(mesyloxy)acetyl chloride | 3593-16-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (mesyloxy)acetyl chloride
• 英文别名: Methylsulfonyloxy-acetylchlorid；2-Chloro-2-oxoethyl methanesulfonate；(2-chloro-2-oxoethyl) methanesulfonate
• CAS: 3593-16-6
• 化学式: C₃H₅ClO₄S
• 分子量: 172.589
• InChiKey: YBAHFCASYBWQFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  (mesyloxy)acetyl chloride 在 羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 Methylsulfonyloxy-acetohydroxamsaeure
  参考文献：
  名称：

  Havbrandt,O.; Wachtmeister,C.A., Acta Chemica Scandinavica (1947), 1968, vol. 22, p. 2043 - 2044

  摘要：

  DOI：
• 作为产物：
  描述：

  (mesyloxy)acetic acid 在 氯化亚砜 作用下， 生成 (mesyloxy)acetyl chloride
  参考文献：
  名称：

  Havbrandt,O.; Wachtmeister,C.A., Acta Chemica Scandinavica (1947), 1968, vol. 22, p. 2043 - 2044

  摘要：

  DOI：

文献信息

• β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives
  作者：Thomas Storz、Bruno Bernet、Andrea Vasella

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2380::aid-hlca2380>3.0.co;2-p

  日期：1999.12.15

  The D-manno-configured N-anisylated beta-lactam 40, the beta-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from D-glucose in 8-10 steps, respectively None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the D-erythroses 6, 16, and 17 with the ketene: from mesyloxyacetyl chloride (20) gave the 2-mesyloxy-D-hexono-1,3-lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (> 85%) to the corresponding azides, followed by oxidative N-deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N-atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl)phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the beta-lactam amino acid 43, besides its hydrolysis product 44. Reductive N-acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2-trifluoroacetamido N-(carboxymethyl)-beta-lactam 4 (56%). Similarly, 47 gave the 2-trifluoroacetamide 48 (89%), and hence, the 2-amino-N-(phosphonoylmethyl)-beta-lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected beta-lactams 31a and 35 led to the 2,3-diamino-2,3-dideoxy-D-mannonamides 51 and 53, respectively (Scheme 6).
• Phan; Miskolczi; Sztaricskai, Acta Chimica Academiae Scientiarum Hungaricae, 1980, vol. 103, # 4, p. 415 - 420
  作者：Phan、Miskolczi、Sztaricskai、Bognar

  DOI：——

  日期：——
• Havbrandt,O.; Wachtmeister,C.A., Acta Chemica Scandinavica (1947), 1968, vol. 22, p. 2043 - 2044
  作者：Havbrandt,O.、Wachtmeister,C.A.

  DOI：——

  日期：——