1,2,3,4-tetrathia-6,7-dimethyl-6-cyclooctene | 139174-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,2,3,4-tetrathia-6,7-dimethyl-6-cyclooctene
• 英文别名: (6Z)-6,7-dimethyl-5,8-dihydrotetrathiocine
• CAS: 139174-04-2
• 化学式: C₆H₁₀S₄
• 分子量: 210.409
• InChiKey: PLKAFOWVSLJYMD-WAYWQWQTSA-N

物化性质

• 沸点：
  324.5±45.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrathia-6,7-dimethyl-6-cyclooctene 在 三苯基膦 作用下， 生成 1,2-二硫杂-4,5-二甲基-4-环己烯
  参考文献：
  名称：

  氯（三苯甲基）二硫化物与1,3-二烯的反应：环状二硫化物和四硫化物的合成。

  摘要：

  氯（三苯基甲基）二硫化物（3）与2,3-二甲基-1,3-丁二烯（4）反应生成环状二硫化物5（与捕获双原子硫一致的产物）以及环状四硫化物6。

  DOI：

  10.1016/0040-4039(91)80556-l
• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 在 triphenylmethanethiosulfenyl chloride cyclohexen 作用下， 以 乙酸乙酯 为溶剂， 反应 10.0h， 以54%的产率得到1,2,3,4-tetrathia-6,7-dimethyl-6-cyclooctene
  参考文献：
  名称：

  磺酰氯化学。双原子硫转移的前体

  摘要：

  三苯基甲硫基亚硫酰氯1 [（C 6 H 5）3 CSSCl]（及其二硫代同系物2 [（C 6 H 5）3 CSSSCl]）与环戊烯和环己烯形成稳定的加成产物（产率约85％）。当这些加合物被二烯加热时，它们会释放出双原子的硫捕获的衍生物。用三苯基膦将这些四硫化物定量转化为相应的二硫化物3。这提供了环状二硫化物，从二烯分离出的产率为50％。此外，已经获得了涉及二硫杂环戊烷中间体4的证据。

  DOI：

  10.1016/0040-4039(94)85351-7

文献信息

• An S-oxide of 6-tert-butyl-6-phenylpentathiane. Structure in the crystalline state and in solution and thermal decomposition
  作者：Akihiko Ishii、Hideaki Oshida、Juzo Nakayama

  DOI：10.1016/s0040-4039(01)00383-5

  日期：2001.4

  Oxidation of 6-tert-butyl-6-phenylpentathiane with trifluoroperacetic acid gave the pentathiane 3-oxide mainly as the monooxide. The 3-oxide takes a twist conformation both in the crystalline state and in solution. Thermal decomposition of the 3-oxide in the presence of 2,3-dimethyl-1,3-butadiene yielded both S2O- and S2-transferred products.

  用三氟过氧乙酸氧化6-叔丁基-6-苯基戊烷得到的戊烷3-氧化物主要为一氧化物。3-氧化物在晶体状态和溶液中均具有扭曲构象。在2，3-二甲基-1，3-丁二烯存在下3-氧化物的热分解产生了S 2 O-和S 2转移的产物。
• Sulfur allotrope chemistry—S10 an effective two-sulfur transfer reagent
  作者：Pierre Lesté-Lasserre、David N. Harpp

  DOI：10.1016/s0040-4039(99)01657-3

  日期：1999.11

  The chemistry of one of the sulfur allotropes has been investigated. Cyclodecasulfur (S10) reacts with conjugated 1,3-dienes and strained olefins to deliver cyclic di- and polysulfides with a better selectivity and under milder conditions than with elemental sulfur (S8). A radical mechanism is proposed for these sulfuration reactions.

  已经研究了一种硫同素异形体的化学性质。环十二碳硫素（S 10）与共轭1,3-二烯和张力烯烃反应，以比元素硫（S 8）更好的选择性和更温和的条件提供环状二硫化物和多硫化物。提出了用于这些硫化反应的自由基机理。
• Diatomic sulfur transfer from stable alkoxy disulfides
  作者：Sylvie L. Tardif、Charles R. Williams、David N. Harpp

  DOI：10.1021/ja00140a024

  日期：1995.9
• Structure and chemistry of chloro(triphenylmethyl)sulfanes
  作者：Charles R. Williams、James F. Britten、David N. Harpp

  DOI：10.1021/jo00083a022

  日期：1994.2

  The structures of chloro(triphenylmethyl)mono-, di-, and -trisulfanes were obtained. The monosulfane displayed a triclinic (P1) space group, a = 10.792(2) Angstrom, b = 15.090(2) Angstrom, c = 10.027(2) Angstrom, alpha = 100.15(1)degrees, beta 103.13(1)degrees, gamma = 88.80(1)degrees, Z = 4. The disulfane gave a triclinic (P1) space group, a = 9.758(1) Angstrom, b = 10.426(2) Angstrom, c = 9.1691(6) Angstrom, alpha = 97.52(1)degrees, beta = 90.116(1)degrees, gamma = 116.750(1)degrees, Z = 2. The trisulfane gave an orthorhombic space group (Pna2(1)), a = 9.224(1) Angstrom, b = 19.196(3) Angstrom, c = 10.308(1) Angstrom, Z = 4. The sulfenyl chlorides decompose above their melting points to mixtures consisting primarily of triphenylchloromethane and sulfur. The sulfur was determined to consist of several allotropes (S-6, S-7, S-8, and S-9). The di- and trisulfanes slowly decompose to the same products at room temperature; the decompositions are enhanced by light. The decomposition of the trisulfane in the presence of dienes gave adducts consistent with the transfer of a two-sulfur species. The disulfane and trisulfane undergo the normal nucleophilic substitution reactions of the monosulfanes.
• Sulfenyl Chloride Chemistry. New Precursors for Diatomic Sulfur Transfer
  作者：Imad A. Abu-Yousef、David N. Harpp

  DOI：10.1021/jo9710792

  日期：1998.11.1

  When triphenylmethanesulfenyl chloride (1) (or its thio homologue 2) are treated with various bicycles, norbornene (5), or bicyclo[2.2.2]octene (6), dithio adducts 7 and 8 were produced in good isolated yields. Final products were obtained via an episulfide intermediate. The stereochemistry of addition has been determined by X-ray analysis. Treatment of thiosulfenyl chloride 2 (or its dithio homologue 3) with other olefins, cyclopentene (10), cyclohexene (11), or 1,4-dioxene (12), leads to the formation of disulfides (13-15 from 2) and trisulfides (16 and 17 from 3) in high isolated yields (ca. 92%). The structures of 7, 8, and 13-17 were established by H-1 and C-13 NMR and elemental analysis as well as by X-ray determination. When these adducts are warmed with a 1,3-diene 42, they deliver diatomic sulfur-trapped derivatives, cyclic di-49 and tetrasulfide adducts 46. A variety of solvents, temperatures, times, and concentrations were employed to optimize the yield of 46 and 49. The tetrasulfide adduct 46 is quantitatively converted to disulfide 49 with triphenylphosphine; this affords cyclic disulfides in >50% isolated yield from the diene. In addition, evidence has been obtained implicating dithietane intermediate 4.