methyl α-methylcinnamyl sulfide | 40486-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl α-methylcinnamyl sulfide
• 英文别名: trans-3-(Methylthio)-1-phenyl-1-butene；1-Methyl-3-phenylallyl Sulfide；trans-1-Methyl-3-phenyl-2-propenylmethylsulfide；[(E)-3-methylsulfanylbut-1-enyl]benzene
• CAS: 40486-72-4
• 化学式: C₁₁H₁₄S
• 分子量: 178.298
• InChiKey: KUZXJDOYGKOWKX-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  ethyl (E)-1-phenylbut-1-en-3-ol 生成 methyl α-methylcinnamyl sulfide
  参考文献：
  名称：

  Harano,K.; Taguchi,T., Chemical and pharmaceutical bulletin, 1972, vol. 20, p. 2348 - 2356

  摘要：

  DOI：

文献信息

• Stereoselective formation of allylic sulfides via two sequential (3,3)-sigmatropic rearrangements of allylic xanthates and its mechanistic aspects.
  作者：Kazunobu HARANO、Norihide OHIZUMI、Keisuke MISAKA、Shigeru YAMASHIRO、Takuzo HISANO

  DOI：10.1248/cpb.38.619

  日期：——

  O-(2-Alkynyl) S-alkyl dithiocarbonates (allylic xanthates) were pyrolyzed to give 2-alkenyl alkyl sulfides (allylic sulfides) via the corresponding allylically isomeric S-(2-alkenyl) S-alkyl dithiocarbonates. The reaction follows the first-order rate law with relatively low sensitivity to the ionizing power of the medium and sizeably negative entropies of activation. When a mixture of two dithiol esters having different S-(2-alkenyl) groups and different S-alkyl groups was pyrolyzed, a "cross product" was not observed. The reaction was found to be facilitated by the presence of phenolic compounds or Lewis acids.Based on these findings together with modified neglect of diatomic overlap (MNDO) calculation data, the mechanism for the formation reaction of 2-alkenyl alkyl sulfides is discussed.

  O-(2-炔基) S-烷基二硫代碳酸酯（烯丙基黄原酸酯）通过相应的烯丙异构S-(2-烯基) S-烷基二硫代碳酸酯，热解生成2-烯基烷基硫醚（烯丙基硫醚）。该反应遵循一级速率定律，对介质的电离能力相对不敏感，并且活化熵显著为负。当含有不同S-(2-烯基)基团和不同S-烷基基团的两种二硫酯混合物进行热解时，未观察到“交叉产物”。发现反应在酚类化合物或路易斯酸的存在下得到促进。基于这些发现以及改进的原子间重叠忽略（MNDO）计算数据，讨论了2-烯基烷基硫醚生成反应的机理。
• A convenient and stereoselective synthesis of allylic sulfides
  作者：Kazunobu Harano、Norihide Ohizumi、Takuzo Hisano

  DOI：10.1016/s0040-4039(00)98992-5

  日期：1985.1

  The fractional distillation of 0-(2-alkenyl or 2-cycloalkenyl) S-alkyl dithiocarbonates (xanthates) affords 2-alkenyl or 2-cycloalkenyl alkyl sulfides. The reaction involves the [3,3]-sigmatropic rearrangement of the xanthates to produce S-(2-alkenyl or 2-cycloalkenyl) S-alkyl dithiocarbonates followed by extrusion of carbon oxysulfide to give 2-alkenyl or 2-cycloalkenyl alkyl sulfides.

  0-（2-烯基或2-环烯基）S-烷基二硫代碳酸酯（黄原酸酯）的分馏得到2-烯基或2-环烯基烷基硫化物。该反应涉及黄原酸酯的[3，3]-σ重排，以产生S-（2-烯基或2-环烯基）S-烷基二硫代碳酸酯，随后挤出氧硫化碳，得到2-烯基或2-环烯基烷基硫化物。
• Activation and synthetic applications of thiostannanes. Protection of carboxyl groups with α-methylcinnamyl alcohol as a means of chemodifferentiation and selective activation
  作者：Tsuneo Sato、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/s0040-4039(00)99169-x

  日期：1989.1

  α-Methylcinnamyl (MEC) esters are converted into parent carboxylic acids under mild conditions, various functions being tolerated including acetoxy, siloxy, MEM, and so on. Furthermore, MEC esters are transformed into other esters through CsF-promoted alkylation of intermediary organotin carboxylates.

  在温和的条件下，α-甲基肉桂基（MEC）酯可转化为母体羧酸，可耐受多种功能，包括乙酰氧基，甲硅烷氧基，MEM等。此外，MEC酯通过CsF促进的中间有机锡羧酸酯的烷基化转化为其他酯。
• Activation and synthetic applications of thiostannanes. Deprotection and transformations of tetrahydropyranyl ethers
  作者：Tsuneo Sato、Junzo Otera、Hitosi Nozaki

  DOI：10.1021/jo00302a057

  日期：1990.7
• HARANO, KAZUNOBU;OHIZUMI, HORIHIDE;MISAKA, KEISUKE;YAMASHIRO, SHIGERU;HIS+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 619-624
  作者：HARANO, KAZUNOBU、OHIZUMI, HORIHIDE、MISAKA, KEISUKE、YAMASHIRO, SHIGERU、HIS+

  DOI：——

  日期：——