2,4-dicyano-3-amino-5-methylthiothiophene | 116255-96-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,4-dicyano-3-amino-5-methylthiothiophene
• 英文别名: 3-amino-2,4-dicyano-5-methylthiothiophene；2-methylthio-3,5-dicyano-4-aminothiophene；3-amino-5-methylsulfanylthiophene-2,4-dicarbonitrile
• CAS: 116255-96-0
• 化学式: C₇H₅N₃S₂
• 分子量: 195.269
• InChiKey: XKPNQVGLLYSYFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 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：
  127
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-dicyano-3-amino-5-methylthiothiophene 在 盐酸 、 间氯过氧苯甲酸 、 copper(l) chloride 、 sodium chloride 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 3-chloro-2,4-dicyano-5-methylsulfinylthiophene
  参考文献：
  名称：

  2-（烷硫基）-和2-（芳硫基）-3-氰基噻吩的合成。烷基亚硫基被硫醇的亲核取代。

  摘要：

  活化的2-（烷基亚磺酰基）噻吩被烷基或芳基硫醇的亲核取代得到相应的2-（烷硫基）-或2-（芳硫基）-取代的噻吩。当使用硫醇根阴离子代替硫醇根时，亚砜还原是主要反应。

  DOI：

  10.1016/s0040-4020(01)81450-2
• 作为产物：
  描述：

  Thieno(2,3-c)isothiazole-5-carbonitrile, 4-amino-3-(methylthio)- 以 乙醇 为溶剂， 反应 48.0h， 生成 2,4-dicyano-3-amino-5-methylthiothiophene
  参考文献：
  名称：

  Corsaro, Antonino; Guerrera, Francesco; Sarva, Maria C., Heterocycles, 1988, vol. 27, # 10, p. 2539 - 2544

  摘要：

  DOI：

文献信息

• Thio compounds having fungicidal activity
  申请人：Duphar International Research B.V.

  公开号：US04994485A1

  公开（公告）日：1991-02-19

  The invention relates to new thio compounds of the general formula ##STR1## wherein R is an alkyl group substituted or not substituted with halogen and having 1-12 carbon atoms, an alkenyl or alkynyl group having 2-4 carbon atoms, an alkadienyl group having 3 or 4 carbon atoms or a substituted or unsubstituted phenyl or phenyl(C.sub.1 -C.sub.4)alkyl group; R.sub.1 is a cyano group, a formyl group, an alkylcarbonyl or alkoxycarbonyl group substituted or unsubstituted with halogen and having 2-5 carbon atoms, a substituted or unsubstituted benzoyl group, or an alkylsulphonyl group having 1-4 carbon atoms; R.sub.2 is a hydrogen atom, a halogen atom, an amino group unsubstituted or substituted with one or two groups selected from C.sub.1 -C.sub.4 alkyl and C.sub.2 -C.sub.5 alkylcarbonyl, an amino group forming part of a heterocyclic ring which may comprise 1 or 2 additional heteroatoms selected from N, O and S, an alkyl or alkoxy group having 1-4 carbon atoms and optionally substituted with C.sub.2 -C.sub.5 alkylcarbonyl, or a substituted or unsubstituted phenyl, phenoxy or phenylthio group; or wherein R.sub.1 and R.sub.2, together with the vinylene group to which they are bound, constitute a substituted or unsubstituted phenyl group; X is a cyano group or a formyl group; n is 1 or 2; Y is an alkylthio group having 1-4 carbon atoms; and Z is a hydrogen atom, a halogen atom, a nitro group, or an alkyl or alkoxy group having 1-4 carbon atoms and optionally substituted with halogen; or wherein Y and Z together constitute a sulphur atom; with the proviso that, when Y and Z do not together constitute a sulphur atom, R.sub.1 and R.sub.2, together with the vinylene group to which they are bound, constitute a substituted or unsubstituted phenyl group. The new compounds show a fungicidal and/or bactericidal activity and may be used in particular against plantpathogenic seed fungi and soil fungi and/or bacteria.

  本发明涉及一种新的硫代化合物，其通式为##STR1##其中，R是烷基，可以被卤素取代或不取代，具有1-12个碳原子，烯基或炔基，具有2-4个碳原子，烷二烯基，具有3或4个碳原子，或取代或未取代的苯基或苯基（C.sub.1-C.sub.4）烷基；R.sub.1是氰基，甲酰基，取代或未取代的烷基羰基或烷氧羰基，具有2-5个碳原子，取代或未取代的苯甲酰基，或具有1-4个碳原子的烷基磺酰基；R.sub.2是氢原子，卤素原子，未取代或取代了C.sub.1-C.sub.4烷基和C.sub.2-C.sub.5烷基羰基中的一种或两种基团的氨基，是杂环环中的氨基，该杂环可以包含1或2个额外的杂原子，选自N、O和S，具有1-4个碳原子的烷基或烷氧基，可以选用C.sub.2-C.sub.5烷基羰基进行取代，或取代或未取代的苯基，苯氧基或苯硫基；或者R.sub.1和R.sub.2与它们所连接的乙烯基组成取代或未取代的苯基；X是氰基或甲酰基；n为1或2；Y是具有1-4个碳原子的烷基硫基；Z是氢原子，卤素原子，硝基或具有1-4个碳原子的烷基或烷氧基，可以选用卤素进行取代；或者Y和Z一起构成硫原子；条件是当Y和Z不构成硫原子时，R.sub.1和R.sub.2与它们所连接的乙烯基组成取代或未取代的苯基。这些新化合物表现出杀真菌和/或杀菌作用，特别适用于对植物病原菌和土壤真菌和/或细菌的防治。
• New thio compounds having fungicidal activity
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0234622A1

  公开（公告）日：1987-09-02

  The invention relates to new thio compounds of the general formula wherein R is an alkyl group substituted or not substituted with halogen and having 1-12 carbon atoms, an alkenyl or alkynyl group having 2-4 carbon atoms, an alkadienyl group having 3 or 4 carbon atoms or a substituted or unsubstituted phenyl or phenyl(C1-C4)alkyl group; R, is a cyano group, a formyl group, an alkylcarbonyl or alkoxycarbonyl group substituted or unsubstituted with halogen and having 2-5 carbon atoms, a substituted or unsubstituted benzoyl group, or an alkylsulphonyl group having 1-4 carbon atoms; R2 is a hydrogen atom, a halogen atom, an amino group unsubstituted or substituted with one or two group selected from C1-C4 alkyl and C2-C5 alkylcarbonyl, an amino group forming part of a heterocyclic ring which may comprise 1 or 2 additional heteroatoms selected from N, 0 and S, an alkyl or alkoxy group having 1-4 carbon atoms and optionally substituted with C2-C5 alkylcarbonyl, or a substituted or unsubstituted phenyl, phenoxy or phenylthio group; or wherein R, and Rz, together with the vinylene group to which they are bound, constitute a substituted or unsubstituted phenyl group; X is a cyano group or a formyl group; n is 1 or 2; Y is an alkylthio group having 1-4 carbon atoms; and Z is a hydrogen atom, a halogen atom, a nitro group, or an alkyl or alkoxy group having 1-4 carbon atoms and optionally substituted with halogen; or wherein Y and Z together constitute a sulphur atom; with the proviso that, when Y and Z do not together constitute a sulphur atom, R1 and Rz, together with the vinylene group to which they are bound, constitute a substituted or unsubstituted phenyl group. The new compounds show a fungicidal and/or bactericidal activity and may be used in particular against plantpathogenic seed fungi and soil fungi and/or bacteria.

  本发明涉及通式如下的新硫代化合物 式中 R 是被卤素取代或未被卤素取代且具有 1-12 个碳原子的烷基、具有 2-4 个碳原子的烯基或炔基、具有 3 或 4 个碳原子的烷二烯基或被取代或未被取代的苯基或苯基（C1-C4）烷基； R，是氰基、甲酰基、被卤素取代或未被卤素取代且具有 2-5 个碳原子的烷基羰基或烷氧羰基、被取代或未被取代的苯甲酰基或具有 1-4 个碳原子的烷基磺酰基； R2 是氢原子、卤素原子、未取代的或被 1 个或 2 个选自 C1-C4 烷基和 C2-C5 烷基羰基取代的氨基、构成杂环一部分的氨基（该杂环可包括 1 个或 2 个选自 N、0 和 S 的额外杂原子）、具有 1-4 个碳原子且任选被 C2-C5 烷基羰基取代的烷基或烷氧基、或取代或未取代的苯基、苯氧基或苯硫基； 或 其中 R 和 Rz 与它们结合的乙烯基一起构成取代或未取代的苯基； X 是氰基或甲酰基； n 是 1 或 2； Y 是具有 1-4 个碳原子的烷硫基；以及 Z 是氢原子、卤素原子、硝基或具有 1-4 个碳原子并可选择被卤素取代的烷基或 烷氧基； 或其中 Y 和 Z 共同构成一个硫原子；但当 Y 和 Z 不共同构成一个硫原子时，R1 和 Rz 与它们所结合的乙烯基共同构成一个取代或未取代的苯基。 新化合物具有杀真菌和/或杀细菌的活性，尤其可用于防治植物病原性种子真菌和土壤真菌和/或细菌。
• 3-Amino-5-phenoxythiophenes:  Syntheses and Structure−Function Studies of a Novel Class of Inhibitors of Cellular <scp>l</scp>-Triiodothyronine Uptake
  作者：Detlef Briel、Dirk Pohlers、Mathias Uhlig、Silke Vieweg、Gerhard H. Scholz、Michael Thormann、Hans-Jörg Hofmann

  DOI：10.1021/jm980288r

  日期：1999.5.1

  A series of substituted 3-amino-5-phenoxythiophenes was synthesized starting from malodinitrile and carbon disulfide. The resulting dicyanoketenedithiolate reacts via Thorpe-Dieckmann cyclization with halogen methanes bearing electron-withdrawing groups to give thiophene-2-thiolates, which can be transformed into 3-amino-5-(methylsulfonyl)thiophene-4-carbonitriles. Replacement of the methylsulfonyl groups by substituted phenolates provides the substituted 3-amino-5-phenoxythiophenes. Some of the derivatives show a considerable inhibitory potency for the L-T-3 uptake in inhibition studies on human HepG2 hepatoma cells with maximum values of about 60% at a dose of 10(-5) M for the most potent 2-benzoyl derivatives. The structure of the phenoxythiophenes fits well into a general concept derived for other classes of L-T-3 uptake inhibitors, which postulates an angular and perpendicular orientation of the ring systems in these compounds as a prerequisite for an inhibitory potency. Docking studies for the phenoxythiophenes with transthyretin as a receptor model show their preferred attack at the L-T-4/L-T-3 binding channel.
• CORSARO, ANTONINO;GUERRERA, FRANCESCO;SARVA, MARIA C.;SIRACUSA, MARIA A., HETEROCYCLES, 27,(1988) N1, C. 2539-2544
  作者：CORSARO, ANTONINO、GUERRERA, FRANCESCO、SARVA, MARIA C.、SIRACUSA, MARIA A.

  DOI：——

  日期：——
• LUTEIJN, J. M.;DOLMAN, H.;WALS, H. C., TETRAHEDRON, 44,(1988) N 18, C. 5921-5928
  作者：LUTEIJN, J. M.、DOLMAN, H.、WALS, H. C.

  DOI：——

  日期：——