ethyl 3-methyl-3-benzylthiobutanoate | 377092-98-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-methyl-3-benzylthiobutanoate
• 英文别名: Butanoic acid, 3-methyl-3-[(phenylmethyl)thio]-, ethyl ester；ethyl 3-benzylsulfanyl-3-methylbutanoate
• CAS: 377092-98-3
• 化学式: C₁₄H₂₀O₂S
• 分子量: 252.378
• InChiKey: GKKAZRFKGYZTSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-methyl-3-benzylthiobutanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 3-benzylthio-3-methyl-1-butanol
  参考文献：
  名称：

  A novel tandem [4++2] cycloaddition–elimination reaction: 2-alkenyl-4,4-dimethyl-1,3-oxathianes as synthetic equivalents for α,β-unsaturated thioaldehydes

  摘要：

  The first tandem cationic [4(+)+2] polar cycloaddition-elimination reaction of 1-thia-1,3-butadienyl cations B with olefins to afford directly 3,4-dihydro-2H-thiopyrans D is described. The cations B were easily accessible by treatment of monothioacetals A, particularly the 2-alkenyl-4,4-dimethyl-1,3-oxathianes 1, with a hard Lewis acid. In this novel reaction, 2-alkenyl-4,4-dimethyl-1,3-oxathianes were utilized as synthetic equivalents for highly reactive alpha,beta-unsaturated thioaldehydes. The effect of geminal dimethyl substituents on the oxathianes 1 and the mechanistic aspect of the reaction are considered. The reaction's asymmetric version was also investigated using a chiral oxathiane 4 derived from (-)-(IR,2R,5R)-2-(I-mercapto-l-methylethyl)-5-methylcyclohexanol. Although the enantioselectivities were moderate, the whole process can be done under odorless conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00179-0
• 作为产物：
  描述：

  1-溴甲基-4-三甲基甲硅烷基-苯 在 四丁基氟化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 61.0h， 生成 ethyl 3-methyl-3-benzylthiobutanoate
  参考文献：
  名称：

  无臭硫醇和硫化物的开发及其在有机合成中的应用

  摘要：

  描述了新型无味硫醇（十二烷硫醇，4- 正 庚基苯基甲硫醇，4-三甲基甲硅烷基苯基甲硫醇，4-三甲基甲硅烷基苯硫醇）和无味硫化物（1-甲基硫烷基十二烷 ）的开发及其在脱烷基， 迈克尔 加成， Swern 氧化和 科里 - 金 氧化中的应用。 。

  DOI：

  10.1007/s00706-003-0122-1

文献信息

• Synthetic equivalents of benzenethiol and benzyl mercaptan having faint smell: odor reducing effect of trialkylsilyl group
  作者：Kiyoharu Nishide、Tetsuo Miyamoto、Kamal Kumar、Shin-ichi Ohsugi、Manabu Node

  DOI：10.1016/s0040-4039(02)02052-x

  日期：2002.11

  Syntheses and odor tests of the trialkylsilylated benzyl mercaptans and benzenethiols have revealed that the trimethylsilyl substituent on the benzene ring has a remarkable effect in reducing the foul smell of the parent benzyl mercaptan and benzenethiol. Protodesilylation allowed these silylated thiols to function as odorless synthetic equivalents of benzyl mercaptan and benzenethiol. This discovery will greatly improve the physical environment of the researcher working with these malodorous compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Development of Odorless Thiols and Sulfides and Their Applications to Organic Synthesis
  作者：Kiyoharu Nishide、Shin-ichi Ohsugi、Tetsuo Miyamoto、Kamal Kumar、Manabu Node

  DOI：10.1007/s00706-003-0122-1

  日期：2004.2.1

  Development of new odorless thiols (dodecanethiol, 4- n -heptylphenylmethanethiol, 4-trimethylsilylphenylmethanethiol, 4-trimethylsilylbenzenethiol) and an odorless sulfide (1-methylsulfanyldodecane) and their applications to dealkylation, Michael addition, Swern oxidation, and Corey - Kim oxidation are described.

  描述了新型无味硫醇（十二烷硫醇，4- 正 庚基苯基甲硫醇，4-三甲基甲硅烷基苯基甲硫醇，4-三甲基甲硅烷基苯硫醇）和无味硫化物（1-甲基硫烷基十二烷 ）的开发及其在脱烷基， 迈克尔 加成， Swern 氧化和 科里 - 金 氧化中的应用。 。
• A novel tandem [4++2] cycloaddition–elimination reaction: 2-alkenyl-4,4-dimethyl-1,3-oxathianes as synthetic equivalents for α,β-unsaturated thioaldehydes
  作者：Shin-ichi Ohsugi、Kiyoharu Nishide、Manabu Node

  DOI：10.1016/s0040-4020(03)00179-0

  日期：2003.3

  The first tandem cationic [4(+)+2] polar cycloaddition-elimination reaction of 1-thia-1,3-butadienyl cations B with olefins to afford directly 3,4-dihydro-2H-thiopyrans D is described. The cations B were easily accessible by treatment of monothioacetals A, particularly the 2-alkenyl-4,4-dimethyl-1,3-oxathianes 1, with a hard Lewis acid. In this novel reaction, 2-alkenyl-4,4-dimethyl-1,3-oxathianes were utilized as synthetic equivalents for highly reactive alpha,beta-unsaturated thioaldehydes. The effect of geminal dimethyl substituents on the oxathianes 1 and the mechanistic aspect of the reaction are considered. The reaction's asymmetric version was also investigated using a chiral oxathiane 4 derived from (-)-(IR,2R,5R)-2-(I-mercapto-l-methylethyl)-5-methylcyclohexanol. Although the enantioselectivities were moderate, the whole process can be done under odorless conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.