2-(4-甲基苯基)硫基乙酰胺 | 73623-29-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-(4-甲基苯基)硫基乙酰胺
• 英文名称: 2-(4-methylphenylsulfanyl)acetamide
• 英文别名: p-tolylsulfanyl-acetic acid amide；p-Tolylmercapto-essigsaeure-amid；C-p-Tolylmercapto-acetamid；ACETAMIDE, 2-(p-TOLYLTHIO)-；2-(4-methylphenyl)sulfanylacetamide
• CAS: 73623-29-7
• 化学式: C₉H₁₁NOS
• mdl: MFCD01671215
• 分子量: 181.258
• InChiKey: OUXWFAJIPHIEII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-甲基苯基)硫基乙酰胺 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 2-p-tolylsulfanyl-thioacetamide
  参考文献：
  名称：

  Identification of BR102910 as a selective fibroblast activation protein (FAP) inhibitor

  摘要：

  DOI：

  10.1016/j.bmcl.2021.127846
• 作为产物：
  描述：

  4-甲基苯硫基乙酸 在 氯化亚砜 、 氨 作用下， 生成 2-(4-甲基苯基)硫基乙酰胺
  参考文献：
  名称：

  亚砜在有机合成中的配体交换反应：生成α-氯代羧酸及其衍生物的烯醇镁的新方法

  摘要：

  在THF中用EtMgBr在低温下处理α-氯代α-亚磺酰基羧酸衍生物，得到α-氯代羧酸衍生物的烯醇镁。烯醇化物与酮和醛反应以高收率得到醛醇化合物（或α，β-环氧酸）。

  DOI：

  10.1016/s0040-4039(00)77606-4

文献信息

• Ligand exchange reaction of sulfoxides in organic synthesis: A novel method for generation of magnesium enolates and its application to synthesis of [α]-halocarboxylic acid derivatives and [α]-haloaldehydes
  作者：Tsuyoshi Satoh、Yasushi Kitoh、Ken-ichi Onda、Koji Takano、Koji Yamakawa

  DOI：10.1016/s0040-4020(01)90408-9

  日期：1994.4

  yields. The magnesium enolates derived from the α-chloro-α-sulfinyl acid derivatives were trapped with carbonyl compounds to afford the adducts, which were transformed to α, β-epoxy carboxylic acid derivatives. Thermal elimination of the sulfinyl group in the α-halo-α-sulfinyl acid derivatives and the α-halo-α-sulfinyl aldehydes gave α-halo-α, β-unsaturated carboxylic acid derivatives and α-halo-α,

  描述了一种合成α-卤代（C1，F）羧酸衍生物和α-卤代醛的新方法。α-卤代-α-亚磺酰基羧酸，酯和α-卤代-α-亚磺酰基醛分别容易地由芳基1-卤代烷基亚砜，氯代甲酸烷基酯和甲酸乙酯制备，产率高。由（对甲苯硫基）乙酸合成α-氯-α-亚磺酰基酰胺。这些酸，酯，酰胺和醛的亚磺酰基与乙基溴化镁的配体交换反应，得到了烯醇镁，将其用水处理后，以高收率得到α-卤代羧酸衍生物和α-氯醛。用羰基化合物捕获由α-氯代-α-亚磺酰基酸衍生物衍生的烯醇镁，以提供加合物，将其转化为α，β-环氧羧酸衍生物。
• Ligand exchange reaction of sulfoxides in organic synthesis: A new method for generation of magnesium enolates of α-chloro carboxylic acids and their derivatives
  作者：Tsuyoshi Satoh、Yasushi Kitoh、Ken-ichi Onda、Koji Yamakawa

  DOI：10.1016/s0040-4039(00)77606-4

  日期：1993.4

  Treatment of α-chloro α-sulfinyl carboxylic acid derivatives with EtMgBr in THF at low temperature gave magnesium enolates of the α-chloro carboxylic acid derivatives. The enolates reacted with ketones and aldehydes to afford aldol compounds (or α,β-epoxy acids) in good yields.

  在THF中用EtMgBr在低温下处理α-氯代α-亚磺酰基羧酸衍生物，得到α-氯代羧酸衍生物的烯醇镁。烯醇化物与酮和醛反应以高收率得到醛醇化合物（或α，β-环氧酸）。
• Nitrilase-catalysed hydrolysis of cyanomethyl p-tolyl sulfoxide: stereochemistry and mechanism
  作者：Piotr Kiełbasiński、Michał Rachwalski、Marian Mikołajczyk、Floris P.J.T. Rutjes

  DOI：10.1016/j.tetasy.2008.01.021

  日期：2008.3

  Several commercially available nitrilases have been used for the enantioselective hydrolysis of cyanomethyl p-tolyl sulfoxide into the corresponding amide and acid, which are formed in different proportions and with varying stereo selectivities, depending on the nitrilase involved. It was shown that the externally added amide is not transformed into the acid, which can be explained by assuming that both products must be produced in concurrent reactions. It was also demonstrated that the absolute configuration of the substrate exerts substantial influence on the product ratio. Two alternative explanations of the stereochemical course are presented. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of New (Arylsulfanyl)maleimide Derivatives
  作者：A. A. Panov、A. Yu. Simonov、A. M. Korolev

  DOI：10.1134/s1070428019120066

  日期：2019.12

  Previously unknown 2-(arylsulfanyl)-3-hydroxymaleimide and 2-(arylsulfanyl)-3-chloromaleimide derivatives have been synthesized, and several synthetic approaches to 2-(arylamino)-3-(arylsulfanyl)-maleimides have been tested. The reactivities of 2-chloro-3-(4-methylphenylsulfanyl)maleimide and 2,3-bis(4-methylphenylsulfanyl)maleimide toward nitrogen and sulfur nucleophiles have been studied, and products of substitution of one or two arylsulfanyl groups have been obtained.
• Baliah; Varadachari, Journal of the Indian Chemical Society, 1954, vol. 31, p. 666
  作者：Baliah、Varadachari

  DOI：——

  日期：——