(E)-1-allyl-2-(prop-1-en-1-yl) disulfane | 122156-02-9

• 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: (E)-1-allyl-2-(prop-1-en-1-yl) disulfane
• 英文别名: Allyl prop-1-enyl disulfide；(E)-1-(prop-2-enyldisulfanyl)prop-1-ene
• CAS: 122156-02-9
• 化学式: C₆H₁₀S₂
• 分子量: 146.277
• InChiKey: KBXOGESWPIVMNJ-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-allyl-2-(prop-1-en-1-yl) disulfane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-propene-1-sulfinothioic acid S-(E)-1-propenyl ester 、 (E)-1-propenesulfinothioic acid S-2-propenyl 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：

  烯丙基二甲基砜 、 n-propyl trans-1-propenyl sulfide 在 氨 、 lithium 作用下， 生成 (E)-1-allyl-2-(prop-1-en-1-yl) disulfane
  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

• Furfuryl propyl disulfide as a flavoring agent and methods for preparing and using same
  申请人：——

  公开号：US20020110628A1

  公开（公告）日：2002-08-15

  This invention pertains to a method for flavoring an ingestible composition with a flavoring agent, furfuryl propyl disulfide, in organoleptically purified form, unaccompanied by substances of natural origin present in cooked beef and onions. The flavoring agent may be used in a wide variety of ingestible vehicles to augment or enhance the aroma or taste of foodstuffs, particularly roasted nut, roasted meat, beef broth, black pepper, onion, fine herbs, omelet, and cooked onion omelet flavored foodstuffs. The present invention also pertains to an ingestible composition comprising an ingestible vehicle and an organoleptically effective amount of the purified flavoring agent. The present invention also pertains to furfuryl propyl disulfide represented by the formula, (2-Furan-CH 2 SSCH 2 CH 2 CH 3 ), in purified form, unaccompanied by substances of natural origin present in cooked beef and onions, and to methods for preparing furfuryl propyl disulfide.

  本发明涉及一种用味道剂味化可食用组合物的方法，所述味道剂为味觉上纯化的呋喃基丙基二硫化物，不含烹煮牛肉和洋葱时存在的天然物质。该味道剂可用于各种可食用载体中，以增强或提高食物的香气或口感，特别是烤坚果、烤肉、牛肉汤、黑胡椒、洋葱、香料、煎蛋和煮洋葱煎蛋调味食品。本发明还涉及一种包含可食用载体和纯化的味道剂的味道组合物。本发明还涉及用公式表示的呋喃基丙基二硫化物（2-呋喃-CH2SSCH2CH2CH3）的纯化形式，不含烹煮牛肉和洋葱时存在的天然物质，以及制备呋喃基丙基二硫化物的方法。
• Artifically flavoured edible oils or fats
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0021481A1

  公开（公告）日：1981-01-07

  A partially encapsulated flavor is disclosed. Specific volatile components of the flavor which have offensive odors are encapsulated in an oil-insoluble material. The remaining, less volatile components are not encapsulated. This partially encapsulated flavor is particularly useful for flavoring foods such as edible oils and cooking oils. Also disclosed is a water-soluble flavorant in which specific volatile components having offensive odors are encapsulated in a water-insoluble material. The remaining less-volatile components are not encapsulated.

  本发明公开了一种部分封装的香精。香精中具有刺激性气味的特定挥发性成分被封装在一种不溶于油的材料中。其余挥发性较低的成分则未被封装。这种部分封装的香精特别适用于食用油和烹调油等食品的调味。 还公开了一种水溶性香料，其中具有刺激性气味的特定挥发性成分被封装在不溶于水的材料中。其余挥发性较低的成分不被封装。
• EP1280419A4
  申请人：——

  公开号：EP1280419A4

  公开（公告）日：2005-01-19
• FURFURYL PROPYL DISULFIDE AS A FLAVORING AGENT AND METHODS FOR PREPARING AND USING SAME
  申请人：Bush Boake Allen Inc.

  公开号：EP1280419A1

  公开（公告）日：2003-02-05
• US4504508A
  申请人：——

  公开号：US4504508A

  公开（公告）日：1985-03-12