovery of Potent, Nonsystemic Apical Sodium-Codependent Bile Acid Transporter Inhibitors (Part 1)

  摘要：

  Elevated plasma levels of low-density lipoprotein (LDL) cholesterol are a major risk factor for atherosclerosis leading to coronary artery disease (CAD), which remains the main cause of mortality in Western society. We believe that by preventing the reabsorption of bile acids, a minimally absorbed apical sodium-codependent bile acid transporter (ASBT) inhibitor would lower the serum cholesterol without the potential systemic side effects of an absorbed drug. A series of novel benzothiepines (3R,3R'-2,3,4,5-tetrahydro-5-aryl-l-benzothiepin-4-ol 1,1-dioxides) were synthesized and tested for their ability to inhibit the apical sodium dependent bile acid transport (ASBT)-mediated uptake of [C-14]taurocholate (TC) in H14 cells. A 3R,4.R,5R13S,4S,5S racemate was found to have greater potency than the other three possible racemates. Addition of electron-donating groups such as a dimethylamino substituent at the 7 position greatly enhanced potency, and incorporation of a long-chain quaternary ammonium substituent on the 5-phenyl ring was useful in minimizing systemic exposure of this locally active ASBT inhibitor while also increasing water solubility and maintaining potency. The reported results describe the synthesis and SAR development of this benzothiepine class of ASBT inhibitors resulting in an 6000-fold improvement in ASBT inhibition with desired minimal systemic exposure of this locally acting drug candidate.

  DOI：

  10.1021/jm040215+
• 作为产物：
  描述：

  N-[(2-methylsulfanylphenyl)-phenylmethylidene]hydroxylamine 在 ammonium hydroxide 、 sodium 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 18.5h， 生成 2-mercaptodiphenylmethane
  参考文献：
  名称：

  缩合杂环。九。吡咯并[ 2,1- c ] [1,4]苯并噻氮平。3-（二甲基氨基）甲基衍生物的合成

  摘要：

  描述了3-（二甲基氨基）甲基-5 H，11 H-吡咯并[2,1- c ] [1,4]苯并硫氮杂derivatives衍生物2a-c的合成，该化合物可能具有显着的中枢神经系统（CNS）活性。基本侧链是通过曼尼希缩合与预先形成的杂环系统1a-c引入的。新颖5-苯基5的合成ħ，11 ħ吡咯并[2,1- c ^ ] [1,4]苯并硫氮杂1C通过亲核芳族氟化物置换的环化和试图替代路线1c中通过还报道了Pummerer重排环化。还提出了意外地形成吡咯-2-甲醛的机理。

  DOI：

  10.1016/s0040-4020(96)00342-0

文献信息

• Benzyl anion transfer in the fragmentation of N-(phenylsulfonyl)-benzeneacetamides: a gas-phase intramolecular S_NAr reaction
  作者：Shanshan Shen、Yunfeng Chai、Yaqin Liu、Chang Li、Yuanjiang Pan

  DOI：10.1039/c5ob01582k

  日期：——

  substitution (SNAr) during the course of tandem mass spectrometry of deprotonated N-(phenylsulfonyl)-benzeneacetamide. Upon collisional activation, the formation of the initial ion/neutral complex ([C6H5CH2−/C6H5SO2NCO]), which was generated by heterolytic cleavage of the CH2–CO bond, is proposed as the key step. Subsequently, the anionic counterpart, benzyl anion, is transferred to conduct the intra-complex

  在这项研究中，我们报告了在去质子化的N-（苯基磺酰基）-苯乙酰胺串联质谱过程中通过分子内芳香族亲核取代（S N Ar）气相气相苄基阴离子转移。一旦碰撞活化，初始离子的形成中性络合物（[C / 6 ħ 5 CH 2 - / C 6 H ^ 5 SO 2 NCO]），这是由CH的异裂产生的2 -CO键，被提议作为关键步骤。随后，将阴离子对应物苄基阴离子转移以进行内络合物S NAr反应。失去中性HNCO后，该中间体在m / z 231处产生产物离子B，通过比较多级光谱与去质子化的2-苄基苯亚磺酸和（苄基磺酰基）苯的谱图确认了其结构。此外，帧内复杂质子转移也是复杂的[C内观察到6 ħ 5 CH 2 - / C 6 H ^ 5 SO 2 NCO]以产生产物离子Ç在米/ Ž 182. INC介导的机制被证实理论计算，同位素实验，击穿曲线，取代基实验，等。这项工作可以进一步了解气态苄基阴离子的理化性质。
• Pyrrole derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：FISONS plc

  公开号：EP0300688A1

  公开（公告）日：1989-01-25

  Compounds of formula I, wherein R₁, R₂, R₃ and R₅ have the meanings defined in the specification, G2 represents a chain -(CH₂)z(W)y-, in which W has various meanings including C=O, and up to two of the methylene segments in the chain (CH₂)z are optionally replaced by -NH- and one segment is optionally replaced by -O- or -(C=NR₄₀)-, and the chain is optionally unsaturated and optionally substituted, and A is a 5- or 6-membered ring or a bicyclic or tricyclic fused ring system, A being optionally substituted by various substituents, possess useful pharmacological properties, in particular as cardiotonics. Also described are processes for the preparation of compounds of formula I, pharmaceutical compositions containing them and methods of treatment involving their use.

  式I的化合物，其中R₁、R₂、R₃和R₅的含义如规范中定义，G2代表一个链-(CH₂)z(W)y-，其中W具有包括C=O在内的各种含义，并且链中的(CH₂)z的最多两个亚甲基段可以选择性地被-NH-替换，一个段可以选择性地被-O-或-(C=NR₄₀)-替换，链可以是不饱和的和/或选择性地被取代的，A是一个5-或6-成员环或一个双环或三环融合环系统，A可以选择性地被各种取代基取代，具有有用的药理学性质，尤其是作为心力衰竭药。还描述了制备式I化合物的方法、含有它们的制药组合物以及涉及其使用的治疗方法。
• Benzylic C−H Functionalisation by [Et ₃ SiH+KO ^<i>t</i> Bu] leads to Radical Rearrangements in <i>o‐</i> tolyl Aryl Ethers, Amines and Sulfides
  作者：Jude N. Arokianathar、Krystian Kolodziejczak、Frances E. Bugden、Kenneth F. Clark、Tell Tuttle、John A. Murphy

  DOI：10.1002/adsc.202000356

  日期：2020.5.26

  rearrangement products. The rearrangements arise from formation of benzyl radicals, likely formed through hydrogen atom abstraction by triethylsilyl radicals. The rearrangements involve cyclisation of the benzyl radical onto the partner arene, which, from computation, is the rate determining step. In the case of diaryl ethers, Truce‐Smiles rearrangements arise from radical cyclisations to form 5‐membered

  Et 3 SiH + KO t Bu与具有邻烷基的二芳基醚，硫化物和胺的反应会导致重排产物。该重排是由苄基的形成引起的，该苄基的形成可能是通过三乙基甲硅烷基基团夺取氢原子而形成的。重排涉及将苄基环化到伙伴芳烃上，这从计算上是速率确定步骤。在二芳基醚的情况下，Truce-Smiles重排是由自由基环化形成的5元环，但对于二芳基胺，则观察到环化形成了二氢ac啶。
• Circumventing Anti-Androgen Resistance by Molecular Design
  作者：Paula L. McGinley、John T. Koh

  DOI：10.1021/ja0701154

  日期：2007.4.1

  Trp741→Cys that cause anti-androgens such as flutamide and bicalutamide to function as agonists are likely associated with anti-androgen withdrawal syndrome in PCa therapy. The recently solved crystal structure of bicalutamide was used to design analogues that would complement the Trp741→Leu mutation, effectively restoring antagonist action of the ligand. Three out of the six designed analogues showed potent

  核/类固醇激素受体 (NHR) 作为参与发育和体内平衡的不同基因组的配体依赖性转录调节因子发挥作用。NHR 成员雄激素受体 (AR) 的突变与激素疗法在前列腺癌 (PCa) 治疗中的失败有关。已经提出AR突变如Thr877→Ala、Trp741→Leu和Trp741→Cys导致抗雄激素如氟他胺和比卡鲁胺作为激动剂起作用，可能与PCa治疗中的抗雄激素戒断综合征有关。最近解决的比卡鲁胺晶体结构用于设计类似物，以补充 Trp741→Leu 突变，有效恢复配体的拮抗作用。
• Novel benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
  申请人：G.D. Searle & Co.

  公开号：US20020013476A1

  公开（公告）日：2002-01-31

  Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals.

  提供了新型苯并噻吩类化合物及其衍生物和类似物；含有它们的药物组合物；以及在医学中使用这些化合物和组合物的方法，特别是在哺乳动物中预防和治疗高脂血症状，如与动脉粥样硬化或高胆固醇血症相关的情况。