4-propylthio benzoic acid | 22683-48-3

• 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: 4-propylthio benzoic acid
• 英文别名: 4-(Propylsulfanyl)benzoic acid；4-propylsulfanylbenzoic acid
• CAS: 22683-48-3
• 化学式: C₁₀H₁₂O₂S
• mdl: MFCD09737860
• 分子量: 196.27
• InChiKey: BKWLRLMBMBHNJG-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C(Solv: ethanol (64-17-5))
• 沸点：
  341.6±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-propylthio benzoic acid 生成 N'-((2RS,3R)-3-amino-2-hydroxy-5-(isopropylsulfanyl)pentanoyl)-4-(propylsulfanyl)benzohydrazide
  参考文献：
  名称：

  Hydrazide and alkoxyamide angiogenesis inhibitors

  摘要：

  具有以下化学式的化合物是蛋氨酸氨肽酶2型（MetAP2）抑制剂，对抑制血管生成有用。还公开了抑制MetAP2的组合物和在哺乳动物中抑制血管生成的方法。

  公开号：

  US20020002152A1
• 作为产物：
  描述：

  4-(propylthio)benzonitrile 在 氢氧化钾 作用下， 生成 4-propylthio benzoic acid
  参考文献：
  名称：

  Buu-Hoi; Lecocq, Bulletin de la Societe Chimique de France, 1946, p. 475

  摘要：

  DOI：

文献信息

• Pyridyl inhibitors of hedgehog signalling
  申请人：Gunzner L. Janet

  公开号：US20060063779A1

  公开（公告）日：2006-03-23

  The invention provides novel inhibitors of hedgehog signaling that are useful as a therapeutic agents for treating malignancies where the compounds have the general formula I: wherein A, X, Y R 1 , R 2 , R 3 , R 4 , m and n are as described herein.

  这项发明提供了一种新型的刺刺信号抑制剂，可用作治疗恶性肿瘤的治疗剂，其中化合物具有一般式I： 其中A、X、Y、R1、R2、R3、R4、m和n如本文所述。
• 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。
• Thioetherification via Photoredox/Nickel Dual Catalysis
  作者：Matthieu Jouffroy、Christopher B. Kelly、Gary A. Molander

  DOI：10.1021/acs.orglett.6b00208

  日期：2016.2.19

  Hypervalent alkylsilicates represent new and readily accessible precursors for the generation of alkyl radicals under photoredox conditions. Alkyl radicals generated from such silicates serve as effective hydrogen atom abstractors from thiols, furnishing thiyl radicals. The reactive sulfur species generated in this manner can be funneled into a nickel-mediated cross-coupling cycle employing aromatic

  高价烷基硅酸盐代表了在光氧化还原条件下产生烷基自由基的新的和易于获得的前体。由这种硅酸盐产生的烷基自由基可作为有效的氢原子从硫醇中提取出氢原子，从而提供了噻吩基。可以将以这种方式产生的反应性硫物质漏入镍介导的交叉偶联循环中，该循环使用芳族溴化物提供硫醚。描述了该反应的偶然发现及其用于将各种芳族硫醇与各种芳基和杂芳基溴化物进行硫醚化的过程。S–H选择性H原子抽象事件使宽泛的官能团（包括带有质子部分的官能团）能够被耐受。
• Hydrogen bonding liquid crystalline benzoic acids with alkylthio groups: phase transition behavior and insights into the cybotactic nematic phase
  作者：Yuki Arakawa、Yukito Sasaki、Kazunobu Igawa、Hideto Tsuji

  DOI：10.1039/c7nj00282c

  日期：——

  A simple but novel class of hydrogen bonding liquid crystalline benzoic acids with alkylthio (or alkylsulfanyl; SR) groups was established. In general, although it is difficult for laterally non-substituted rod-like molecules with an alkylthio group to form some mesophases, the present molecules exclusively form a nematic (N) regime, owing to spontaneous carboxylic dimerization. It was found that the

  建立了具有烷硫基（或烷基硫烷基； SR）基团的氢键键合液晶苯甲酸的简单但新颖的一类。通常，尽管具有烷硫基的侧向非取代的棒状分子难以形成一些中间相，但是由于自发的羧酸二聚作用，本发明的分子仅形成向列（N）方案。研究发现，烷硫基中的碳原子数与转变温度以及生线稳定性密切相关：奇偶效应。尽管几乎所有奇数成员均不显示或仅表现出单向性更窄的偶数，偶数成员显示出更宽的单向性和对映N相。有趣的是，它们的热转变温度低于烷氧基（OR）类似物的温度，由于C–S–C键的角度较小（或弯曲较大），以及由于烷硫基的弱电子给体性质，其芳环上的电子密度低。另外，深入的广角X射线衍射测量表明，与N相比，烷硫基类似物表现出在N态（或Ncyb相）形成的近晶簇显着增强，并且簇类型接近于近晶（Sm）A。表现出清晰的SmC型簇的烷氧基类似物。结果表明，烷硫基进入介晶基团的强大的S⋯S分子间相互作用影响了Ncyb相中近晶簇的类型。深入的
• PYRIDYL INHIBITORS OF HEDGEHOG SIGNALLING
  申请人：GUNZNER Janet L.

  公开号：US20110092461A1

  公开（公告）日：2011-04-21

  The invention provides novel inhibitors of hedgehog signaling that are useful as a therapeutic agents for treating malignancies where the compounds have the general formula I: wherein A, X, Y R 1 , R 2 , R 3 , R 4 , m and n are as described herein.

  本发明提供了新型的刺猬信号抑制剂，可用作治疗恶性肿瘤的治疗剂，其中化合物具有一般式I：其中A、X、Y、R1、R2、R3、R4、m和n如本文所述。