5,6-dihydro-4-(3-thiono[1,2]dithiol-4-yl)-[1,2]dithiolo[3,4-b][1,4]thiazine-3-thione | 204758-35-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5,6-dihydro-4-(3-thiono[1,2]dithiol-4-yl)-[1,2]dithiolo[3,4-b][1,4]thiazine-3-thione
• 英文别名: 5,6-dihydro-4-(3-thiono[1,2]dithiol-4-yl)[1,2]dithiolo[3,4-b][1,4]thiazine-3-thione；4-(3-Sulfanylidenedithiol-4-yl)-5,6-dihydrodithiolo[3,4-b][1,4]thiazine-3-thione
• CAS: 204758-35-0
• 化学式: C₈H₅NS₇
• 分子量: 339.596
• InChiKey: YMPRJLUPPXRQIH-UHFFFAOYSA-N

物化性质

• 熔点：
  240-241 °C
• 沸点：
  497.810±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.905±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  194
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-4-(3-thiono[1,2]dithiol-4-yl)-[1,2]dithiolo[3,4-b][1,4]thiazine-3-thione 、 1,4-bis(2-thienyl)but-2-yne-1,4-dione 以 甲苯 为溶剂， 反应 1.0h， 以73%的产率得到3,4-di(2-thienoyl)-6-[5,6-di(2-thienoyl)-4-{spiro(4,5-di(2-thienoyl)-1,3-dithiol-2-yl)}-thiopyran-5-yl]-7,8-dihydro-5-[spiro(4,5-di(2-thienoyl)-1,3-dithiol-2-yl)]thiopyrano[2,3-b][1,4]thiazine
  参考文献：
  名称：

  [1,2]二硫代[1,4]噻嗪和[1,2]二硫代吡咯的级联环加成反应合成高度支化的硫氮杂环

  摘要：

  我们报告了通过级联环加成到容易获得的多环1,2-二硫代3-硫酮上的一些新的多硫-氮杂环的合成。因此，用乙炔二羧酸二甲酯（DMAD）或二苯甲酰基乙炔（DBA）处理双[1,2]二硫代吡咯并二硫酮1，得到1：4加合物2a，b和3a。另一方面，双[1,2]二硫代[1,4]噻嗪二硫酮4a - d与相同的双亲性化合物环加成后，可得到1：2、1：3或1：4加合物5a - c，6a，7a，8a，9a和10a，c，d有选择地以中等至高产。反应条件对于实现热反应的选择性至关重要。三氟甲磺酸scan的催化用于4a和2当量的DMAD的反应。的[1,2] dithiolo [1,4]噻嗪二硫酮治疗11具有DBA得到1：2,1：3（两种异构体），和1：4分的加合物12 - 14和15A - d选择性。所选实施例的循环伏安法显示出不可逆过程，不受与杂环系统键合的外围基团的影响。

  DOI：

  10.1021/jo035748p
• 作为产物：
  描述：

  N,N-二异丙基乙醇胺 在 二氯化二硫 、 diphosphorus pentasulfide 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以7%的产率得到5,6-dihydro-4-(3-thiono[1,2]dithiol-4-yl)-[1,2]dithiolo[3,4-b][1,4]thiazine-3-thione
  参考文献：
  名称：

  Synthesis of Bis[1,2]dithiolo[1,4]thiazines and a [1,2]Dithiolo[1,4]thiazine from Tertiary Diisopropylamines

  摘要：

  The reaction of N-(2-chloroethyl)diisopropylamine 1a with S2Cl2 allows the selective one-pot preparation of the tricyclic 4-(2-chloroethyl) bisdithiolothiazines 2-4 or, by addition of phosphorus pentasulfide at a rate stage in the reaction, of the dithiolothiazine 5. The chloroethyl derivative 2 is also obtained from (2-diisopropylamino)ethanethiol 1b, or its disulfide 1c, with S2Cl2, in a rare conversion of a thiol or disulfide into the corresponding chloro compound. Compounds 2 and 5 are also obtained from N-(2-hydroxyethyl)diisopropylamine 1d, though in much lower yields. The reaction of N-(2-phenylthioethyl) (1e) or N-(2-phthalimidoethyl)diisopropylamines 1f,g affords bisdithiolothiazines 7, 8, 9, and 11 and the dithiolopyrrole 10, A coherent set of reaction pathways for the formation of these products is proposed. X-ray crystallography shows that the bisdithiolothiazine ring system of 2 is folded out of planarity about the thiazine N-S vector, with the N-chloroethyl group folded back over the thiazine ring with the chlorine atom lying above the thiazine sulfur atom; the dithiolothiazine ring system of 5 has the thiazine ring in a "sofa" conformation.

  DOI：

  10.1021/jo9902345

文献信息

• Tertiary amine–S2Cl2 chemistry: interception of reaction intermediates
  作者：Carlos F. Marcos、Tomás Torroba、Oleg A. Rakitin、Ljudmila I. Souvorova、Charles W. Rees、Andrew J. P. White、David J. Williams

  DOI：10.1039/a708396c

  日期：——

  The reaction of N-(2-chloroethyl)diisopropylamine 1a with S2Cl2 allows the selective one-pot preparation of the tricyclic 4-(2-chloroethyl)bisdithiolothiazines 8 and 9 or, by addition of phosphorus pentasulfide at a late stage of the reaction, of the dithiolothiazine 6b characterised by X-ray crystallography; the chloroethyl derivative 8 is also obtained from (2-diisopropylamino)ethanethiol 1b and its disulfide 1c and S2Cl2, in a rare conversion of a thiol or disulfide into the corresponding chloro compound.

  通过 N-(2-氯乙基)二异丙基胺 1a 与 S2Cl2 的反应，可以选择性地一次性制备出三环 4-(2-氯乙基)双硫代噻嗪 8 和 9，或者在反应后期加入五硫化二磷，制备出 X 射线晶体学表征的二硫代噻嗪 6b；从（2-二异丙基氨基）乙硫醇 1b 及其二硫化物 1c 和 S2Cl2 中也可以得到氯乙基衍生物 8，这是一种罕见的将硫醇或二硫化物转化为相应的氯化合物的方法。
• Synthesis of Highly Branched Sulfur−Nitrogen Heterocycles by Cascade Cycloadditions of [1,2]Dithiolo[1,4]thiazines and [1,2]Dithiolopyrroles
  作者：Susana Barriga、Pedro Fuertes、Carlos F. Marcos、Tomás Torroba

  DOI：10.1021/jo035748p

  日期：2004.5.1

  same dipolarophiles gave the 1:2, 1:3, or 1:4 adducts 5a−c, 6a, 7a, 8a, 9a, and 10a,c,d selectively in fair to high yields. Reaction conditions were crucial for achievement of selectivity in thermal reactions. Catalysis by scandium triflate was used in the reaction of 4a and 2 equiv of DMAD. Treatment of the [1,2]dithiolo[1,4]thiazine dithione 11 with DBA gave the 1:2, 1:3 (two isomers), and 1:4 adducts

  我们报告了通过级联环加成到容易获得的多环1,2-二硫代3-硫酮上的一些新的多硫-氮杂环的合成。因此，用乙炔二羧酸二甲酯（DMAD）或二苯甲酰基乙炔（DBA）处理双[1,2]二硫代吡咯并二硫酮1，得到1：4加合物2a，b和3a。另一方面，双[1,2]二硫代[1,4]噻嗪二硫酮4a - d与相同的双亲性化合物环加成后，可得到1：2、1：3或1：4加合物5a - c，6a，7a，8a，9a和10a，c，d有选择地以中等至高产。反应条件对于实现热反应的选择性至关重要。三氟甲磺酸scan的催化用于4a和2当量的DMAD的反应。的[1,2] dithiolo [1,4]噻嗪二硫酮治疗11具有DBA得到1：2,1：3（两种异构体），和1：4分的加合物12 - 14和15A - d选择性。所选实施例的循环伏安法显示出不可逆过程，不受与杂环系统键合的外围基团的影响。
• Synthesis of Bis[1,2]dithiolo[1,4]thiazines and a [1,2]Dithiolo[1,4]thiazine from Tertiary Diisopropylamines
  作者：Charles W. Rees、Andrew J. P. White、David J. Williams、Oleg A. Rakitin、Lidia S. Konstantinova、Carlos F. Marcos、Tomás Torroba

  DOI：10.1021/jo9902345

  日期：1999.7.1

  The reaction of N-(2-chloroethyl)diisopropylamine 1a with S2Cl2 allows the selective one-pot preparation of the tricyclic 4-(2-chloroethyl) bisdithiolothiazines 2-4 or, by addition of phosphorus pentasulfide at a rate stage in the reaction, of the dithiolothiazine 5. The chloroethyl derivative 2 is also obtained from (2-diisopropylamino)ethanethiol 1b, or its disulfide 1c, with S2Cl2, in a rare conversion of a thiol or disulfide into the corresponding chloro compound. Compounds 2 and 5 are also obtained from N-(2-hydroxyethyl)diisopropylamine 1d, though in much lower yields. The reaction of N-(2-phenylthioethyl) (1e) or N-(2-phthalimidoethyl)diisopropylamines 1f,g affords bisdithiolothiazines 7, 8, 9, and 11 and the dithiolopyrrole 10, A coherent set of reaction pathways for the formation of these products is proposed. X-ray crystallography shows that the bisdithiolothiazine ring system of 2 is folded out of planarity about the thiazine N-S vector, with the N-chloroethyl group folded back over the thiazine ring with the chlorine atom lying above the thiazine sulfur atom; the dithiolothiazine ring system of 5 has the thiazine ring in a "sofa" conformation.