1,4-dihydroxy-9H-thioxanthen-9-one | 14992-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 1,4-dihydroxy-9H-thioxanthen-9-one
• 英文别名: 1,4-dihydroxythioxanthene-9-one；1,4-dihydroxythioxanthen-9-one；1,4-dihydroxythioxanthone；1,4-dihydroxy-thioxanthen-9-one；1,4-Dihydroxy-thioxanthen-9-on
• CAS: 14992-80-4
• 化学式: C₁₃H₈O₃S
• 分子量: 244.271
• InChiKey: ROPLCNKLLVUPHM-UHFFFAOYSA-N

物化性质

• 熔点：
  289 °C(Solv: ethanol (64-17-5))
• 沸点：
  452.1±45.0 °C(Predicted)
• 密度：
  1.537±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dihydroxy-9H-thioxanthen-9-one 在 氯化亚砜 作用下， 反应 2.0h， 以64%的产率得到2,3-dichloro-1,4-dihydro-9H-thioxanthene-1,4,9-trione
  参考文献：
  名称：

  Syntesis of 2- and 3-chloro-1,4-dihydroxythioxanthen-9-ones

  摘要：

  1,4-dihydroxythioxanthen-9-one was for the first time subjected to regioselective chlorination into 2-chloro-1,4-dihydroxythioxanthen-9-one effected by SOCl(2) at room temperature. The hydrochlorination of thioxanthen-1,4,9-trione led to the formation of 2- and 3-chloro-1,4-dihydroxythioxanthene-9-ones with the 3-isomer prevailing.

  DOI：

  10.1134/s1070428010020168
• 作为产物：
  描述：

  2, 2'-二硫代二苯甲酸 在 硫酸 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 1,4-dihydroxy-9H-thioxanthen-9-one
  参考文献：
  名称：

  Singh, Pahup; Pardasani, R. T.; Prashant, Anita, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 86, # 1.4, p. 21 - 26

  摘要：

  DOI：

文献信息

• Reaction of thiosalicylic acid with 1,4-quinones and cyclization of the resulting arylsulfanylbenzoic acids
  作者：V. A. Loskutov、I. V. Beregovaya

  DOI：10.1134/s1070428009090152

  日期：2009.9

  Thiosalicylic acid reacts with 1,4-benzoquinone to give 2-(1,4-dihydroxyphenylsulfanyl)benzoic acid which undergoes intramolecular cyclization to 1,4-dihydroxythioxanthen-9-one in the presence of dehydrating agents. Cyclization of arylsulfanylbenzoic acids obtained by reaction of thiosalicylic acid with 1,4-naphtho- and anthraquinones leads to 1,4-quinone derivatives, benzo- and naphthothioxanthenetriones

  硫代水杨酸与1,4-苯醌反应生成2-（1,4-二羟基苯基硫烷基）苯甲酸，在脱水剂的存在下，将其分子内环化为1,4-二羟基噻吨-9。通过硫代水杨酸与1，4-萘醌和蒽醌反应获得的芳基硫烷基苯甲酸的环化产生1，4-醌衍生物，苯并噻吩和萘并噻吨蒽酮。
• A Green and Regioselsctive Synthesis of Xanthone and Thioxanthone Derivatives in the Presence of Heteropoly Acid Under Microwave Irradiation
  作者：Mohammad Nasseri、Somayyeh Alizadeh、Batol Zakerinasb、Alireza Beni

  DOI：10.2174/1570178610666131231000006

  日期：2014.4

  One-pot preparation of a variety of pharmacologically pertinent xanthone heterocycles has efficiently been achieved from their respective phenol compounds and salicylic acid/ thiosalicylic acid in the presence of the catalytic amount of heteropoly acid. Most of the reactions showed high regioselectivity and produced xanthones/ thioxanthones in good yields under microwave irradiation.

  在催化量的杂多酸存在下，由它们各自的酚类化合物和水杨酸/硫代水杨酸有效地实现了多种药理学上相关的黄酮酮杂环的一锅制备。大多数反应在微波辐射下显示出高的区域选择性，并以良好的产率产生了ant吨/噻吨酮。
• Ruthenium-catalyzed C–H activation of thioxanthones
  作者：Danny Wagner、Stefan Bräse

  DOI：10.3762/bjoc.11.49

  日期：——

  Thioxanthones - being readily available in one step from thiosalicylic acid and arenes - were used in ruthenium-catalyzed C-H-activation reaction to produce 1-mono- or 1,8-disubstituted thioxanthones in good to excellent yields. Scope and limitation of this reaction are presented.

  噻吨酮（可通过硫代水杨酸和芳烃一步获得）用于钌催化的 CH 活化反应，以良好至优异的产率生产 1-单取代或 1,8-二取代的噻吨酮。介绍了该反应的范围和局限性。
• A Novel and Efficient Method for the Synthesis of New Hydroxythioxanthone Derivatives
  作者：Hashem Sharghi、Ali Beni

  DOI：10.1055/s-2004-831253

  日期：——

  We describe the synthesis of some new hydroxythioxanthones by treatment of thiosalicylic acid (TSA) with various substituted phenols in the presence of Al2O3-CH3SO3H (AMA). Most of the reactions show high regioselectivity and produce thioxanthones in good yields.

  我们描述了一些新羟基噻喱酮的合成方法，采用了在Al2O3-CH3SO3H（AMA）存在下，用各种取代酚处理噻唑酸（TSA）。大多数反应表现出高的区位选择性，并良好地产出了噻喱酮。
• HIGH SPECIFICITY ANTICANCER PHARMACOLOGICAL DRUG SYSTEM, DRUG SYNTHESIS, AND DRUG DEVELOPMENT PROCESS
  申请人：——

  公开号：US20040116508A1

  公开（公告）日：2004-06-17

  A process for producing new anticancer drugs such that the drugs can be administered in a nontoxic, proto-drug form and, subsequent to a time delay which allows for differential concentration in the target cancer or invasive tissues or cells, the non-toxic drug is then modified by an activation drug to selectively provide toxic levels of a pharmacologically active agent to the target issue.

  一种生产新的抗癌药物的过程，使得这些药物可以以无毒的原药形式给予，并在经过一段时间延迟后，允许在目标癌症或侵袭性组织或细胞中产生差异浓度，然后通过激活药物修改非毒性药物，以选择性地提供目标组织的药理活性剂的毒性水平。