5-甲基二硫杂环戊烯-3-硫酮 | 3354-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 中文名称: 5-甲基二硫杂环戊烯-3-硫酮
• 英文名称: 5-methyl-[1,2]dithiole-3-thione
• 英文别名: 5-methyl-3H-1,2-dithiole-3-thione；3H-1,2-Dithiole-3-thione, 5-methyl-；5-methyldithiole-3-thione
• CAS: 3354-40-3
• 化学式: C₄H₄S₃
• 分子量: 148.274
• InChiKey: LEPDMIYUICCABX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  5-甲基二硫杂环戊烯-3-硫酮 生成 5-[(E)-2-(4-tert-butylphenyl)ethenyl]dithiole-3-thione
  参考文献：
  名称：

  YAMAMOTO, ITARU;MATSUBARA, AKIRA;TOMIYA, KANDZI;MIDZUNO, OSAMU

  摘要：

  DOI：
• 作为产物：
  描述：

  3-oxo-butane dithionic acid. 在 咪唑 、 N-氯代丁二酰亚胺 、 双(三甲基硫化硅) 作用下， 生成 5-甲基二硫杂环戊烯-3-硫酮
  参考文献：
  名称：

  Synthesis of 3H-1,2-dithiole-3-thiones by a novel oxidative cyclization

  摘要：

  Reaction of 3-oxo dithioic acids with a combination of hexamethyldisilathiane and N-chlorosuccinimide in the presence of a catalytic amount of imidazole brings about oxidative ring closure to 3H-1,2-dithiole-3-thiones. Yields vary from poor to good.

  DOI：

  10.1016/s0040-4039(00)79295-1

文献信息

• Thionation with the Reagent Combination of Phosphorus Pentasulfide and Hexamethyldisiloxane
  作者：Thomas J. Curphey

  DOI：10.1021/jo0256742

  日期：2002.9.1

  The combination of P4S10 and hexamethyldisiloxane efficiently converts esters, lactones, amides, lactams, and ketones to their corresponding thiono derivatives. In the presence of elemental sulfur, 3-oxoesters are converted to dithiolethiones by this reagent. Yields are comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts

  P4S10和六甲基二硅氧烷的组合可将酯，内酯，酰胺，内酰胺和酮有效地转化为其相应的硫代衍生物。在元素硫的存在下，该试剂将3-氧代酯转化为二硫代硫酮。产率与使用劳森试剂获得的产率相当或更高。该方法的优点在于，可以通过简单的水解后处理或通过硅胶过滤而不是通过劳氏试剂所要求的色谱法来除去试剂衍生的副产物。
• Anethole dithiolethione and other dithiolethiones for the treatment of conditions associated with dysfunction of monoamine neruotransmission
  申请人：Drukarch Benjamin

  公开号：US20060194971A1

  公开（公告）日：2006-08-31

  The present disclosure relates to dithiolethione derivatives as monoamino oxidase inhibitors, in particular MAO-B inhibitors, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said dithiolethiones derivatives. The present disclosure also relates to the use of a compound disclosed herein for the manufacture of a medicament giving a beneficial effect. In embodiments of the present disclosure specific compounds disclosed herein are used for the manufacture of a medicament useful in the treatment, amelioration or prevention of conditions associated with dysfunction of monoamine neurotransmission. The compounds have the general formula (1) wherein the symbols have the meanings given in the specification.

  本公开涉及二硫乙酮衍生物作为单胺氧化酶抑制剂，特别是MAO-B抑制剂，以及用于制备这些化合物的方法和用于合成所述二硫乙酮衍生物的新颖中间体。本公开还涉及使用本公开披露的化合物制造具有有益效果的药物。在本公开实施例中，特定披露的化合物被用于制造用于治疗、改善或预防与单胺神经递质功能障碍相关的疾病的药物。这些化合物具有一般公式（1），其中符号具有规范中给定的含义。
• Sulfur-Containing Heterocycles Derived by Reaction of ?-Keto Amides withLawesson's Reagent
  作者：Takehiko Nishio

  DOI：10.1002/hlca.19980810531

  日期：——

  The reaction of ω-keto amides with Lawesson's reagent (LR: 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) is described. Treatment of 3-keto amides (2-acylacetamides) 1 with LR gave the corresponding 3-keto thioamides 2, along with 1,2-dithiole-3-thiones 3. Treatment of 4-keto amides, 3-acyl propionamides 5, with LR yielded five-membered heterocycles, pyrroles 6 and/or 2-aminothiophenes

  描述了ω-酮酰胺与Lawesson试剂（LR：2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二膦烷2,4-二硫键）的反应。用LR处理3-酮酰胺（2-酰基乙酰胺）1得到相应的3-酮硫酰胺2，以及1,2-二硫代-3-硫酮3。用LR处理4-酮酰胺，3-酰基丙酰胺5，得到五元杂环，吡咯6和/或2-氨基噻吩7。5-酮基酰胺，3-苯甲酰基丁酰胺8与LR反应生成二氢噻喃-2-硫酮9作为唯一产品​​，但收率低。2-酰基苯甲酰胺10也与LR反应，得到3-巯基异吲哚啉-2-酮11或二氢异苯并噻吩-1-硫酮12。
• Alkynyl Fischer carbene complex as a traceless directing group for the regioselective cycloaddition of dithiolethiones to arylacetylene: synthesis of E-dithiafulvene thione and dithioesters
  作者：Alejandro M. Granados、Alejandro M. Fracaroli、Rita H. de Rossi、Pedro Fuertes、Tomás Torroba

  DOI：10.1039/b715857b

  日期：——

  A phenylethynyl Fischer carbene complex was used as a traceless directing group for the regioselective cycloaddition of dithiolethiones to arylacetylene, which constitutes the first synthesis of E-dithiafulvene thione or dithioesters.

  苯乙炔基菲舍尔卡宾络合物用作二硫代硫酮与芳基乙炔的区域选择性环加成反应的无痕导向基团，这是E-二硫富富烯硫酮或二硫代酯的首次合成。
• Immunomodulator 1,2-dithiol-3-thione derivative composition, use method
  申请人：Mitsui Toatsu Chemicals Inc.

  公开号：US04760078A1

  公开（公告）日：1988-07-26

  A novel 1,2-dithiol-3-thione derivative which has an immunomodulating property, which is expressed by the formula (I): ##STR1## wherein R denotes hydrogen, halogen, lower alkoxy group, lower alkyl group, amino group, lower alkyl-substituted amino group or lower alkoxycarbonyl group.

  一种具有免疫调节性质的新型1,2-二硫代-3-硫醇衍生物，其化学式为(I)：##STR1## 其中R表示氢、卤素、低级烷氧基、低级烷基、氨基、低级烷基取代的氨基或低级烷氧羰基基团。

表征谱图