S-methylsulfenyl O-methyl thiocarbonate | 55048-60-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 英文名称: S-methylsulfenyl O-methyl thiocarbonate
• 英文别名: (disulfido)carbonic acid dimethyl ester；Methoxycarbonylmethyldisulfid；Methylmethoxycarbonyldisulfid；methoxycarbonyl-methyl-disulfane；Methoxycarbonyl methyl disulfide；methyl (methyldisulfanyl)formate
• CAS: 55048-60-7
• 化学式: C₃H₆O₂S₂
• 分子量: 138.211
• InChiKey: FDGBKPKLBZGFKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 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：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  异戊烯基硫醇 、 S-methylsulfenyl O-methyl thiocarbonate 生成 methyl-(3-methyl-but-2-enyl)-disulfane
  参考文献：
  名称：

  Thiosulfoxides. Intermediates in rearrangement and reduction of allylic disulfides

  摘要：

  DOI：

  10.1021/ja00752a073
• 作为产物：
  描述：

  甲氧基二硫代甲酸甲酯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 S-methyl-O-methyl monothiocarbonate 、 S-methylsulfenyl O-methyl thiocarbonate
  参考文献：
  名称：

  Marriere, Eddie; Chevrie, David; Metzner, Patrick, Journal of the Chemical Society. Perkin transactions I, 1997, # 14, p. 2019 - 2020

  摘要：

  DOI：

文献信息

• Nuclear analogs of β -lactam antibiotics. IX. Synthesis of 7-methoxy 2-isocephems and <i>O</i>-2 isocephems
  作者：James L. Douglas、Donald E. Horning、Terry T. Conway

  DOI：10.1139/v78-473

  日期：1978.11.15

  The syntheses of 7-methoxy-7-phenoxyacetamido-3-methyl-Δ³-isocephem-4-carboxylic acid 11a, 7-methoxy-7-phenoxyacetamido-3-rnethyl- Δ³-O-2-isocephem-4-carboxylic acid 11b and 7-methoxy-7-(2-thienyl)acetamido-3-acetoxymethyl- Δ³-O-2-isocephem-4-carboxylic acid 11c are described. A sequence analogous to that used to prepare 7-methoxy cephalosporins was used: Schiff base anions were thiomethylated and the Schiff bases hydrolyzed to free amines. The amines were acylated and thiomethyl to methoxyl conversion effected with mercuric ion catalysis. Removal of protective esters gave the acids 11a, 11b, and 11c. Compound 11c showed a modest level but broad spectrum of antibacterial activity.

  描述了7-甲氧基-7-苯氧基乙酰胺基-3-甲基-Δ³-异头孢-4-羧酸11a、7-甲氧基-7-苯氧基乙酰胺基-3-甲基-Δ³-O-2-异头孢-4-羧酸11b和7-甲氧基-7-(2-噻吩基)乙酰胺基-3-乙酰氧甲基-Δ³-O-2-异头孢-4-羧酸11c的合成。使用了类似于制备7-甲氧基头孢菌素的序列：席夫碱负离子进行硫甲基化，然后将席夫碱水解成游离胺基。胺基被酰化，然后通过汞离子催化实现硫甲基到甲氧基的转化。去除保护酯基后得到酸11a、11b和11c。化合物11c显示出适度水平但广谱的抗菌活性。
• Synthesis of Novel Thiol-Containing Citric Acid Analogs. Kinetic Evaluation of These and Other Potential Active-Site-Directed and Mechanism-Based Inhibitors of ATP Citrate Lyase
  作者：Roland E. Dolle、Andy Gribble、Tracey Wilkes、Lawrence I. Kruse、Drake Eggleston、Barbara A. Saxty、Timothy N. C. Wells、Pieter H. E. Groot

  DOI：10.1021/jm00003a016

  日期：1995.2

  ATP citrate lyase is an enzyme involved in mammalian lipogenesis and cholesterogenesis. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agents. Citric acid analogues 5-16 bearing electrophilic and latent electrophilic substituents were synthesized and evaluated as irreversible inhibitors of the enzyme. The design of these agents was based on the classical enzymatic mechanism

  ATP柠檬酸裂合酶是一种参与哺乳动物脂肪生成和胆固醇生成的酶。该酶的抑制剂代表了潜在的新型降血脂药。合成带有亲电和潜在亲电取代基的柠檬酸类似物5-16，并评估为该酶的不可逆抑制剂。这些试剂的设计基于经典的酶机理，其中活性位亲核试剂（硫醇）被认为与催化反应密切相关。对于化合物5、10和12-16，观察到可逆的抑制作用（Ki's在约20至500μM的范围内）。化合物6-9和11对酶没有明显的亲和力（Ki> 1 mM）。在2 mM抑制剂浓度下长时间孵育（> 1 h，37摄氏度）后，未检测到5-16的时间依赖性酶失活。
• A general strategy for elaboration of the dithiocarbonyl functionality, -(C:O)SS-: application to the synthesis of bis(chlorocarbonyl)disulfane and related derivatives of thiocarbonic acids
  作者：George Barany、Alayne L. Schroll、Andrew W. Mott、David A. Halsrud

  DOI：10.1021/jo00172a056

  日期：1983.12
• Synthesis and structure-activity relationship of new cephalosporins with amino heterocycles at C-7. Dependence of the antibacterial spectrum and .beta.-lactamase stability on the pKa of the C-7 heterocycle
  作者：F. Jung、C. Delvare、D. Boucherot、A. Hamon、N. Ackerley、M. J. Betts

  DOI：10.1021/jm00107a035

  日期：1991.3

  Cephalosporins with new aminobenzimidazole and aminoimidazoline heterocycles at C-7 have been synthesized starting with versatile C-7 isocyanide dihalide synthons. The aminobenzimidazoles have a broad spectrum of antibacterial activity, including Gram-positive and Gram-negative organisms, but possess limited beta-lactamase stability. In contrast, the aminoimidazolines have a narrow spectrum of antibacterial activity, limited to Gram-negative strains only, but possess outstanding beta-lactamase stability. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-7 amino heterocycle, basic C-7 residues giving cephalosporins with exceptional beta-lactamase stability.
• Bentley,P.H. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 2455 - 2467
  作者：Bentley,P.H. et al.

  DOI：——

  日期：——