2-(2',2'-Diethoxyethylthio)acetamide | 72619-11-5

• 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-(2',2'-Diethoxyethylthio)acetamide
• 英文别名: 2-<(2,2-diethoxyethyl)thio>acetamide；(2,2-Diethyloxyethylthio)acetamide；2-(2, 2-diethoxyethylthio)acetamide；2-(2,2-diethoxyethylthio)acetamide；2-(2,2-diethoxyethylsulfanyl)acetamide
• CAS: 72619-11-5
• 化学式: C₈H₁₇NO₃S
• 分子量: 207.294
• InChiKey: TVHDBNXUOLUDPA-UHFFFAOYSA-N

物化性质

• 沸点：
  334.2±42.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2',2'-Diethoxyethylthio)acetamide 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以92%的产率得到3,4-dihydro-3-oxo-2H-[1,4]thiazin
  参考文献：
  名称：

  橄榄酸类似物的合成。含3-（2-乙酰氨基乙硫基）侧链的7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸酯的制备

  摘要：

  由4-羧甲基氮杂环丁烷-2-酮制备2-乙酰氨基乙烯基硫代酸酯，并通过分子内Wittig反应环化以提供3-（2-乙酰氨基乙烯基硫代）-7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2 -羧酸盐，与天然存在的抗生素MM 13902（1）密切相关的类似物。

  DOI：

  10.1039/c39800000429
• 作为产物：
  描述：

  ethyl 2-<(2,2-diethoxyethyl)thio>acetate 在 氨 作用下， 以 甲醇 为溶剂， 以95%的产率得到2-(2',2'-Diethoxyethylthio)acetamide
  参考文献：
  名称：

  Nucleosides of 1,4-thiazin-3-one and derivatives as tetrahedral intermediate analogs of enzymes in pyrimidine nucleoside metabolism

  摘要：

  Reaction of the trimethylsilylated derivative of 1,4-thiazin-3-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose in the presence of SnCl4 gave, after deblocking, 4-beta-ribofuranosyl-1,4-thiazin-3-one (8). Treatment of 1,4-thiazin-3-one with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose in the presence of sodium hydride provided, after deblocking, the corresponding 2-deoxy-beta-D-ribofuranosyl derivatives (19). Oxidation of 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one (7) with 1 equiv of m-chloroperbenzoic acid resulted in 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazine-2,3-dione (9) and 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one 1-oxide (10). Evidence is presented that indicates that the oxidation of the thiazine at the 2-position is due to a Pummerere rearrangement. The new compounds failed to show significant activity against tumor cell lines in culture, L1210 cells in vivo, virus cytotoxicity in cell culture, or cytidine deaminase.

  DOI：

  10.1021/jm00403a015

文献信息

• Synthesis of olivanic acid analogues. Preparation of 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylates containing the 3-(2-acetamidoethenylthio) side chain
  作者：Andrew J. G. Baxter、Roger J. Ponsford、Robert Southgate

  DOI：10.1039/c39800000429

  日期：——

  2-Acetamidoethenylthioesters have been prepared from 4-carboxymethylazetidin-2-one and cyclised via an intramolecular Wittig reaction to provide 3-(2-acetamidoethenylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylates, closely related analogues of the naturally occurring antibiotic MM 13902 (1).

  由4-羧甲基氮杂环丁烷-2-酮制备2-乙酰氨基乙烯基硫代酸酯，并通过分子内Wittig反应环化以提供3-（2-乙酰氨基乙烯基硫代）-7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2 -羧酸盐，与天然存在的抗生素MM 13902（1）密切相关的类似物。
• Clavulanic acid derivatives their preparation and use
  申请人：Beecham Group Limited

  公开号：US04372962A1

  公开（公告）日：1983-02-08

  The compounds of the formula (I): ##STR1## and pharmaceutically acceptable salts and in-vivo hydrolysable esters thereof wherein X is a sulphur atom or SO or SO.sub.2 group and R is a hydrogen atom or an alkyl group of 1 to 6 carbon atoms have been found to be .beta.-lactamase inhibitors and antibacterial agents. Their preparation and use is described.

  化合物的化学式（I）：##STR1##及其药用盐和体内可水解酯，其中X是硫原子或SO或SO.sub.2基团，R是氢原子或1至6个碳原子的烷基基团，已被发现是β-内酰胺酶抑制剂和抗菌剂。它们的制备和用途已经描述。
• Synthesis of 2<i>H</i>-1,4-thiazin-3(4<i>H</i>)-one 1-oxide and 2<i>H</i>-1,4-thiazin-3-(4<i>H</i>)-one 1,1-dioxide, structural analogs of uracil
  作者：M. Bobek

  DOI：10.1002/jhet.5570190125

  日期：1982.1

  The synthesis of 1,4-thiazine 1-oxide and 1,1-dioxide analogs of the antibiotic emimycin is described. Reaction of methylthioglycolate with 1-bromo-2,2-diethoxyethane gave methyl (2,2-diethoxyethylthio)acetate (2). Treatment of 2 with methanolic ammonia followed by cyclization furnished 2H-1,4-thiazin-3(4H)-one (5). Oxidation of 5 with m-chloroperoxybenzoic acid converted it to 2H-1,4-thiazin-3(4H)-one

  描述了抗生素阿米霉素的1,4-噻嗪1-氧化物和1,1-二氧化物类似物的合成。甲基硫代乙醇酸酯与1-溴-2,2-二乙氧基乙烷的反应，得到（2,2-二乙氧基乙基硫基）乙酸甲酯（2）。用甲醇氨处理2，然后环化，得到2 H -1，4-噻嗪-3（4 H）-一（5）。氧化5与米氯过氧酸转换它为2 ħ -1,4-噻嗪-3（4 H ^） -酮1-氧化物（6）。用高锰酸钾氧化2，然后用甲醇氨处理，环化得到2 H-1,4-噻嗪-3（4 H）-1,1-二氧化物。
• Novel thiazine derivatives
  申请人：SANTEN PHARMACEUTICAL CO.,LTD.

  公开号：US20040097496A1

  公开（公告）日：2004-05-20

  A compound having 3-oxo-3,4-dihydro-2H-1,4-thiazine 4-tetrahydropyrazine as a main skeleton. The compound is a chymase inhibitor and is represented by the following formula [I] and salts thereof: 1 In the formula [I], X is S; R 1 and R 2 are H, alkyl, cycloalkyl or aryl; R 3 and R 4 are H, alkyl, cycloalkyl, aryl or an aromatic heterocycle; R 5 is H, alkyl, cycloalkyl, aryl or -A 3 -A 4 -R 7 ; R 6 is H, alkyl, cycloalkyl, hydroxy, alkoxy, aryl, aryloxy or an aromatic heterocycle; R 7 is H, alkyl, hydroxy, alkoxy, aryl, aryloxy, amino, alkylamino, arylamino, an aromatic heterocycle or a nonaromatic heterocycle; A 1 is alkylene; A 2 is carbonyl or sulfonyl; A 3 is alkylene; A 4 is carbonyl or oxalyl; and n is 0 or 1.

  化合物具有3-氧代-3,4-二氢-2H-1,4-噻嗪-4-四氢吡嗪作为主要骨架。该化合物是一种Chymase抑制剂，由以下公式[I]及其盐所表示：1在公式[I]中，X为S；R1和R2为H，烷基，环烷基或芳基；R3和R4为H，烷基，环烷基，芳基或芳香族杂环；R5为H，烷基，环烷基，芳基或-A3-A4-R7；R6为H，烷基，环烷基，羟基，烷氧基，芳基，芳氧基或芳香族杂环；R7为H，烷基，羟基，烷氧基，芳基，芳氧基，氨基，烷基氨基，芳基氨基，芳香族杂环或非芳香族杂环；A1为烷基；A2为羰基或磺酰基；A3为烷基；A4为羰基或草酰基；n为0或1。
• Beta-lactam antibiotics, a process for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0003740A2

  公开（公告）日：1979-09-05

  The present invention provides the antibacterial agents of the formula (II): Wherein R1 is a group such that CO2R1 is a carboxylic acid group or a salt thereof or is a group of the formula CO2R wherein is a group such that CO2 is an ester group, R2 is a hydrogen atom or a lower alkyl group; R3 is a hydrogen atom or a lower alkyl group; and R4 is a phenyl group or a phenyl group substituted by one or two groups selected from fluorine, chlorine, OR5, NH.CO.R5, NH.CO2R5 or C02Rs where Rs is a lower alkyl or benzyl group or R4 is a hydrogen atom or lower alkyl group or R4 is a CO2R5 group where Rs is a lower alkyl group or benzyl group or R4 is a NH.COnRe group where R6 is a lower alkyl group, a phenyl group or a phenyl group substituted by one or two halogen atoms, lower alkyl or lower alkoxyl groups: and n is 1 or 2. A process for their preparation and their use in pharmaceutical compositions is also described.

  本发明提供了式(II)的抗菌剂： 其中 R1 是 CO2R1 是羧酸基团或其盐的基团，或者是式 CO2R 的基团，其中 R1 是 CO2 是酯基的基团；R2 是氢原子或低级烷基；R3 是氢原子或低级烷基；R4 是苯基或被选自氟、氯、OR5、NH.CO.R5、NH.CO2R5 或 C02Rs 的一个或两个基团取代的苯基。CO.R5、NH.CO2R5或C02Rs，其中Rs是低级烷基或苄基，或R4是氢原子或低级烷基，或R4是CO2R5基团，其中Rs是低级烷基或苄基，或R4是NH.COnRe基团，其中R6是低级烷基、苯基或被一个或两个卤素原子、低级烷基或低级烷氧基取代的苯基：且n是1或2。此外，还介绍了它们的制备过程及其在药物组合物中的用途。