sodium 3-methoxy-benzenethiolate | 51679-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: sodium 3-methoxy-benzenethiolate
• 英文别名: sodium 3-methoxythiophenolate；Sodium 3-methoxybenzenethiolate；sodium;3-methoxybenzenethiolate
• CAS: 51679-08-4
• 化学式: C₇H₇OS*Na
• 分子量: 162.188
• InChiKey: QUTBTFOCPMQYDR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.39
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  10.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium 3-methoxy-benzenethiolate 在 sodium hydroxide 、 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.67h， 生成 (E)-3-(6-methoxy-3-pentylbenzo[b]thien-2-yl)-2-propenoic acid 4-nitrophenyl ester
  参考文献：
  名称：

  Propenyl carboxamide derivatives as antagonists of platelet-activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl] 3-substituted propenyl carboxamide derivatives bearing an unsaturated bicyclic moiety in the 3-position was prepared and evaluated for PAF (platelet activating factor) antagonist activity. These compounds represent conformationally constrained direct analogues of the corresponding potent 5-aryl-pentadienecarboxamides (5). Most of the new compounds were active in a PAF-binding assay employing whole, washed dog platelets as the receptor source and inhibited PAF-induced bronchoconstriction in guinea pigs after intravenous administration. However, oral activity in the PAF-induced bronchoconstriction model was highly sensitive to the nature and substitution of the bicyclic ring system. The most interesting compounds included [R-(E)]-(1-butyl-6-methoxy-2-naphthyl)-N-[1-methyl-4-(3- pyridinyl)butyl]-2-propenamide (4b), [R-(E)]-(3-butyl-6-methoxy-2- benzo[b]thiophene-yl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide (4k), and [R-(E)]-(3-butyl-6-methoxy-1-methyl-2-indoly)-N-[1-ethyl-4- (3-pyridinyl)butyl]-2-propenamide (4l) which inhibited PAF-induced broncho-constriction in guinea pigs with IC50s of 3.0-5.4 mg/kg, when the animals were challenged 2 h after drug treatment. They were also highly effective 6 h after a 50 mg/kg oral dose. This study supports the notion that the key remote aromatic ring present in the 5-arylpentadienecarboxamides (5) is preferentially coplanar with the diene system for good PAF antagonist activity.

  DOI：

  10.1021/jm00172a029
• 作为产物：
  描述：

  3-甲氧基苯硫酚 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 sodium 3-methoxy-benzenethiolate
  参考文献：
  名称：

  Biaromatic compounds and pharmaceutical and cosmetic compositions comprising them

  摘要：

  由丙炔基或芳烃基键连接的双芳香族化合物，对应式（I）。

  公开号：

  US06346546B1

文献信息

• 2-[(Phenylthio)methyl]pyridine derivatives: new antiinflammatory agents
  作者：Fortuna Haviv、Robert W. DeNet、Raymond J. Michaels、James D. Ratajczyk、George W. Carter、Patrick R. Young

  DOI：10.1021/jm00356a018

  日期：1983.2

  2-[(Phenylthio)methyl]pyridine derivatives inhibited the dermal reverse passive Arthus reaction (RPAR) in the rat. In the same model, indomethacin was inactive, and hydrocortisone was active. Compounds Ia-d also significantly reduced exudate volume and white blood cell accumulation in the pleural RPAR. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin

  2-[（（苯硫基）甲基]吡啶衍生物可抑制大鼠皮肤逆向被动Arthus反应（RPAR）。在同一模型中，消炎痛是无活性的，氢化可的松是有活性的。化合物Ia-d还显着减少了胸膜RPAR中的渗出液量和白细胞积聚。这种活性模式与氢化可的松相似，与消炎痛不同。
• Sulfanyl-Substituted [3]Cumulenes and Buta-1,3-dienes from a Tetrakis(pyridinium)-Substituted Butadiene
  作者：Andreas Schmidt、Alireza Rahimi、Mimoza Gjikaj

  DOI：10.1055/s-0029-1216861

  日期：2009.7

  3-dienes, or tetrakis(sulfanyl)-substituted 2,3-dichlorobuta-1,3-dienes by reactions with thiolates or a sulfinate. The outcome of the reaction depends on the reaction conditions and the substitution pattern of the starting sulfur nucleophiles. dienes and trienes - sulfides - pyridines - perchlorinated compounds - persulfurated compounds

  用4-（N，N-二甲基氨基）吡啶处理过氯丁1,3-二烯导致1,1'，1''，1''-（2,3-dichlorobuta-1,3-二烯-1,1,4,4-四基）四[4-（二甲基氨基）吡啶]四氯化物（通过X射线分析确定的结构），将其转化为全硫化丁二烯（[3]枯草烯），五元（硫烷基）-通过与硫醇盐或亚磺酸盐的反应而取代的丁基-1,3-二烯或四（硫烷基）取代的2,3-二氯丁-1,3-二烯。反应的结果取决于反应条件和起始硫亲核试剂的取代方式。 二烯和三烯-硫化物-吡啶-高氯化合物-过硫化化合物
• Elimination–addition. Part XI. Electronic effects upon the reactivity of aryl vinyl sulphones towards amines
  作者：S. T. McDowell、C. J. M. Stirling

  DOI：10.1039/j29670000348

  日期：——

  Rates of addition of t-butylamine to a series of nuclear-substituted aryl vinyl sulphones have been measured for reactions in ethanol at 25°. The results are well correlated by the Hammett σρ relationship, the value of ρ=+1·59 being obtained with substituents possessing σ constants in the range –0·268 to +0·778. The reaction is compared with others which proceed via a carbanionic transition state.

  对于在乙醇中在25°下的反应，已经测量了叔丁胺向一系列核取代的芳基乙烯基砜中的加成率。通过Hammettσρ关系可以很好地关联结果，其中ρ= + 1·59的值是由具有介于–0·268至+ 0·778范围内的σ常数的取代基获得的。将反应与通过碳负离子过渡态进行的其他反应进行比较。
• Discovery and SAR development of 2-(phenylamino) imidazolines as postacyclin receptor antagonists
  作者：Robin D. Clark、Alam Jahangir、Daniel Severance、Rick Salazar、Thomas Chang、David Chang、Mary Frances Jett、Steven Smith、Keith Bley

  DOI：10.1016/j.bmcl.2003.10.070

  日期：2004.2

  On the basis of screening hits (1a,b), a series of selective, high affinity prostacyclin receptor antagonists was developed. The optimized lead compound 25d [(4,5-dihydro-1H-imidazol-2-yl)-[4-(4-isopropoxybenzyl)phenyl]amine] had analgesic activity in the rat.

  基于筛选结果（1a，b），开发了一系列选择性，高亲和力的前列环素受体拮抗剂。优化的铅化合物25d [（4,5-二氢-1H-咪唑-2-基）-[4-（4-异丙氧基苄基）苯基]胺]在大鼠中具有镇痛作用。
• One‐Pot Substitution‐Rearrangement Reaction of 2‐Chloroglycidic Ester: Effective Protocol for the Preparation of 3‐Arylsulfenyl‐2‐keto Ester
  作者：Takuzo Komiyama、Yutaka Takaguchi、Sadao Tsuboi

  DOI：10.1080/00397910500374914

  日期：2006.1

  Abstract The one‐pot substitution‐rearrangement reaction of 2‐chloroglycidic ester is reported. Treatment of 2‐chloroglycidic ester with sodium arylthiolate at room temperature results in the formation of 3‐arylsulfenyl‐2‐keto ester in excellent to good yields.

  摘要 报道了2-氯缩水甘油酯的一锅取代重排反应。在室温下用芳基硫醇钠处理 2-氯缩水甘油酯导致 3-芳基硫基-2-酮酯的形成，产率非常好。