Bis(prop-2-enyl)-sulfanylidene-lambda4-sulfane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 烯丙基硫化合物
• 英文名称: Bis(prop-2-enyl)-sulfanylidene-lambda4-sulfane
• 英文别名: bis(prop-2-enyl)-sulfanylidene-λ4-sulfane
• 化学式: C₆H₁₀S₂
• 分子量: 146.277
• InChiKey: WGJRJJBYRQHJQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二烯丙基二硫 以 phosphate buffer 为溶剂， 反应 0.5h， 生成 Bis(prop-2-enyl)-sulfanylidene-lambda4-sulfane
  参考文献：
  名称：

  Selective effects of diallyl disulfide, a sulfane sulfur precursor, in the liver and Ehrlich ascites tumor cells

  摘要：

  The present in vivo studies demonstrated that diallyl disulfide (DADS), occurring in garlic, elevated hepatic sulfane sulfur level and activities of gamma-cystathionase and 3-mercaptopyruvate sulfotransferase in healthy mice but did not affect the hepatic glutathione level. DADS efficiently corrected the concentrations of glutathione and sulfane sulfur, and ameliorated gamma-cystathionase activity that had been lowered in the livers of Ehrlich ascites tumor-bearing mice. In Ehrlich ascites tumor cells, diallyl disulfide did not alter bound sulfane sulfur level, sulfotransferases activity or glutathione level. These data indicate that this compound is capable of acting efficiently and selectively only in the liver and can be used for hepatoprotection during chemotherapy. (c) 2007 Elsevier B.V All rights reserved.

  DOI：

  10.1016/j.ejphar.2007.04.055

文献信息

• DECHALCOGENATIVE METHODS FOR THE PREPARATION OF ALLYLIC SULFIDES
  申请人：Crich David

  公开号：US20100222549A1

  公开（公告）日：2010-09-02

  A dechalcogenative method for the preparation of an allylic sulfide comprises contacting an activated chalcogenide of Formula (I) with a thiol of Formula (II) for a period of time sufficient to form an intermediate of Formula (III), and supplying sufficient activation energy to the intermediate of Formula (III), in a suitable solvent, preferably in the absence of a phosphine or other thiophile, to induce a [2,3]-sigmatropic rearrangement therein to form an allylic sulfide of Formula (IV), with concomitant loss of chalcogen Z, as set forth in the following reaction scheme, wherein X is an activating group selected from the group consisting of CN, S-pyridyl, S-heteroaryl, SO2-aryl, and SO3Y; Y is an alkali metal ion; Z is Se or S; R1, R2, R3, R4, and R5 are each independently H or a hydrocarbon moiety; and R is an organic moiety.

  一种去硫代化的方法，用于制备烯丙基硫醚，包括将式(I)激活的硫族元素与式(II)的硫醇接触一段足够的时间，以形成式(III)的中间体，并向该中间体提供足够的激活能量，在适当的溶剂中，优选地在缺少膦或其他硫亲和性试剂的情况下，诱导[2,3]-sigmatropic重排反应，以形成式(IV)的烯丙基硫醚，同时失去硫族元素Z，如下反应方程所示，其中X是从CN、S-吡啶基、S-杂环基、SO2-芳基和SO3Y等组中选择的活化基团；Y是碱金属离子；Z是Se或S；R1、R2、R3、R4和R5各自独立地是氢或碳氢基团；R是有机基团。
• [EN] DECHALCOGENATIVE METHODS FOR THE PREPARATION OF ALLYLIC SULFIDES<br/>[FR] PROCÉDÉS DÉCHALCOGÉNATIFS POUR LA PRÉPARATION DE SULFURES ALLYLIQUES
  申请人：UNIV ILLINOIS

  公开号：WO2008134058A1

  公开（公告）日：2008-11-06

  [EN] A dechalcogenative method for the preparation of an allylic sulfide comprises contacting an activated chalcogenide of Formula (I) with a thiol of Formula (II) for a period of time sufficient to form an intermediate of Formula (III), and supplying sufficient activation energy to the intermediate of Formula (III), in a suitable solvent, preferably in the absence of a phosphine or other thiophile, to induce a [2,3]-sigmatropic rearrangement therein to form an allylic sulfide of Formula (IV), with concomitant loss of chalcogen Z, as set forth in the following reaction scheme, wherein X is an activating group selected from the group consisting of CN, S-pyridyl, S-heteroaryl, SO2-aryl, and SO3Y; Y is an alkali metal ion; Z is Se or S; R1, R2, R3, R4, and R5 are each independently H or a hydrocarbon moiety; and R is an organic moiety.
  [FR] L'invention concerne un procédé déchalcogénatif pour la préparation d'un sulfure allylique qui comporte la mise en contact d'un chalcogénure activé de formule (I) avec un thiol de formule (II) pendant une période suffisante pour former un intermédiaire de formule (III) et la fourniture d'une énergie d'activation suffisante à l'intermédiaire de formule (III), dans un solvant approprié, de préférence en l'absence de phosphine ou d'autres thiophiles, pour induire un réagencement [2,3]-sigmatropique afin de former un sulfure allylique de formule (IV), avec une perte concomitante de chalcogène Z, comme exposé dans le schéma de réaction suivant, où X est un groupe activateur choisi dans le groupe constitué de CN, S-pyridyle, S-hétéroaryle, SO₂-aryle et SO₃Y ; Y est un ion de métal alcalin ; Z est Se ou S ; R¹, R², R³, R⁴ et R⁵ sont chacun indépendamment H ou une fraction hydrocarbure ; et R est une fraction organique.
• Selective effects of diallyl disulfide, a sulfane sulfur precursor, in the liver and Ehrlich ascites tumor cells
  作者：Małgorzata Iciek、Joanna Marcinek、Urszula Mleczko、Lidia Włodek

  DOI：10.1016/j.ejphar.2007.04.055

  日期：2007.8

  The present in vivo studies demonstrated that diallyl disulfide (DADS), occurring in garlic, elevated hepatic sulfane sulfur level and activities of gamma-cystathionase and 3-mercaptopyruvate sulfotransferase in healthy mice but did not affect the hepatic glutathione level. DADS efficiently corrected the concentrations of glutathione and sulfane sulfur, and ameliorated gamma-cystathionase activity that had been lowered in the livers of Ehrlich ascites tumor-bearing mice. In Ehrlich ascites tumor cells, diallyl disulfide did not alter bound sulfane sulfur level, sulfotransferases activity or glutathione level. These data indicate that this compound is capable of acting efficiently and selectively only in the liver and can be used for hepatoprotection during chemotherapy. (c) 2007 Elsevier B.V All rights reserved.