benzhydrylisothiouronium chloride | 60282-85-1

• 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: benzhydrylisothiouronium chloride
• 英文别名: Benzhydryl-isothioharnstoff；2-benzhydryl-isothiourea; hydrochloride；S-benzhydryl-isothiourea; hydrochloride；S-Benzhydryl-isothioharnstoff; Hydrochlorid；S-Diphenylmethyl-isothiuronium-chlorid, S-Benzhydryl-isothiuronium-chlorid；benzhydrylthiocarboxamidine hydrochloride；diphenylmethylthiouronium chloride；Benzhydryl thiuronium chloride；[amino(benzhydrylsulfanyl)methylidene]azanium;chloride
• CAS: 60282-85-1
• 化学式: C₁₄H₁₄N₂S*ClH
• 分子量: 278.805
• InChiKey: IQFNCNHJOCSBHF-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzhydrylisothiouronium chloride 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 二苯基硫代甲烷
  参考文献：
  名称：

  Structure−Activity Relationships in the Binding of Chemically Derivatized CD4 to gp120 from Human Immunodeficiency Virus

  摘要：

  The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp 120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp 120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp 120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.

  DOI：

  10.1021/jm070564e
• 作为产物：
  描述：

  硫脲 、 二苯氯甲烷 在 乙醇 作用下， 生成 benzhydrylisothiouronium chloride
  参考文献：
  名称：

  一些苯甲酰基砜的制备和性质。

  摘要：

  DOI：

  10.1021/ja01191a090

文献信息

• [EN] IMPROVED PROCESS FOR PREPARING BENZHYDRYLTHIOACETAMIDE<br/>[FR] PROCEDE AMELIORE PERMETTANT DE PREPARER UN BENZHYDRYLTHIOACETAMIDE
  申请人：MALLINCKRODT INC

  公开号：WO2005042479A1

  公开（公告）日：2005-05-12

  The present invention is directed to an improved process for preparing modafinil wherein benzhydrylthioacetate is prepared in high yield and purity by the reaction of a haloacetate with the reaction product of thiourea and benzhydrol. The reaction employing the haloacetate is conducted in a solvent comprising an organic solvent such as methanol having dissolved therein an organic base or an inorganic basic salt such as sodium bicarbonate. The resulting benzhydrylthioacetate can be amidated and then oxidized to provide the pharmaceutical grade modafinil in high yield and purity.

  本发明涉及一种改进的制备莫达非尼的方法，其中通过卤代醋酸酯与硫脲和苄基醇的反应产生高收率和纯度的苄基硫代乙酸酯。使用卤代醋酸酯进行的反应在包含有机溶剂（如甲醇）和有机碱或无机碱性盐（如碳酸氢钠）的溶剂中进行。最终产生的苄基硫代乙酸酯可以被酰胺化，然后氧化以提供高收率和纯度的药用级莫达非尼。
• Sulfoxide-Chelated Ruthenium Benzylidene Catalyst: a Synthetic Study on the Utility of Olefin Metathesis
  作者：Karolina Żukowska、Łukasz Pączek、Karol Grela

  DOI：10.1002/cctc.201600538

  日期：2016.9.7

  We provide an experimental summary of selected advances in olefin metathesis methodology that were reported over the past decades. A stable and universal sulfoxide‐chelated ruthenium olefin metathesis catalyst [RuCl2(SIMes)(=CH−C6H4−S(O)Ph)], SIMes=1,3‐bis(2,4,6‐trimethylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene, was introduced and its application profile was studied in detail. A range of model substrates

  我们提供了在过去几十年中报道的烯烃复分解方法的部分进展的实验总结。稳定且通用的亚砜螯合钌烯烃复分解催化剂[RuCl 2（SIMes）（= CH-C 6 H 4-S（O）Ph）]，介绍了SIMes = 1,3-双（2,4,6-三甲基苯基）-4,5-二氢咪唑-2-亚基，并详细研究了其应用概况。已开发出一系列天然来源的模型底物，并成功地通过反应的变体进行了复分解，例如烯-炔，交叉或闭环复分解。报告的所有反应均在未经预处理的溶剂和空气中进行，以证明系统的用户友好性。除了已报道的配合物表现出的强大的官能团耐受性外，还确定了其与多种溶剂的相容性以及其空气和湿气的稳定性。另外，如果在约溶剂沸点的温度下进行反应，则观察到提高反应效率的有趣效果。
• [EN] PROCESS FOR PREPARING POLYMORPHIC FORM (I) OF MODAFINIL<br/>[FR] PROCEDE DE PREPARATION D'UNE FORME POLYMORPHE DE MODAFINIL
  申请人：ERREGIERRE SPA

  公开号：WO2005000799A1

  公开（公告）日：2005-01-06

  A process is described for preparing polymorphic form (I) of modafinil with high yields and with low impurity content. The process comprises the steps of (a) reacting (diphenylmethyl)thioacetic acid with a C1-C5 alcohol,(b) oxidation of the resulting ester with hydreogen peroxide to give an ester of (diphenylmethyl)sulphinylacetic acid, (c) reaction with ammonia to form modafinil and (d) treatement with water and ethyl acetate. This process may comprise a further crystallisation in the presence of a mixture of DMF and acetone to further lower the impurities, and finally a possible crystallisation from DMF and water to increase its particle size.

  描述了一种制备莫达非尼的多形态形式(I)的方法，该方法具有高产率和低杂质含量。该过程包括以下步骤：(a) 用C1-C5醇反应(diphenylmethyl)thioacetic酸，(b) 氧化所得酯与过氧化氢反应以得到(diphenylmethyl)sulphinylacetic酸的酯，(c) 与氨反应形成莫达非尼，(d) 用水和乙酸乙酯处理。该过程可能包括在DMF和丙酮混合物存在下进一步结晶以进一步降低杂质，并最后可能在DMF和水中结晶以增加其粒径。
• Goerdeler,J.; El Tom,I., Chemische Berichte, 1965, vol. 98, p. 1544 - 1555
  作者：Goerdeler,J.、El Tom,I.

  DOI：——

  日期：——
• Timmerman; Rekker; Harms, Arzneimittel-Forschung/Drug Research, 1970, vol. 20, # 9, p. 1258 - 1259
  作者：Timmerman、Rekker、Harms、Nauta

  DOI：——

  日期：——