2-Butylmercapto-benzoylchlorid | 855272-65-0

• 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-Butylmercapto-benzoylchlorid
• 英文别名: 2-butylsulfanyl-benzoyl chloride；2-Butylmercapto-benzoesaeure-chlorid；2-(n-Butylthio)benzoyl chloride；2-butylsulfanylbenzoyl chloride
• CAS: 855272-65-0
• 化学式: C₁₁H₁₃ClOS
• 分子量: 228.743
• InChiKey: DZESFNIADKKHCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-羟乙基哌啶 、 2-Butylmercapto-benzoylchlorid 在 吡啶 、 乙醚 作用下， 生成 2-哌啶乙基 2-(丁基硫代)苯甲酸酯
  参考文献：
  名称：

  The Synthesis of Some Alkamine Esters of Alkylthiobenzoic Acids

  摘要：

  DOI：

  10.1021/ja01858a063
• 作为产物：
  描述：

  硫代水杨酸 在 sodium hydroxide 、 三氯氧磷 作用下， 生成 2-Butylmercapto-benzoylchlorid
  参考文献：
  名称：

  （2-烷基硫代苯甲酰基）二茂铁的合成，光谱表征和电化学性能。2-甲硫基，2-乙硫基和2-异丙硫基衍生物的晶体结构

  摘要：

  一锅法合成了七种新的（2-烷基硫代苯甲酰基）二茂铁，这是通过将二茂铁与相应的羧酸和三氯化磷原位生成的酰氯进行Friedel-Crafts酰化反应而实现的。所得化合物通过光谱数据（UV，IR，1 H和13NMR），而其电化学性质已通过循环伏安法研究。还报告了其中三个的单晶X射线结构测定。这三种衍生物均表现出分子内C–H…O相互作用，其中涉及环戊二烯基（Cp）环的供体和羰基氧作为受体。这种相互作用有利于两个部分的共面排列。符合C–O键的向量与相应的Cp平面之间的夹角均小于6.4°。常规的氢键在这三个晶体结构中都不存在，但是已经发现并详细分析了某些类型的C–H…O，C–H…S和C–H…π类型的弱分子间相互作用。

  DOI：

  10.1016/j.poly.2010.04.034

文献信息

• New series of thio-derivatives of basic benzhydryl ethers and thioethers
  申请人：HERMAN HUBNER OLUF

  公开号：US02830088A1

  公开（公告）日：1958-04-08

  The invention comprises thio- or sulphonyl-substituted basic benzhydryl ethers and thioethers having sedative properties and represented by the formula wherein R is hydrogen, chlorine, bromine or iodine; R1 and R2 are alkylsulphonyl, alkylmercapto, phenyl- or substituted phenylmercapto, cycloalkyl- or substituted cycloalkylmercapto or hydrogen, and may be the same except when one of them is hydrogen; Z is oxygen or sulphur; and X is dialkylaminoalkyl, morpholinyl-substituted alkyl, piperidyl-substituted alkyl or N-alkyl-substituted C-piperidyl; and their acid or quaternary ammonium salts. They may be prepared by reacting a benzhydryl halide of the formula with the appropriate amino-alcohol or amino-thio-alcohol or their alkali metal salts; or by reacting the amino-halide with an appropriately substituted benzhydrol or benzhydryl-thio-alcohol or an alkali metal salt thereof. Solvents may be present. Examples disclose the preparation of hydrochlorides or citrates of the following compounds: benzhydryl 2-dimethylaminoethyl sulphides in which the benzhydryl group is substituted by p-methyl, p-ethyl, p-isopropyl-, o-, m- and p-butyl-, m- and p-hexyl-, p-cyclohexyl-, p-octyl- and p-phenyl-mercapto groups and by p,p1-bis(n-hexyl-, propyl- and butyl-mercapto) groups and by p-butyl sulphonyl: the p-butyl- and m-bromo-p1-butylmercapto and p,p1-bis(butylmercapto)-benzyhydryl 2-diethyl aminoethyl sulphides: m- and p-butyl-mercapto-benzhydryl 2-dimethylaminoethyl ethers: p-butylmercaptobenzhydryl-4-dimethyl-aminobutyl ether: p-butylmercaptobenzhydryl 2-(4-morpholinyl) ethyl ether and sulphide; p-butyl mercaptobenzhydryl 2-dimethylaminopropyl ether and sulphide: p-butylmercaptobenzhydryl 4-(1-methyl)-piperidyl sulphide: p-methylmercaptobenzhydryl 2-(1 - piperidyl) - ethyl ether: p-hexylmercaptobenzhydryl 2-(4-morpholinyl)-ethyl sulphide. The p-alkylmercaptobenzhydryl chlorides, used as starting materials, are prepared by reducing the p-alkyl mercaptobenzophenones (obtained from the p-alkylphenyl sulphides) with zinc and sodium hydroxide to the alcohol and then saturating with anhydrous HCl. The p-phenylmercapto-derivative is similarly prepared. The m-alkyl mercaptobenzhydryl chlorides are similarly prepared from the m-alkylmercaptobenzophenones which are obtained from the m-alkylmercaptobenzoyl chloride, benzene and anhydrous AlCl3 in CS2. The alkylmercaptobenzhydryl mercaptans are prepared by boiling the chloride with thiourea yielding the alkylmercaptobenzhydrylisothiouronium chloride which is then hydrolysed with aqueous sodium hydroxide. p-Butyl sulphonylbenzophenone is obtained by oxidizing p-butyl mercaptobenzophenone with hydrogen peroxide in glacial acetic acid. m - Bromo - p1 - butylmercaptobenzhydryl chloride is prepared by reacting butyl phenyl sulphide with m-bromobenzoyl chloride by the Friedel-Crafts synthesis to yield m-bromo-p1-butylmercaptobenzophenone, which is reduced by zinc and KOH to the alcohol which is then treated with HCl. p - Bromophenyl - n - butyl sulphide, prepared by brominating p-n-butyl phenyl sulphide, is converted to p-butyl mercaptobenzoic acid by carbonation of a Grignard derivative with CO2. The acid chloride, obtained by treatment with thionyl chloride, is reacted with butyl phenyl sulphide as above, yielding p,p1-bis (butylmercapto)-benzophenone. This is reduced to give p,p1-bis(butylmercapto)-benzhydrol, which is treated with HCl to give the chloride. Similar methods produce the p,p1-bis(propyl-and hexyl-mercapto)-derivatives.

  这项发明包括具有镇静性能的硫代或磺代基本苯基二苯基醚和硫醚，其化学式表示为，其中R为氢、氯、溴或碘；R1和R2为烷基磺酰基、烷基硫醇基、苯基或取代苯基硫醇基、环烷基或取代环烷基硫醇基或氢，除非其中一个是氢；Z为氧或硫；X为二烷胺基烷基、吗啉基取代烷基、哌啶基取代烷基或N-烷基取代C-哌啶基；以及它们的酸或季铵盐。它们可以通过将化学式的二苯基卤化物与适当的氨基醇或氨基硫醇或它们的碱金属盐反应来制备；或者通过将氨基卤化物与适当取代的苯基醇或苯基硫醇醇或其碱金属盐反应来制备。溶剂可以存在。示例揭示了以下化合物的盐酸盐或柠檬酸盐的制备：苯基二甲基氨基乙基硫化物，其中苯基基被p-甲基、p-乙基、p-异丙基、o-、m-和p-丁基、m-和p-己基、p-环己基、p-辛基和p-苯基硫醇基取代，以及p,p1-双(n-己基、丙基和丁基硫醇基)基和p-丁基磺酰基取代；p-丁基和m-溴-p1-丁基硫醇基和p,p1-双(丁基硫醇基)-苯基二乙基氨基乙基硫化物；m-和p-丁基硫醇基苯基二甲基氨基乙基醚；p-丁基硫醇基苯基二(4-吗啉基)乙基醚和硫化物；p-丁基硫醇基苯基二甲基氨基丙基醚和硫化物；p-丁基硫醇基苯基四(1-甲基)-哌啶基硫化物；p-甲基硫醇基苯基二(1-哌啶基)-乙基醚；p-己基硫醇基苯基二(4-吗啉基)-乙基硫化物。作为起始原料使用的p-烷基硫醇基苯基氯化物是通过将p-烷基硫醇基苯酮（从p-烷基苯基硫醇基获得）与锌和氢氧化钠还原为醇，然后用无水HCl饱和得到的。p-苯基硫醇基衍生物类似制备。m-烷基硫醇基苯基氯化物类似地从m-烷基硫醇基苯酮制备，后者是通过m-烷基硫醇基苯酰氯、苯和无水AlCl3在CS2中反应获得的。烷基硫醇基苯基硫醇基硫醇通过将氯化物与硫脲沸腾制备，得到的烷基硫醇基苯基硫醇基硫脲盐随后与水合氢氧化钠水解。p-丁基磺酰基苯酮是通过在冰乙酸中用过氧化氢氧化p-丁基硫醇基苯酮得到的。m-溴-p1-丁基硫醇基苯基氯化物是通过将丁基苯硫化物与m-溴苯甲酰氯在Friedel-Crafts合成中反应得到m-溴-p1-丁基硫醇基苯酮，然后通过锌和KOH还原为醇，再用HCl处理得到。由溴化p-正丁基苯硫化物制备的p-溴苯基-n-正丁硫醚通过用CO2与格氏试剂衍生物碳化得到p-丁基硫醇基苯甲酸。酸氯化物通过与氯化硫酰反应得到，然后与p-正丁基苯硫化物反应，得到p,p1-双(正丁硫醇基)-苯酮。这经还原得到p,p1-双(正丁硫醇基)-苯醇，再经HCl处理得到氯化物。类似方法可制备p,p1-双(丙基和己基硫醇基)-衍生物。
• Local Anesthetics. I. β-Monoalkylaminoethyl Esters of Alkoxybenzoic Acids¹
  作者：J. Stanton Pierce、J. M. Salsbury、J. M. Fredericksen

  DOI：10.1021/ja01259a062

  日期：1942.7
• The Synthesis of Some Alkamine Esters of Alkylthiobenzoic Acids
  作者：John J. Donleavy、James English

  DOI：10.1021/ja01858a063

  日期：1940.1
• Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives
  作者：Zoran Ratković、Slađana B. Novaković、Goran A. Bogdanović、Dejan Šegan、Rastko D. Vukićević

  DOI：10.1016/j.poly.2010.04.034

  日期：2010.7

  (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel–Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds were characterized by spectroscopic data (UV, IR, 1H and 13C NMR), whereas their electrochemical properties have been investigated by cyclic voltammetry. The single-crystal X-ray structure determinations

  一锅法合成了七种新的（2-烷基硫代苯甲酰基）二茂铁，这是通过将二茂铁与相应的羧酸和三氯化磷原位生成的酰氯进行Friedel-Crafts酰化反应而实现的。所得化合物通过光谱数据（UV，IR，1 H和13NMR），而其电化学性质已通过循环伏安法研究。还报告了其中三个的单晶X射线结构测定。这三种衍生物均表现出分子内C–H…O相互作用，其中涉及环戊二烯基（Cp）环的供体和羰基氧作为受体。这种相互作用有利于两个部分的共面排列。符合C–O键的向量与相应的Cp平面之间的夹角均小于6.4°。常规的氢键在这三个晶体结构中都不存在，但是已经发现并详细分析了某些类型的C–H…O，C–H…S和C–H…π类型的弱分子间相互作用。