ethyl 2-(thiophen-2-ylthio)propanoate | 60493-14-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-(thiophen-2-ylthio)propanoate
• 英文别名: ethyl 2-(2-thienylthio)-propionate；ethyl 2-(thien-2-ylthio)-propionate；Ethyl 2-thiophen-2-ylsulfanylpropanoate
• CAS: 60493-14-3
• 化学式: C₉H₁₂O₂S₂
• 分子量: 216.325
• InChiKey: BPOKPXVWCPYDPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(thiophen-2-ylthio)propanoate 在 peroxodisulfate ion 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(thiophene-2-sulfonyl)-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of α-Sulfonylhydroxamic Acids as Novel, Orally Active Matrix Metalloproteinase Inhibitors for the Treatment of Osteoarthritis

  摘要：

  The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. These enzymes are strictly regulated by endogenous inhibitors such as tissue inhibitors of MMPs and alpha(2)-macroglobulins. Overexpression of these enzymes has been implicated in various pathological disorders such as arthritis, tumor metastasis, cardiovascular diseases, and multiple sclerosis. Developing effective small-molecule inhibitors to modulate MMP activity is one approach to treat these degenerative diseases. The present work focuses on the discovery and SAR of novel N-hydroxy-alpha-phenylsulfonylacetamide derivatives, which are potent, selective, and orally active MMP inhibitors.

  DOI：

  10.1021/jm0205548
• 作为产物：
  描述：

  2-甲基乙酰乙酸乙酯 、 2-氨基苯硫醇 在 氧气 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以75%的产率得到ethyl 2-(thiophen-2-ylthio)propanoate
  参考文献：
  名称：

  通过顺序的3-氧代丁酸酰胺/酯的氧化亚磺酰基化和CC键裂解，可直接获得α-亚磺酰化的酰胺/酯

  摘要：

  在氧气气氛下，已经开发出一种高效，环境友好的和前所未有的合成各种α-亚磺酰化酰胺/酯的方法。该反应显示出良好的官能团耐受性和优异的化学/区域选择性。即使在克规模上，也以中等至极好的收率获得了所有所需的产品。实际上，相关的α-硫醇Weinreb酰胺可以很容易地转移到一系列预期的化合物中，并且硒原子可以高产率地引入到酰胺的α-位。

  DOI：

  10.1039/c7cc09026a

文献信息

• Novel thiophene derivatives and their preparation
  申请人：Schering Aktiengesellschaft

  公开号：US04031236A1

  公开（公告）日：1977-06-21

  Thiophene derivatives of the formula ##STR1## IN WHICH R.sub.x is --S--CHR.sub.5 --CONHOH or --S--CHR.sub.5 -5-tetrazolyl in which R.sub.5 is H or alkyl of 1-6 carbon atoms and R.sub.y is 0-2 of alkyl or alkoxy of 1-6 carbon atoms or halogen, and their pharmacologically acceptable salts with bases, possess antilipolytic activity.

  Thiophene衍生物的公式为##STR1##其中R.sub.x为--S--CHR.sub.5 --CONHOH或--S--CHR.sub.5 -5-四唑基，其中R.sub.5为H或1-6碳原子的烷基，R.sub.y为1-6碳原子的烷基、烷氧基或卤素，以及它们与碱形成的药理学上可接受的盐具有抗脂解活性。
• US4031236A
  申请人：——

  公开号：US4031236A

  公开（公告）日：1977-06-21
• Direct access to α-sulfenylated amides/esters <i>via</i> sequential oxidative sulfenylation and C–C bond cleavage of 3-oxobutyric amides/esters
  作者：Yi Jiang、Jie-dan Deng、Hui-hong Wang、Jiao-xia Zou、Yong-qiang Wang、Jin-hong Chen、Long-qing Zhu、Hong-hua Zhang、Xue Peng、Zhen Wang

  DOI：10.1039/c7cc09026a

  日期：——

  An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred

  在氧气气氛下，已经开发出一种高效，环境友好的和前所未有的合成各种α-亚磺酰化酰胺/酯的方法。该反应显示出良好的官能团耐受性和优异的化学/区域选择性。即使在克规模上，也以中等至极好的收率获得了所有所需的产品。实际上，相关的α-硫醇Weinreb酰胺可以很容易地转移到一系列预期的化合物中，并且硒原子可以高产率地引入到酰胺的α-位。
• Synthesis and Structure−Activity Relationship of α-Sulfonylhydroxamic Acids as Novel, Orally Active Matrix Metalloproteinase Inhibitors for the Treatment of Osteoarthritis
  作者：Venkatesan Aranapakam、George T. Grosu、Jamie M. Davis、Baihua Hu、John Ellingboe、Jannie L. Baker、Jerauld S. Skotnicki、Arie Zask、John F. DiJoseph、Amy Sung、Michele A. Sharr、Loran M. Killar、Thomas Walter、Guixian Jin、Rebecca Cowling

  DOI：10.1021/jm0205548

  日期：2003.6.1

  The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. These enzymes are strictly regulated by endogenous inhibitors such as tissue inhibitors of MMPs and alpha(2)-macroglobulins. Overexpression of these enzymes has been implicated in various pathological disorders such as arthritis, tumor metastasis, cardiovascular diseases, and multiple sclerosis. Developing effective small-molecule inhibitors to modulate MMP activity is one approach to treat these degenerative diseases. The present work focuses on the discovery and SAR of novel N-hydroxy-alpha-phenylsulfonylacetamide derivatives, which are potent, selective, and orally active MMP inhibitors.