4-chloro-2-methylthiophenol | 17178-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 4-chloro-2-methylthiophenol
• 英文别名: 4-chloro-2-methylbenzenethiol；4-Chlor-2-methyl-thiophenol
• CAS: 17178-01-7
• 化学式: C₇H₇ClS
• mdl: MFCD00041469
• 分子量: 158.652
• InChiKey: YIUPEFSJLWXHJR-UHFFFAOYSA-N

物化性质

• 沸点：
  117 °C(Press: 21 Torr)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4-chloro-2-methylthiophenol 在 磷酸酐 、 N-溴代丁二酰亚胺(NBS) 、 磷酸 、 sodium 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 25.0~180.0 ℃ 、2.0 kPa 条件下， 反应 4.5h， 生成 (E)-N-[(5-chloro-1-benzothiophen-7-yl)methyl]-N,6,6-trimethylhept-2-en-4-yn-1-amine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics

  摘要：

  Benzo[b]thiophene analouges of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.

  DOI：

  10.1021/jm00105a011
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 锌 作用下， 生成 4-chloro-2-methylthiophenol
  参考文献：
  名称：

  US1897516

  摘要：

  公开号：

文献信息

• Process for phenol alkylthiolation and its application to the synthesis
  申请人：Societe Nationale Elf Aquitaine (Production)

  公开号：US05113019A1

  公开（公告）日：1992-05-12

  The invention relates to the preparation of alkylthiophenols by reaction of a dialkyl disulphide with a phenol. In the process according to the invention, the reaction is carried out in the presence of aluminum chloride or of ferric chloride in a solvent of the alkylbenzene type or, soley in the case of methylthiolation, in an excess of dimethyl disulphide. This process makes it possible, in particular to obtain, with a selectivity and in a yield which are excellent, 2-alkylthiophenols which may then be converted into 4-acyl-2-alkylthiophenols by means of a reaction at a temperature ranging from 40.degree. to 100.degree. C. with a complex BF.sub.3 :2RCOOH where R denotes an alkyl or propenyl radical, in a proportion of 10 to 15 moles of complex per mole of 2-alkylthiophenol.

  该发明涉及通过二烷基二硫化物与酚的反应制备烷基硫代苯酚。根据该发明的工艺，反应在铝氯化物或三氯化铁存在下，在烷基苯类溶剂中进行，或者仅在甲硫基化的情况下，在过量的二甲基二硫化物中进行。该工艺特别能够以优异的选择性和产率获得2-烷基硫代苯酚，然后可以通过与复合物BF.sub.3:2RCOOH（其中R代表烷基或丙烯基基团）在40至100摄氏度的温度下反应，每摩尔2-烷基硫代苯酚使用10至15摩尔复合物，将其转化为4-酰基-2-烷基硫代苯酚。
• NOVEL CYCLOPENTANE DERIVATIVES
  申请人：Banner David

  公开号：US20100317647A1

  公开（公告）日：2010-12-16

  The invention relates to a compound of formula (I) wherein A 1 and R 1 to R 5 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  这项发明涉及一种化合物，其化学式为（I），其中A1和R1至R5的定义如描述和权利要求中所述。化合物的化学式（I）可用作药物。
• [EN] SYNTHETIC PENTASACCHARIDES HAVING SHORT HALF-LIFE AND HIGH ACTIVITY<br/>[FR] PENTASACCHARIDES SYNTHÉTIQUES AYANT UNE DEMI-VIE COURTE ET UNE ACTIVITÉ ÉLEVÉE
  申请人：ENDOTIS PHARMA

  公开号：WO2012172104A1

  公开（公告）日：2012-12-20

  The invention concerns a pentasaccharide compound of formula (I) and the salts thereof. The invention also concerns a pharmaceutical composition comprising the synthetic pentasaccharide compound of formula (I) and its salts. The invention further concerns these compounds for use as a medicament, and in particular intended to treat blood clotting disorders, to prevent ischaemia reperfusion injury associated with solid organ transplantation, or to reduce the risk of blood clotting in an extracorporeal blood circuit during cardiac surgery, extracorporeal membrane oxygenation, or during circulatory assistance such as artificial heart.

  这项发明涉及一种化学式(I)及其盐的五糖化合物。该发明还涉及一种包括合成五糖化合物及其盐的药物组合物。此外，该发明还涉及这些化合物作为药物的用途，特别是用于治疗血液凝块疾病，预防固体器官移植相关的缺血再灌注损伤，或在心脏手术、体外膜肺氧合或人工心脏等循环辅助过程中减少体外循环血路中的血液凝块风险。
• [EN] 3-(PHENYLSULFONYL)-[1,2,3]TRIAZOLO[1,5A]QUINAZOLIN-5(4H)-ONE DERIVATIVES<br/>[FR] DÉRIVÉS DE 3-(PHÉNYLSULFONYL)- [1,2,3]TRIAZOLO[1,5A]QUINAZOLIN-5(4H)-ONE
  申请人：BIOVERSYS AG

  公开号：WO2020109350A1

  公开（公告）日：2020-06-04

  The present invention relates to a compound according to formula (I), wherein R1 and R5 are independently selected from H, halogen, hydroxyl, NO2, CN, C1-C6-alkyl optionally substituted by one or more R11, C1-C6-alkoxy optionally substituted by one or more R11, C3-C6-cycloalkyl optionally substituted by one or more R11, -Cn-alkyl-N(R12)(R13) with n=0-3, -Cn-alkyl-C(O)N(R12)(R13) with n=0-3, -SO2-N(R14)-C(O)-R15; -Cn-alkyl-N(R14)-C(O)-R15 with n=0-3, -Cn-alkyl-C(O)-OR16 with n=0-3, -O(C1-C3-alkyl-O)m-C1-C3-alkyl-OR10 with m=0-3, -Cn-alkyl-OR16 with n=0-3, -NH-Cn-alkyl-R18 with n=0-3; -O-Cn-alkyl-R18 with n=0-3; -OPO(OR10)2, -PO(OR10)2, and a heterocycle optionally substituted by one or more R17; R3 is selected from halogen, hydroxyl, NO2, CN, C1-C6-alkyl optionally substituted by one or more R11, C1-C6-alkoxy optionally substituted by one or more R11, C3-C6-cycloalkyl optionally substituted by one or more R11, -Cn-alkyl-N(R12)(R13) with n=0-3, -Cn-alkyl-C(O)N(R12)(R13) with n=0-3, -SO2-N(R14)-C(O)-R15; -Cn-alkyl-N(R14)-C(O)-R15 with n=0-3, -Cn-alkyl-C(O)-OR16 with n=0-3, -O(C1-C3-alkyl-O)m-C1-C3-alkyl-OR10 with m=0-3, -Cn-alkyl-OR16 with n=0-3, -NH-Cn-alkyl-R18 with n=0-3; -O-Cn-alkyl-R18 with n=0-3; -OPO(OR10)2, -PO(OR10)2, and a heterocycle optionally substituted by one or more R17; R2 and R4 are independently selected from H, halogen, C1-C6-alkyl optionally substituted by one or more R11; R6, R7, R8 and R9 are independently selected from H, halogen, hydroxyl, NO2, CN, C1-C6-alkyl optionally substituted by one or more R11, C1-C6-alkoxy optionally substituted by one or more R11, C3-C6-cycloalkyl optionally substituted by one or more R11, -Cn-alkyl-N(R12)(R13) with n=0-3, -Cn-alkyl-C(O)N(R12)(R13) with n=0-3, -SO2-N(R12)(R13), -SO2-N(R14)-C(O)-R15; -Cn-alkyl-N(R14)-C(O)-R15 with n=0-3, -Cn-alkyl-C(O)-OR16 with n=0-3, -O(C1-C3-alkyl-O)m-C1-C3-alkyl-OR10 with m=0-3, -Cn-alkyl-OR16 with n=0-3, -NH-Cn-alkyl-R18 with n=0-3; -O-Cn-alkyl-R18 with n=0-3; -OPO(OR10)2, -PO(OR10)2, and a heterocycle optionally substituted by one or more R17; R10 is selected from H and C1-C6-alkyl optionally substituted by one or more R11; said one or more R11 is independently selected from Cl, F and hydroxy; R12, R13, R14, R15 and R16 are independently selected from H, C1-C6-alkyl optionally substituted by one or more R11, C3-C6-cycloalkyl optionally substituted by one or more R11, -SO2-C1-C6-alkyl optionally substituted by one or more R11, or wherein said R12 and R13 together with the nitrogen to which they are attached form a heterocycle optionally substituted by one or more R17; said one or more R17 is independently selected from halogen, hydroxy, NO2, CN, -N(R12)(R13), -C(O)-R16, -C(O)-OR16, -Cn-alkyl-OR16 with n=0-3, C1-C6-alkyl optionally substituted by one or more R11, and C1-C6-alkoxy optionally substituted by one or more R11; R18 is selected from -N(R12)(R13), -OR10, -C(O)-R16, -C(O)-OR16, -C(O)- N(R12)(R13), CN, and a heterocycle optionally substituted by one or more R17; and wherein at least one of R1, R2, R4, R5, R6, R7, R8 or R9 is not H; and pharmaceutically acceptable salts, stereoisomers, enantiomers, tautomers of the compounds of formula (I) as well as pharmaceutical compositions thereof and their uses in methods of reducing the virulence of bacteria that express AgrA, in methods for preventing or treating diseases caused or exacerbated by bacteria, preferably by Staphylococcus aureus, such as skin or lung infections or atopic dermatitis.

  本发明涉及一种化合物，其符合以下式（I），其中R1和R5分别选自H、卤素、羟基、NO2、CN、C1-C6烷基（可选地由一个或多个R11取代）、C1-C6烷氧基（可选地由一个或多个R11取代）、C3-C6环烷基（可选地由一个或多个R11取代）、-Cn-烷基-N（R12）（R13）（n=0-3）、-Cn-烷基-C（O）N（R12）（R13）（n=0-3）、-SO2-N（R14）-C（O）-R15；-Cn-烷基-N（R14）-C（O）-R15（n=0-3）、-Cn-烷基-C（O）-OR16（n=0-3）、-O（C1-C3-烷基-O）m-C1-C3-烷基-OR10（m=0-3）、-Cn-烷基-OR16（n=0-3）、-NH-Cn-烷基-R18（n=0-3）；-O-Cn-烷基-R18（n=0-3）；-OPO（OR10）2、-PO（OR10）2，以及可选地由一个或多个R17取代的杂环；R3选自卤素、羟基、NO2、CN、C1-C6烷基（可选地由一个或多个R11取代）、C1-C6烷氧基（可选地由一个或多个R11取代）、C3-C6环烷基（可选地由一个或多个R11取代）、-Cn-烷基-N（R12）（R13）（n=0-3）、-Cn-烷基-C（O）N（R12）（R13）（n=0-3）、-SO2-N（R14）-C（O）-R15；-Cn-烷基-N（R14）-C（O）-R15（n=0-3）、-Cn-烷基-C（O）-OR16（n=0-3）、-O（C1-C3-烷基-O）m-C1-C3-烷基-OR10（m=0-3）、-Cn-烷基-OR16（n=0-3）、-NH-Cn-烷基-R18（n=0-3）；-O-Cn-烷基-R18（n=0-3）；-OPO（OR10）2、-PO（OR10）2，以及可选地由一个或多个R17取代的杂环；R2和R4分别选自H、卤素、C1-C6烷基（可选地由一个或多个R11取代）；R6、R7、R8和R9分别选自H、卤素、羟基、NO2、CN、C1-C6烷基（可选地由一个或多个R11取代）、C1-C6烷氧基（可选地由一个或多个R11取代）、C3-C6环烷基（可选地由一个或多个R11取代）、-Cn-烷基-N（R12）（R13）（n=0-3）、-Cn-烷基-C（O）N（R12）（R13）（n=0-3）、-SO2-N（R12）（R13）、-SO2-N（R14）-C（O）-R15；-Cn-烷基-N（R14）-C（O）-R15（n=0-3）、-Cn-烷基-C（O）-OR16（n=0-3）、-O（C1-C3-烷基-O）m-C1-C3-烷基-OR10（m=0-3）、-Cn-烷基-OR16（n=0-3）、-NH-Cn-烷基-R18（n=0-3）；-O-Cn-烷基-R18（n=0-3）；-OPO（OR10）2、-PO（OR10）2，以及可选地由一个或多个R17取代的杂环；R10选自H和C1-C6烷基（可选地由一个或多个R11取代）；所述的一个或多个R11分别选自Cl、F和羟基；R12、R13、R14、R15和R16分别选自H、C1-C6烷基（可选地由一个或多个R11取代）、C3-C6环烷基（可选地由一个或多个R11取代）、-SO2-C1-C6烷基（可选地由一个或多个R11取代），或其中所述的R12和R13与它们连接的氮一起形成一个可选地由一个或多个R17取代的杂环；所述的一个或多个R17分别选自卤素、羟基、NO2、CN、-N（R12）（R13）、-C（O）-R16、-C（O）-OR16、-Cn-烷基-OR16（n=0-3）、C1-C6烷基（可选地由一个或多个R11取代）和C1-C6烷氧基（可选地由一个或多个R11取代）；R18选自-N（R12）（R13）、-OR10、-C（O）-R16、-C（O）-OR16、-C（O）-N（R12）（R13）、CN，以及可选地由一个或多个R17取代的杂环；其中R1、R2、R4、R5、R6、R7、R8或R9中至少有一个不是H；以及所述的化合物的药学上可接受的盐、立体异构体、对映异构体、互变异构体，以及其在减少表达AgrA的细菌的毒力的方法中的药物组合物及其用途，用于预防或治疗由细菌引起或加重的疾病，优选由金黄色葡萄球菌引起的疾病，如皮肤或肺部感染或特应性皮炎。
• ESR Studies of Dibenzenesulfenamidyl Radicals
  作者：Yozo Miura、Noboru Makita、Masayoshi Kinoshita

  DOI：10.1246/bcsj.50.482

  日期：1977.2

  Dibenzenesulfenamidyl radicals (2) were generated by the oxidation of dibenzenesulfenamides (1), and their ESR and visible spectra were measured. The ESR spectra were split into a 1 : 1 : 1 triplet by the interaction with the nitrogen nucleus (aN=11.26–11.49 G); in some spectra, each of the triplet was further split by the interaction with the ring protons (ao−H=ap−H=0.48–0.70, am−H=0.18–0.22 G). The

  二苯次磺酰胺 (1) 氧化生成二苯次磺酰胺自由基 (2)，并测量其 ESR 和可见光谱。通过与氮核的相互作用，ESR 光谱被分成 1 : 1 : 1 三重峰 (aN=11.26–11.49 G)；在一些光谱中，每个三重态都通过与环质子的相互作用进一步分裂（ao-H=ap-H=0.48-0.70，am-H=0.18-0.22 G）。g 值位于 2.0080–2.0083 的范围内。从结果可以得出结论，未成对电子主要分布在氮和两个硫原子上。2 衰变的动力学研究表明， 2 以二级动力学衰变并且对大气氧不敏感。

表征谱图