1-propanesulfinothioic acid S-(E)-1-propenyl ester | 119052-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代亚磺酸酯
• 英文名称: 1-propanesulfinothioic acid S-(E)-1-propenyl ester
• 英文别名: nPropyl-S(O)S-Propenyl；1-[(E)-prop-1-enyl]sulfanylsulfinylpropane
• CAS: 119052-98-1
• 化学式: C₆H₁₂OS₂
• 分子量: 164.293
• InChiKey: XLVMWOFYTFNDKM-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 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：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  反式丙烯基丙基二硫	Trans-propenyl-propyl-disulfid	23838-21-3	C6H12S2	148.293

反应信息

• 作为产物：
  描述：

  反式丙烯基丙基二硫 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-(E)-1-propenyl ester 、 (E)-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

文献信息

• PROCESS OF PREPARING CONJUGATES OF ALLIUM ORGANOSULFUR COMPOUNDS WITH AMINO ACIDS, PEPTIDES, AND PROTEINS
  申请人：Parkin Kirk L.

  公开号：US20110082282A1

  公开（公告）日：2011-04-07

  Processes using Allium tissue homogenates and extracts in a simple and cost-effective manner to maximize the yields and recovery of thiosulfinates from Allium tissues and related organisms possessing alliinase, LF synthase and/or S-alk(en)yl-L-cysteine sulfoxides are disclosed.

  本发明揭示了使用Allium组织匀浆和提取物的过程，以简单且经济有效的方式最大化从Allium组织和相关生物中具有alliinase、LF合成酶和/或S-烷基-L-半胱氨酸亚砜的硫代磺酸盐的产量和回收率。
• 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。
• US8481284B2
  申请人：——

  公开号：US8481284B2

  公开（公告）日：2013-07-09
• [EN] PROCESS OF PREPARING CONJUGATES OF ALLIUM ORGANOSULFUR COMPOUNDS WITH AMINO ACIDS, PEPTIDES, AND PROTEINS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CONJUGUÉS DE COMPOSÉS ORGANOSOUFRÉS D'ALLIUM AVEC DES ACIDES AMINÉS, DES PEPTIDES, ET DES PROTÉINES
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2011044113A1

  公开（公告）日：2011-04-14

  Processes using Allium tissue homogenates and extracts in a simple and cost-effective manner to maximize the yields and recovery of thiosulfinates from Allium tissues and related organisms possessing alliinase, LF synthase and/or S-alk(en)yl-L-cysteine sulfoxides are disclosed.
• <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).