n-propyl trans-1-propenyl sulfide | 37981-35-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: n-propyl trans-1-propenyl sulfide
• 英文别名: 1t-propylsulfanyl-propene；1-Propenyl propyl sulfide；1-[(E)-prop-1-enyl]sulfanylpropane
• CAS: 37981-35-4
• 化学式: C₆H₁₂S
• 分子量: 116.227
• InChiKey: RKVNNVDQIVWRNA-HWKANZROSA-N

物化性质

• 沸点：
  144-145 °C
• 密度：
  0.859±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-(propylsulfanyl)propyne 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以81%的产率得到n-propyl trans-1-propenyl sulfide
  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

• Photoreduction de la benzophenone par des thioethers etudiee par pnic
  作者：G. Vermeersch、J. Marko、N. Febvay-Garot、S. Caplain、A. Couture、A. Lablache-Combier

  DOI：10.1016/0040-4020(78)88372-0

  日期：1978.1

  CIDNP (Chemically Induced Dynamic Nuclear Polarization) studies of the photoreduction of benzophenone by R-CH2-S-R' show evidence for the formation of vinylic deratives and adducts. The central intermediate in the reaction scheme is the radical pair R-CH-S-R' φ2-C-OHt. A study with selenides shows a different behaviour for these compounds.

  通过R-CH 2 -SR'对二苯甲酮进行光还原的CIDNP（化学诱导动态核极化）研究显示了乙烯基衍生物和加合物形成的证据。在反应方案中的中央中间是基团对R-CH-SR”φ 2 -C-OH吨。硒化物的研究显示了这些化合物的不同行为。
• ANTIFOULING COATING COMPOSITION
  申请人：Mitsubishi Chemical Corporation

  公开号：EP3284783A1

  公开（公告）日：2018-02-21

  A resin composition, formed to have a polymer (A) containing at least one monomer-derived structural unit having the structure represented by formula (1), (2) or (3) below, and after the resin composition is stored at 40°C for 30 days, the decomposition rate of the structure represented by formula (1), (2) or (3) in the polymer (A) is 20% or lower.

  一种树脂组合物，含有至少一种单体衍生结构单元的聚合物（A），该单体衍生结构单元具有下式（1）、（2）或（3）所代表的结构，且该树脂组合物在 40°C 下储存 30 天后，聚合物（A）中式（1）、（2）或（3）所代表结构的分解率为 20% 或更低。
• (METH)ACRYLIC COPOLYMER, METHOD FOR PRODUCING SAME, RESIN COMPOSITION AND ANTIFOULING PAINT COMPOSITION
  申请人：Mitsubishi Chemical Corporation

  公开号：EP3604364A1

  公开（公告）日：2020-02-05

  A (meth)acrylic copolymer of the present invention includes a constituent unit (B) derived from a polysiloxane block-containing polymerizable monomer (b) represented by Formula (b1). In Formula (b1), R30 represents a hydrogen atom or a methyl group, a represents an integer of 2 to 5, b represents a number of 0 to 50, c represents an integer of 0 to 18, d represents a number of 1 to 1000, e represents a number of 1 to 80, R31 to R39 each represents an alkyl group, an alkoxy group, a phenyl group, a substituted phenyl group, a phenoxy group, or a substituted phenoxy group.

  本发明的(甲基)丙烯酸共聚物包括由式(b1)代表的含聚硅氧烷嵌段可聚合单体(b)衍生的组成单元(B)。在式(b1)中，R30 代表氢原子或甲基，a 代表 2 至 5 的整数，b 代表 0 至 50 的整数，c 代表 0 至 18 的整数，d 代表 1 至 1000 的整数，e 代表 1 至 80 的整数，R31 至 R39 各自代表烷基、烷氧基、苯基、取代苯基、苯氧基或取代苯氧基。
• ANTIFOULING PAINT COMPOSITION
  申请人：Mitsubishi Chemical Corporation

  公开号：EP3805327A1

  公开（公告）日：2021-04-14

  An antifouling paint composition is provided, including: at least one compound (A) selected from the group consisting of compounds represented by Formula (1), Formula (2), and Formula (3); and a vinyl-based copolymer (B).

  提供了一种防污漆组合物，包括：至少一种选自由式（1）、式（2）和式（3）所代表的化合物组成的组的化合物（A）；以及乙烯基共聚物（B）。
• Mosquito activating formulations
  申请人：Commonwealth Scientific and Industrial Research Organisation

  公开号：US10701931B2

  公开（公告）日：2020-07-07

  The present invention relates to formulations useful for affecting the behaviour of mosquitoes. More specifically, the present invention relates to formulations for activating mosquitoes such as for attracting mosquitoes. The present invention further provides methods and dispensers incorporating these formulations. The formulation comprises a thio compound as the active, preferably a thioether such as allyl methyl sulphide (AMS), 1-methylthio-propane, 3-methylthio-propanol (MTPL), (E)-1-methylthio-1-propene, (Z)-1-methylthio-1-propene, or derivatives thereof.

  本发明涉及用于影响蚊子行为的制剂。更具体地说，本发明涉及用于激活蚊子的制剂，如用于吸引蚊子的制剂。本发明进一步提供了使用这些制剂的方法和分配器。制剂包括作为活性物的硫代化合物，最好是硫醚，如烯丙基甲基硫醚（AMS）、1-甲硫基丙烷、3-甲硫基丙醇（MTPL）、(E)-1-甲硫基-1-丙烯、(Z)-1-甲硫基-1-丙烯或其衍生物。

表征谱图