cis-Propenyl-propyl-disulfid | 23838-20-2

• 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: cis-Propenyl-propyl-disulfid
• 英文别名: 1-Propenyl propyl disulfide；1-[[(Z)-prop-1-enyl]disulfanyl]propane
• CAS: 23838-20-2
• 化学式: C₆H₁₂S₂
• 分子量: 148.293
• InChiKey: AAPBYIVJOWCMGH-HYXAFXHYSA-N

物化性质

• 沸点：
  185.9±13.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)
• LogP：
  3.182 (est)
• 物理描述：
  colourless liquid with odour of cooked onions
• 折光率：
  1.522-1.532
• 保留指数：
  1076;1077;1083.9;1094

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  cis-Propenyl-propyl-disulfid 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-propanesulfinothioic acid S-(Z)-1-propenyl ester 、 (Z)-1-propenesulfinothioic acid S-n-propyl ester
  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：

  S-丙基甲烷硫代磺酸酯 、 1c-propylsulfanyl-propene 在 氨 、 lithium 作用下， 生成 cis-Propenyl-propyl-disulfid
  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

• 1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents
  申请人：IMAX Discovery GmbH

  公开号：EP2832233A1

  公开（公告）日：2015-02-04

  The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

  本发明主要涉及式(I)的1H-吡咯-2,4-二羰基衍生物，其中R1、R2、R3、Z、Z'和J按描述定义，及其混合物，以及用作调味剂的使用。根据本发明的化合物适用于生产、赋予或增强鲜味。本发明进一步涉及包含式(I)化合物或式(I)化合物混合物的有效量的调味混合物、口腔消费的组成物以及即食、即用和半成品，以及用于生产、赋予、改变和/或增强特定风味印象的特定方法。
• Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents
  申请人：IMAX Discovery GmbH

  公开号：EP2832234A1

  公开（公告）日：2015-02-04

  The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

  本发明主要涉及式(I)的咪唑[1,2-a]吡啶基甲基衍生物，其中R1、R2、X、W和J如描述中定义，以及涉及它们的混合物和使用它们作为调味剂。根据本发明的化合物适合于产生、赋予或增强鲜味。本发明进一步涉及调味混合物、口腔摄入的配方以及包含有效量的式(I)化合物的即食、即用和半成品，以及用于生产、赋予、改变和/或增强特定风味印象的特定方法。
• 1-tert-Butylcyclohexanecarboxamide and uses thereof as cooling compounds
  申请人：Kazimierski Arkadiusz

  公开号：US20110070329A1

  公开（公告）日：2011-03-24

  Described is a new cooling agent represented by Formula I and compositions with known coolers having cooling properties and the application of Formula I in foodstuffs and chewing gum: wherein X, Y is independently selected from a C1-C4 straight or branched alkyl or H atom; and m is 0, 1 or 2, Z when present is nitrogen, W and W′ are selected independently from the group consisting of H, OH, C1-C4 straight or branched alkyl, and a C1-C4 straight or branched alkoxy or W is group (CH 2 )n-R, where n is 0 or 1 and R is a group with non-bonding electrons. Useful groups with non-bonding electrons are halogens, OH, OMe, OEt, NO 2 , CN, Ac, SO 2 NH 2 , CHO, CO 2 H, CONH 2 , CONHR 2 , where R 2 is selected from C1-C4, and C1-C4 alkyl carboxylates such as CO 2 Me or CO 2 Et.

  描述了一种由化学式I代表的新冷却剂，以及具有冷却性能的已知冷却剂的组合物，以及化学式I在食品和口香糖中的应用：其中X、Y分别选自C1-C4直链或支链烷基或氢原子；m为0、1或2，Z存在时为氮，W和W′分别选自H、OH、C1-C4直链或支链烷基，以及C1-C4直链或支链烷氧基，或者W为基团(CH2)n-R，其中n为0或1，R是具有非成键电子的基团。具有非成键电子的有用基团包括卤素、OH、OMe、OEt、NO2、CN、Ac、SO2NH2、CHO、CO2H、CONH2、CONHR2，其中R2选自C1-C4烷基，以及C1-C4烷基羧酸酯，如CO2Me或CO2Et。
• Menthylcarboxamides and their use as cooling agents
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP2246323A1

  公开（公告）日：2010-11-03

  Described is a new cooling agent represented by Structure I and compositions with known coolers having cooling properties and the application of Structure I in foodstuffs and chewing gum:

  描述了一种由结构I表示的新的冷却剂，以及具有冷却性能的已知冷却剂的组合物，以及在食品和口香糖中应用结构I的方法。
• Menthylcarboxamides and Their Use as Cooling Agents
  申请人：Bardsley Kathryn Anne

  公开号：US20100272655A1

  公开（公告）日：2010-10-28

  Described is a new cooling agent represented by Structure I and compositions with known coolers having cooling properties and the application of Structure I in foodstuffs and chewing gum:

  本文描述了一种由结构I代表的新型冷却剂及其与已知冷却剂具有冷却性能的组合物，以及结构I在食品和口香糖中的应用。