(E,E)-di-1-propenyl disulfide | 23838-23-5

• 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,E)-di-1-propenyl disulfide
• 英文别名: Disulfide, di-1-propenyl；(E)-1-[[(E)-prop-1-enyl]disulfanyl]prop-1-ene
• CAS: 23838-23-5
• 化学式: C₆H₁₀S₂
• 分子量: 146.277
• InChiKey: FHSDVOJKLYJNCQ-GGWOSOGESA-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：
  1129.1;1102

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,E)-di-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：

  n-propyl trans-1-propenyl sulfide 在 氨 、 lithium 、 甲基磺酰氯 作用下， 生成 (E,E)-di-1-propenyl disulfide
  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

文献信息

• Lubricating oil composition
  申请人：NIPPON OIL CO. LTD.

  公开号：EP0781834A2

  公开（公告）日：1997-07-02

  A lubricating oil composition comprises (A) a base oil, (B) a 3-methyl-5-tert-butyl-4-hydroxyphenyl substituted fatty acid ester in an amount of 0.1 - 5 percent by mass and (C) an auxiliary component, said auxiliary component being one member of the group of (a) a nitrogen-containing compound in an amount of 0.001 - 1 percent by mass, (b) a sulfur and/or phosphorus-containing compound in an amount of 0.1 - 5.0 percent by mass or (c) a phenolic compound in an amount of 0.1 - 5.0 percent by mass. This composition features the combination with a base oil of these specified components whereby there is provided synergistic effect conducive to inhibition or prevention of both oxidation and sludge formation while in use under elevated temperature conditions over extended periods of time.

  一种润滑油组合物包括：(A)基础油；(B)3-甲基-5-叔丁基-4-羟基苯基取代脂肪酸酯，其质量百分比为 0.1 - 5%；(C)辅助组分，所述辅助组分为以下组中的一种：(a)含氮化合物，其质量百分比为 0.001 - 1%；(b)含硫和/或磷化合物，其质量百分比为 0.1 - 5.0%；或(c)酚类化合物，其质量百分比为 0.001 - 1%（质量百分比），(b) 含硫和/或磷化合物，含量为 0.1 - 5.0%（质量百分比），或 (c) 酚类化合物，含量为 0.1 - 5.0%（质量百分比）。这种组合物的特点是将这些特定成分与基础油结合在一起，从而产生协同效应，有利于在高温条件下长时间使用时抑制或防止氧化和油泥的形成。
• 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。
• <i>Allium</i> Chemistry:  Synthesis of 1-[Alk(en)ylsulfinyl]propyl Alk(en)yl Disulfides (Cepaenes), Antithrombotic Flavorants from Homogenates of Onion (<i>Allium cepa</i>)
  作者：Eric Block、Harsh Gulati、David Putman、Deyou Sha、Niannian You、Shu-Hai Zhao

  DOI：10.1021/jf9705126

  日期：1997.11.1

  A series of 1-[alk(en)ylsulfinyl]propyl alk(en)yl disulfides (alpha-sulfinyl disulfides) of structure RS(O)CHEtSSR', R, R' = Me, (E,Z)-MeCH=CH, n-Pr, and CH2=CHCH2, termed cepaenes, have been synthesized by a variety of routes including oxidation of 1-[alk(en)ylthio]propyl alk(en)yl disulfides, RSCHEtSSR', termed deoxycepaenes. The cepaenes are identical to compounds isolated from homogenates of onion (Allium cepa) and to compounds identified in these homogenates by liquid chromatography/mass spectrometry, while the deoxycepaenes are identical to compounds found in Allium distilled oils and in other materials: The antithrombotic activities for several cepaenes are reported.
• 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.