2-(ethylthio)-4-isopropylthiazolone | 199447-34-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(ethylthio)-4-isopropylthiazolone
• 英文别名: 2-ethylsulfanyl-4-propan-2-yl-4H-1,3-thiazol-5-one
• CAS: 199447-34-2
• 化学式: C₈H₁₃NOS₂
• 分子量: 203.329
• InChiKey: YHBLUCJXEDDADN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(ethylthio)-4-isopropylthiazolone 在 盐酸 、 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1R)-(6-methoxyquinolin-4-yl)(8-vinylquinuclidin-2-yl)-methyl)thiourea 、 tin(ll) chloride 作用下， 以 乙醇 、 甲基叔丁基醚 、 水 为溶剂， 反应 12.0h， 生成 (S)-4-[(S)-2-amino-1-(4-methoxyphenyl)ethyl]-2-(ethylthio)-4-isopropylthiazol-5(4H)-one
  参考文献：
  名称：

  噻唑酮和硝基烯烃迈克尔反应的不对称有机催化方法：制备具有抗癌效力的化合物

  摘要：

  我们提出了一种高效的策略，通过创建碳和氮取代的季碳立体中心，获得一系列具有优异非对映选择性和对映选择性的手性 2,4-二取代噻唑酮衍生物。使用本课题组开发的手性叔胺硫脲催化剂，反应可以在1 mol-%的催化剂负载量下顺利进行，无需任何添加剂。初步生物学评价表明，这些类似物可以显着抑制体外细胞增殖。

  DOI：

  10.1002/ejoc.201201094
• 作为产物：
  描述：

  Sodium; (S)-2-dithiocarboxyamino-3-methyl-butyrate 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 2-(ethylthio)-4-isopropylthiazolone
  参考文献：
  名称：

  On the Tautomerism of 2,4-Disubstituted Thiazolones

  摘要：

  DOI：

  10.1002/1099-0690(20022)2002:3<557::aid-ejoc557>3.0.co;2-7

文献信息

• Asymmetric Aza-Mannich Addition: Synthesis of Modified Chiral 2-(Ethylthio)-thiazolone Derivatives with Anticancer Potency
  作者：Xiaodong Liu、Leijiao Deng、Hongjin Song、Huazhen Jia、Rui Wang

  DOI：10.1021/ol200185h

  日期：2011.3.18

  An easily prepared cinchona alkaloid derivative was found to be an effective organocatalyst in a direct, enantioselective aza-Mannich addition. By establishing a quaternary carbon stereocenter, a series of modified chiral 2-(ethylthio)-thiazolone derivatives have been obtained with excellent diastereo- and enantioselectivities. And these derivatives have been found to show anticancer activities against

  发现容易制备的金鸡纳生物碱衍生物在直接，对映选择性氮杂-曼尼希加成中是有效的有机催化剂。通过建立季碳立体中心，已获得了一系列具有出色的非对映异构和对映选择性的改性手性2-（乙硫基）-噻唑酮衍生物。并且使用MTT分析法已发现这些衍生物显示出对五种不同癌细胞系的抗癌活性。
• Synthesis of Symmetrical 2,2',4,4'-Tetrasubstituted [4,4'-Bithiazole]-5,5'(4H,4'H)-diones and Their Reactions with Some Nucleophiles.
  作者：Kenneth K. Andersen、Diana D. Bray、Anders Kjær、Yuhui Lin、Massud Shoja、E. Dooryhee

  DOI：10.3891/acta.chem.scand.51-1000

  日期：——

  Symmetrical 2,2',4,4'-tetrasubstituted-[4,4'-bithiazole]-5,5'(4H,4'H)-diones were obtained in high yields by oxidation of 5(4H)-thiazolones by KMnO4 in acetic acid. In some cases, the isomeric 2.4'- and 2,2'-bithiazolones were also formed. Results from two crossover reactions were consistent with a free radical mechanism. Four series of thiazolones were prepared, each based on a different substituent at the 2-position; i.e., phenyl, ethoxy, ethyl and ethylthio. The effects of substituents on the isomer distributions of the dehydrodimers indicated that electronic factors were less important than steric factors. X-Ray crystallography established the structure of the dehydrodimer (4R*,4'R*)-2,2'-diethoxy-4,4'dibenzyl-[4,4'-bithiazole]-5,5'(4H,4'H)-dione. One stereoisomer of 2,2'diphenyl-4,4'-dimethyl-[4,4'-bithiazole]-5,5'(4H,4'H)-dione and a mixture of the stereoisomers of 2,2'-diphenyl-4,4'-dibenzyl-[4,4'-bithiazole]-5,5'(4H,4'K)-dione were treated with nucleophiles. The former gave imide derivatives of alpha,alpha'-dehydrodimeric amino acids when the nucleophile was L-alanine ethyl ester or I-butylamine. The structure of one of the reaction products, (4R*,5R*)-2,5-diphenyl-2-thiazoline-4-carboxylic acid piperidylamide, was established by X-ray crystallography. Treatment of stereoisomeric mixtures of 2,2'-diethoxy-4,4'-bithiazolones with HCl in benzene gave the corresponding racemic and meso bis-(N-carboxythioanhydride)s. A stereoisomeric mixture of the bis(N-carboxythioanhydride)s of leucine treated with glycine ethyl ester gave a bicyclic derivative of the alpha,alpha'-dehydrodimeric amino acid.
• An Asymmetric Organocatalytic Approach to Michael Reactions of Thiazolones and Nitroalkenes: Preparation of Compounds with Anti-Cancer Potency
  作者：Xiaodong Liu、Hongjin Song、Qiao Chen、Wenyi Li、Wen Yin、Ming Kai、Rui Wang

  DOI：10.1002/ejoc.201201094

  日期：2012.10.9

  highly efficient strategy for obtaining a series of chiral 2,4-disubstituted thiazolone derivatives with excellent diastereo- and enantioselectivities through the creation of carbon- and nitrogen-substituted quaternary carbon stereocenters. With the chiral tertiary amine-thiourea catalyst developed by our group, the reactions could be performed smoothly at 1 mol-% catalyst loadings without any additive

  我们提出了一种高效的策略，通过创建碳和氮取代的季碳立体中心，获得一系列具有优异非对映选择性和对映选择性的手性 2,4-二取代噻唑酮衍生物。使用本课题组开发的手性叔胺硫脲催化剂，反应可以在1 mol-%的催化剂负载量下顺利进行，无需任何添加剂。初步生物学评价表明，这些类似物可以显着抑制体外细胞增殖。
• On the Tautomerism of 2,4-Disubstituted Thiazolones
  作者：Yuhui Lin、Kenneth K. Andersen

  DOI：10.1002/1099-0690(20022)2002:3<557::aid-ejoc557>3.0.co;2-7

  日期：2002.2