5-chloro-2-hydroxybenzenethiol | 21151-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 5-chloro-2-hydroxybenzenethiol
• 英文别名: 4-Chloro-2-mercaptophenol；5-Chlor-2-hydroxy-thiophenol；4-Chlor-2-mercaptophenol；2-Hydroxy-5-chlorothiophenol；4-chloro-2-sulfanylphenol
• CAS: 21151-77-9
• 化学式: C₆H₅ClOS
• 分子量: 160.624
• InChiKey: GUFXPBBJWWWAAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-hydroxybenzenethiol 在 吡啶 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 16.0h， 生成 7-chloro-3-hydroxy-1,5-benzoxathiepine
  参考文献：
  名称：

  Cabiddu, Salvatore; Melis, Stefana; Sotgiu, Francesca, Phosphorus and Sulfur and the Related Elements, 1982, vol. 14, p. 151 - 156

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-2-氨基苯酚 生成 5-chloro-2-hydroxybenzenethiol
  参考文献：
  名称：

  Cabiddu,S. et al., Gazzetta Chimica Italiana, 1969, vol. 99, p. 397 - 410

  摘要：

  DOI：

文献信息

• Regioselective copper(I)-catalyzed C–H hydroxylation/C–S coupling: expedient construction of 2-(styrylthio)phenols
  作者：Run-Sheng Xu、Lei Yue、Yuan-Jiang Pan

  DOI：10.1016/j.tet.2012.04.048

  日期：2012.6

  Regioselective copper(I)-catalyzed C–H hydroxylation/C–S coupling of aryl thiols with vinyl halides was developed. Starting from substituted aryl thiols and vinyl halides, various 2-(styrylthio)phenol derivatives were efficiently prepared. The application of the synthetic methodology to generate the bioactive organic intermediate was also exemplified.

  开发了区域选择性铜（I）催化的芳基硫醇与乙烯基卤化物的CH羟基羟基化/ CS偶联。从取代的芳基硫醇和卤代乙烯开始，可以有效地制备各种2-（苯乙烯基硫代）苯酚衍生物。还举例说明了合成方法用于产生生物活性有机中间体的应用。
• 1,5-Benzoxathiepin derivatives. I. Synthesis and reaction of 1,5-benzoxathiepin derivatives.
  作者：HIROSADA SUGIHARA、HIROSHI MABUCHI、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.35.1919

  日期：——

  Methyl 3-oxo-3, 4-dihydro-2H-1, 5-benzoxathiepin-4-carboxylates (3a-f) were synthesized by regioselective Dieckmann reaction of methyl 2-methoxycarbonylmethylthiophenoxyacetates (2a-f) [readily prepared from 2-mercaptophenols (la-f)] in fairly good yields. Alkylation of thc ketoester (3b) with alkyl halides gave 4-alkylated derivatives (7 and 8). A substituent at the 2-position on the 1, 5-benzoxathiepin ring was introduced by Dieckmann reaction of methyl ssubstituted 2-methoxycarbonylmethylthiophenoxyacetates (11, 12b and 12f). Thorpe-Ziegler reaction of 2-cyanomethylthiophenoxyacetonitriles (18a-d) gave 3-amino-2H-1, 5-benzoxathiepin-4-carbonitriles (19a-d). Novel heterocycles, 4-amino-11H-pyrimido [4, 5-c] [1, 5] benzoxathiepin derivatives (24-32), were synthesized by the reaction of enaminonitriles (3a and 3b) with amidines or guanidines.

  甲基3-氧基-3, 4-二氢-2H-1, 5-苯并噻噁烯-4-羧酸酯（3a-f）通过区域选择性的Dieckmann反应合成，起始物为甲基2-甲氧基羧基甲基噻吩氧乙酸酯（2a-f，易于由2-巯基苯酚（1a-f）制备而成），产率相当不错。对酮酸酯（3b）进行烷基化反应，使用烷基卤化物得到了4-烷基化衍生物（7和8）。通过对甲基取代的2-甲氧基羧基甲基噻吩氧乙酸酯（11, 12b和12f）进行Dieckmann反应，实现了在1, 5-苯并噻噁烯环的2位引入取代基。对2-氰甲基噻吩氧乙腈（18a-d）进行Thorpe-Ziegler反应，得到3-胺基-2H-1, 5-苯并噻噁烯-4-氰基（19a-d）。通过酰胺腈（3a和3b）与酰胺或胍反应，合成了新型杂环化合物4-氨基-11H-吡咯并[4, 5-c][1, 5]苯并噻噁烯衍生物（24-32）。
• 1,5-benzoxathiepin derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04672064A1

  公开（公告）日：1987-06-09

  Novel 1,5-benzoxathiepin derivatives of the formula: ##STR1## [wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, hydroxy, lower alkyl or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen, optionally substituted lower alkyl or optionally substituted cycloalkyl or optionally substituted aralkyl, or both jointly form an optionally substituted ring together with the adjacent nitrogen atom; X is hydrogen, optionally substituted lower alkyl, optionally substituted aryl or a carboxyl group which may be esterified or amidated; Y is ##STR2## (wherein R.sub.5 is hydrogen, acyl or optionally substituted carbamoyl); m is an integer of 0 to 2; n is an integer of 1 to 6] and salts thereof exhibit serotonin S.sub.2 receptor blocking activity, calcium antagonism, actions to relieve cerebral vasospasm and to improve renal circulation and diuretic and antithrombotic activities, and are of value as a prophylactic and therapeutic agent for ischemic cardiopathies, thrombosis, hypertension and cerebral circulatory disorders.

  1,5-苯并噻吩衍生物的新颖化合物的化学式为：##STR1##[其中R.sub.1和R.sub.2分别是氢、卤素、羟基、低烷基或低烷氧基；R.sub.3和R.sub.4分别是氢、可选择取代的低烷基、可选择取代的环烷基或可选择取代的芳基，或者共同与相邻氮原子形成可选择取代的环的；X是氢、可选择取代的低烷基、可选择取代的芳基或可能酯化或酰胺化的羧基；Y是##STR2##(其中R.sub.5是氢、酰基或可选择取代的氨基酰)；m是0到2的整数；n是1到6的整数]及其盐具有血清素S.sub.2受体阻滞活性、钙拮抗作用、缓解脑血管痉挛、改善肾循环和利尿和抗血栓活性，并且对于缺血性心脏病、血栓形成、高血压和脑循环障碍等疾病具有预防和治疗作用。
• Foundry aggregate binder compositions and their use
  申请人：OCCIDENTAL CHEMICAL CORPORATION

  公开号：EP0040497A1

  公开（公告）日：1981-11-25

  Resin binder compositions for foundry sand molds and cores which comprise a solution in an inert solvent of a polyol component comprising a phenol-ketone orthiophenol-ketone resin and an organic polyisocyanate, optionally with a reactive solvent and a cross-linking agent. The binder composition cures rapidly at ambient temperature in the presence of a tertiary amine curing agent to provide strong foundry molds or cores. Polyether polyols may also be incorporated in the polyol component of the binder composition.

  用于铸造砂模和型芯的树脂粘结剂组合物，它包括多元醇组分在惰性溶剂中的溶液，多元醇组分包括苯酚-酮邻苯酚-酮树脂和有机多异氰酸酯，可选择使用活性溶剂和交联剂。粘合剂成分在叔胺固化剂的作用下，可在环境温度下快速固化，从而提供坚固的铸造模具或芯模。粘合剂组合物的多元醇成分中还可加入聚醚多元醇。
• Selective Dealkylation of Alkyl Aryl Sulfides
  作者：S. Cabiddu、S. Melis、P. P. Piras、F. Sotgiu

  DOI：10.1055/s-1982-29868

  日期：——