6,7-dihydro-2,3-dimethyl 5H-2a-thia(2a-S^IV)-2,3,4a,7a-tetraazacyclopentindene-1,4(2H,3H)-dithione | 72885-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6,7-dihydro-2,3-dimethyl 5H-2a-thia(2a-S^IV)-2,3,4a,7a-tetraazacyclopentindene-1,4(2H,3H)-dithione
• 英文别名: 2,3-dimethyl-6,7-dihydro-5H-2a-thia(2a-S(IV))-2,3,4a,7a-tetraazacyclopentindene-1,4(2H,3H)-dithione；3,4-dimethyl-1,6-propano-1H,6H-3a-thia(S^IV)-1,3,4,6-tetraazapentalene-2,5(3H,4H)-dithione；3,5-Dimethyl-4lambda4-thia-1,3,5,7-tetrazatricyclo[5.3.1.04,11]undec-4(11)-ene-2,6-dithione；3,5-dimethyl-4λ4-thia-1,3,5,7-tetrazatricyclo[5.3.1.04,11]undec-4(11)-ene-2,6-dithione
• CAS: 72885-84-8
• 化学式: C₈H₁₂N₄S₃
• 分子量: 260.408
• InChiKey: XSLHKDJSOOGDRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dihydro-2,3-dimethyl 5H-2a-thia(2a-S^IV)-2,3,4a,7a-tetraazacyclopentindene-1,4(2H,3H)-dithione 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 以70%的产率得到1,3-bis(methyl thiocarbamoyl)perhydropyrimidine
  参考文献：
  名称：

  Reduction of 3,4-Disubstituted 1,6-Propano-1H,6H-3a-thia(SIV)-1,3,4,6-tetraazapentalene-2,5(3H,4H)-dithione with Sodium Borohydride

  摘要：

  DOI：

  10.3987/r-1987-12-3097
• 作为产物：
  描述：

  3,4,5,6-四氢-2-嘧啶硫醇 、 异硫氰酸甲酯 在 正丁基锂 、 alpha-氯乙酰苯 作用下， 以 四氢呋喃 为溶剂， 生成 6,7-dihydro-2,3-dimethyl 5H-2a-thia(2a-S^IV)-2,3,4a,7a-tetraazacyclopentindene-1,4(2H,3H)-dithione
  参考文献：
  名称：

  Hayashi, Hirokazu; Matsumura, Noboru; Mizuno, Kazuhiko, Journal of Chemical Research, 2004, # 9, p. 599 - 601

  摘要：

  DOI：

文献信息

• Reaction of tetraazathiapentalene and thiadiazolopyrimidine derivatives with heterocumulenes: Cycloaddition and elimination reactions<i>via</i>hypervalent sulfur intermediates
  作者：Noboru Matsumura、Atsushi Ito、Masaaki Tomura、Yasuyuki Okumura、Kazuhiko Mizuno

  DOI：10.1002/jhet.5570410116

  日期：2004.1

  Tetraazathiapentalene derivative 1 reacts with heterocumulenes such as diphenylketene (2) and 2-pyridylisothiocyanate (5) to give heterocycles 3, 6 and 7 with elimination of methylisothiocyanate. The reactions of thiadiazolopyrimidine derivatives 8a-b with ethoxycarbonyl isothiocyanate (9) and carbon disulfide (11) gives heterocycles 10 and 12 via thermal decomposition of 1:1 cycloadducts C and D which

  四氮杂戊戊烯衍生物1与杂枯烯如二苯乙烯酮（2）和2-吡啶基异硫氰酸酯（5）反应，得到杂环3、6和7，同时消除了异硫氰酸甲酯。噻二唑并嘧啶衍生物8a-b与乙氧基羰基异硫氰酸酯（9）和二硫化碳（11）的反应通过1∶1的具有高价硫的环加合物C和D的热分解产生杂环10和12 。描述了这些反应的机理和反应性特征。
• Synthesis of Novel Tetraazapentalene Derivatives (10-S-3) with a Hypervalent Sulfur and Carbonyl Groups
  作者：Noboru Matsumura、Osamu Mori、Masaaki Tomura、Shigeo Yoneda

  DOI：10.1246/cl.1989.39

  日期：1989.1

  Tetraazapentalenes (R = CH3 and CH2=CHCH2) reacted with isocyanates to give new types of tetraazapentalenes, (2) and (3). The compounds, 2 and 3 were also obtained by the reaction of isocyanates with thiadiazolopyrimidines.

  四氮杂戊搭烯（R = CH3 和 CH2=CHCH2）与异氰酸酯反应，生成新型四氮杂戊搭烯（2）和（3）。化合物2和3还可以通过异氰酸酯与噻二唑并嘧啶的反应获得。
• Reactions of Alkyl Isothiocyanates with Dianions of Cyclic Thioureas
  作者：Noboru Matsumura、Masaaki Tomura、Ritsuo Mando、Yuko Tsuchiya、Shigeo Yoneda

  DOI：10.1246/bcsj.59.3693

  日期：1986.11

  The reactions of methyl (or ethyl) isothiocyanate with dianions (4, 5, and 6), which are readily derived from available cyclic thioureas (1, 2, and 3) with butyllithium, gave ring fused 1,3-disubstituted 1,3,5-triazine-2,4(1H,3H)-dithiones (7) and/or thiocarbamoyl derivative (8) as major products.

  异硫氰酸甲酯（或乙基）与二价阴离子（4、5 和 6）（容易从可用的环状硫脲（1、2 和 3）与丁基锂衍生）反应，得到稠环 1,3-二取代的 1,3 ,5-三嗪-2,4(1H,3H)-二硫酮 (7) 和/或硫代氨基甲酰基衍生物 (8) 作为主要产物。
• Photoinduced Electron Transfer Reaction of Tetraazathiapentalenes with Trialkylamines
  作者：Hirokazu Hayashi、Noboru Matsumura、Kazuhiko Mizuno

  DOI：10.1246/cl.2002.510

  日期：2002.5

  The photoinduced electron transfer reaction of tetraazathiapentalenes with trialkylamines gives thiourea derivatives by dialkylamination of isothiocyanate derivatives, through radical anions of tetraazathiapentalenes and radical cations of trialkylamines.

  四氮杂五环烯与三烷基胺的光诱导电子转移反应通过四氮杂五环烯的自由基阴离子和三烷基胺的自由基阳离子，产生异硫氰酸酯衍生物的二烷基氨基化，从而生成硫脲衍生物。
• Synthesis and Structure of 6,7-Dihydro-2,3-disubstituted 5<i>H</i>-2a-Thia(2<i>a</i>-<i>S</i>^IV)-2,3,4a,7a-tetraazacyclopent[<i>cd</i>]indene-1,4(2<i>H</i>,3<i>H</i>)-dithione
  作者：Noboru Matsumura、Masaaki Tomura、Osamu Mori、Yuko Tsuchiya、Shigeo Yoneda、Koshiro Toriumi

  DOI：10.1246/bcsj.61.2419

  日期：1988.7

  Symmetrical tetraazapentalene derivatives 5 and 6 were synthesized by a convenient one-pot reaction using lithium thioureide/phenacyl chloride/alkyl (or allyl) isothiocyanate system. Unsymmetrical tetraazapentalene derivatives 8 were prepared by the reaction of various isothiocyanates with thiadiazolopyrimidine derivatives 7 which were derived from symmetrical tetraazapentalene derivatives. The structure of 5c was determined by a single crystal X-ray diffraction.

  采用硫脲锂/苯甲酰氯/烷基（或烯丙基）异硫氰酸酯体系，通过便捷的一锅反应合成了对称的四氮杂戊二烯衍生物5和6。不对称四氮杂五环戊二烯衍生物8是通过各种异硫氰酸酯与衍生自对称四氮杂五环戊二烯衍生物的噻二唑并嘧啶衍生物7反应制备的。通过单晶X射线衍射确定了5c的结构。