(E,Z)-Bis(1-propenyl) disulfide | 121609-82-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: (E,Z)-Bis(1-propenyl) disulfide
• 英文别名: (E,Z)-di-1-propenyl disulfide；1-((E)-Prop-1-en-1-yl)-2-((Z)-prop-1-en-1-yl)disulfane；(Z)-1-[[(E)-prop-1-enyl]disulfanyl]prop-1-ene
• CAS: 121609-82-3
• 化学式: C₆H₁₀S₂
• 分子量: 146.277
• InChiKey: FHSDVOJKLYJNCQ-CIIODKQPSA-N

物化性质

• 沸点：
  186.1±13.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)
• 保留指数：
  1124

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,Z)-Bis(1-propenyl) disulfide 生成 3,4-二甲基噻吩
  参考文献：
  名称：

  Allium Chemistry:  Synthesis and Sigmatropic Rearrangements of Alk(en)yl 1-Propenyl Disulfide S-Oxides from Cut Onion and Garlic¹

  摘要：

  Reduction (LiAlH4) of propyl 1-propynyl sulfide (8) to (E)-1-propenyl propyl sulfide ((E)-10), C-S cleavage (Li/NH3) to lithium (E)-1-propenethiolate (Li(E)-11), and reaction with MeSO(2)Cl gives (E,E)-bis(1-propenyl) disulfide ((E,E)-2); i-Bu(2)AlH reduction of 8 to (Z)-10 and reaction with Li/NH3 and then MeSO(2)Cl gives (Z,Z)-2 via Li (Z)-11. Reaction of MeSO(2)SR (R = Me (12a), n-Pr (12b), CH2CH=CH2 (12c), CH=CHMe (12d)) with K (E)-11 gives (E,Z)-2 from (Z)-12d; Li (E,Z)-11 gives alkyl (E)- and (Z)-1-propenyl disulfides (MeCH=CHSSR, R = Me (3a), n-Pr (3b), CH2=CHCH2 (3c)) from 12a-c, respectively. Oxidation at -60 degrees C of (E,E)-, (Z,Z)-, and (E,Z)-2 gives (E)-1-propenesulfinothioic acid S-(E)-1-propenyl ester ((E,E)-13, (E,E)-MeCH=CHS(O)SCH=CHMe) from (E,E)-2, (Z,Z)-13 from (Z,Z)-2, and ca. 2:1 (E,Z)-13)/(Z,E)-13 from (E,Z)-2. Warming (Z,Z)-13 gives (+/-)-(1 alpha,2 alpha,3 beta,4 alpha,5 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (1a), endo-5-methyl-exo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2.1]heptane (14a), and exo-5-methyl-endo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2. 1]heptane (14b). Warming (E,E)-13 gives 14a and 14b; (E,Z)-13/(Z,E)-13 gives (1 alpha,2 alpha,3 alpha,4 alpha,5 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (1b), exo-5-methyl-exo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2.1]heptane (14c), and endo-5-methyl-endo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2.1]heptane (14d). Oxidation of 3a-c gives MeCH=CHSS(O)R (4) and MeCH=CHS(O)SR (5). At -60 degrees C, m-CPBA (2 equiv) converts (E,E)-2 into (Z,Z)-d,l-2,3-dimethyl-1,4-butanedithial 1,4-dioxide (26) while (Z,Z)-2 gives meso- and d,l-26. With NaIO4, 4/5 (R = Me) gives (E)- or (Z)-12a and MeCH=CHSO(2)SMe (6a); with m-CPBA (Z)-MeS(O)CHMeCH=S+-O- (25a) forms. At 85 degrees C 2 gives 1:1 cis- and trans-2-mercapto-3,4-dimethyl-2,3-dihydrothiophene (29).

  DOI：

  10.1021/ja953444h
• 作为产物：
  描述：

  Potassium (E)-1-propenethiolate 、 (Z)-S-1-propenyl methanesulfonothioate 以60%的产率得到(E,Z)-Bis(1-propenyl) disulfide
  参考文献：
  名称：

  Allium chemistry: simple synthesis of antithrombotic cepaenes from onion and deoxycepaenes from oil of shallot by reaction 1-propenethiolate with sulfonyl halides

  摘要：

  Stereoisomers of MeCH=CHSLi from Li/NH3 reduction of MeCH=CHSPr react with varying proportions of MsCl giving the respective stereoisomers of either bis(1-propenyl) disulfide (1), S-1-propenyl methane-sulfonothiate (2a), or 6-ethyl-4,5,7-trithiadeca-2,8-diene (3); oxidation of 3, a shallot oil component, gives 6-ethyl-4,5,7-trithiadeca-2,8-diene 7-oxide (cepaene, 4), an antithrombotic compound from onion.

  DOI：

  10.1021/jo00048a007

文献信息

• Apparatus, method and composition for repelling animals
  申请人：——

  公开号：US20030091664A1

  公开（公告）日：2003-05-15

  An apparatus, method and composition for repelling animals are disclosed. The apparatus comprises a layer extracted from a plant of an Alliaceae family on a substrate, wherein the substrate is selected from the group consisting of plants, living animals and manufactured objects and combinations thereof. The method comprises extracting a plant of an Alliaceae family, Allium genus; and applying the extract to an exposed surface of a substrate, wherein the substrate is selected from the group consisting of plants, living animals, manufactured objects and combinations thereof. The composition comprises an extract of a plant of an Alliaceae family, Allium genus; and at least one egg, having a yolk portion.

  本发明公开了一种驱赶动物的装置、方法和组合物。该装置包括在基质上的一层从万年青科植物中提取的提取物，其中基质选自由植物、活体动物和人造物体及其组合组成的组。该方法包括提取茜草科、薤属植物；并将提取物涂抹在基质的暴露表面，其中基质选自由植物、活体动物、人造物品及其组合组成的组。该组合物包括茜草科、薤属植物的提取物；以及至少一个具有蛋黄部分的鸡蛋。
• Onion essential oil chemistry. Cis-and trans-2-mercapto-3,4-dimethyl 2,3-dihydrothiophene from pyrolysis of bis(1-propenyl) disulfide
  作者：Eric Block、Hai Zhao Shu

  DOI：10.1016/s0040-4039(00)97788-8

  日期：1990.1
• Characterization of typical potent odorants in raw and cooked Toona sinensis (A. Juss.) M. Roem. by instrumental-sensory analysis techniques
  作者：Wenxi Yang、Keith R. Cadwallader、Yuping Liu、Mingquan Huang、Baoguo Sun

  DOI：10.1016/j.foodchem.2018.12.112

  日期：2019.6

  Toona sinensis (A. Juss.) M. Roem. (TS) possesses a unique and pleasant flavor and is consumed as a popular seasonal vegetable in certain parts of eastern and southeastern Asia. The potent odorants in raw and cooked TS were identified by combined sensory and instrumental analysis techniques, including sensory descriptive aroma profiling and two complimentary volatile isolation methods combined with gas chromatography-olfactometry (GC-O) techniques. Highly volatile odorants were determined by static headspace dilution analysis (SHDA)-GCO, while those of intermediate-and semi-volatility were determined by solvent-assisted flavor evaporationaroma extract dilution analysis (SAFE-AEDA). Among the numerous odorants identified by SHDA and SAFEAEDA, (E, E)-bis-(1-propenyl) disulfide was found to be predominant in both raw and cooked TS. In agreement with results of sensory descriptive analysis, hexanal, (Z)-3-hexenal, (E)-2-hexenal and (Z)-3-hexen-1-ol contributed green, grassy and leafy aroma notes; while hydrogen sulfide, methyl thiirane, (E, E)-bis-(1-propenyl) disulfide and (E, Z)-bis-(1-propenyl) disulfide contributed pungent, sulfurous and alliaceous notes in TS.
• <i>Allium</i> Chemistry:  Synthesis and Sigmatropic Rearrangements of Alk(en)yl 1-Propenyl Disulfide <i>S</i>-Oxides from Cut Onion and Garlic¹
  作者：Eric Block、Thomas Bayer、Sriram Naganathan、Shu-Hai Zhao

  DOI：10.1021/ja953444h

  日期：1996.1.1

  Reduction (LiAlH4) of propyl 1-propynyl sulfide (8) to (E)-1-propenyl propyl sulfide ((E)-10), C-S cleavage (Li/NH3) to lithium (E)-1-propenethiolate (Li(E)-11), and reaction with MeSO(2)Cl gives (E,E)-bis(1-propenyl) disulfide ((E,E)-2); i-Bu(2)AlH reduction of 8 to (Z)-10 and reaction with Li/NH3 and then MeSO(2)Cl gives (Z,Z)-2 via Li (Z)-11. Reaction of MeSO(2)SR (R = Me (12a), n-Pr (12b), CH2CH=CH2 (12c), CH=CHMe (12d)) with K (E)-11 gives (E,Z)-2 from (Z)-12d; Li (E,Z)-11 gives alkyl (E)- and (Z)-1-propenyl disulfides (MeCH=CHSSR, R = Me (3a), n-Pr (3b), CH2=CHCH2 (3c)) from 12a-c, respectively. Oxidation at -60 degrees C of (E,E)-, (Z,Z)-, and (E,Z)-2 gives (E)-1-propenesulfinothioic acid S-(E)-1-propenyl ester ((E,E)-13, (E,E)-MeCH=CHS(O)SCH=CHMe) from (E,E)-2, (Z,Z)-13 from (Z,Z)-2, and ca. 2:1 (E,Z)-13)/(Z,E)-13 from (E,Z)-2. Warming (Z,Z)-13 gives (+/-)-(1 alpha,2 alpha,3 beta,4 alpha,5 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (1a), endo-5-methyl-exo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2.1]heptane (14a), and exo-5-methyl-endo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2. 1]heptane (14b). Warming (E,E)-13 gives 14a and 14b; (E,Z)-13/(Z,E)-13 gives (1 alpha,2 alpha,3 alpha,4 alpha,5 beta)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (1b), exo-5-methyl-exo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2.1]heptane (14c), and endo-5-methyl-endo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2.1]heptane (14d). Oxidation of 3a-c gives MeCH=CHSS(O)R (4) and MeCH=CHS(O)SR (5). At -60 degrees C, m-CPBA (2 equiv) converts (E,E)-2 into (Z,Z)-d,l-2,3-dimethyl-1,4-butanedithial 1,4-dioxide (26) while (Z,Z)-2 gives meso- and d,l-26. With NaIO4, 4/5 (R = Me) gives (E)- or (Z)-12a and MeCH=CHSO(2)SMe (6a); with m-CPBA (Z)-MeS(O)CHMeCH=S+-O- (25a) forms. At 85 degrees C 2 gives 1:1 cis- and trans-2-mercapto-3,4-dimethyl-2,3-dihydrothiophene (29).
• Allium chemistry: simple synthesis of antithrombotic cepaenes from onion and deoxycepaenes from oil of shallot by reaction 1-propenethiolate with sulfonyl halides
  作者：Eric Block、Shu Hai Zhao

  DOI：10.1021/jo00048a007

  日期：1992.10

  Stereoisomers of MeCH=CHSLi from Li/NH3 reduction of MeCH=CHSPr react with varying proportions of MsCl giving the respective stereoisomers of either bis(1-propenyl) disulfide (1), S-1-propenyl methane-sulfonothiate (2a), or 6-ethyl-4,5,7-trithiadeca-2,8-diene (3); oxidation of 3, a shallot oil component, gives 6-ethyl-4,5,7-trithiadeca-2,8-diene 7-oxide (cepaene, 4), an antithrombotic compound from onion.