S-(2-sulfanylethyl) 3-oxobutanoate | 122279-99-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: S-(2-sulfanylethyl) 3-oxobutanoate
• 英文别名: 2-mercapto ethyl-3-oxo butanoate；mercaptoethylacetoacetate；thioethyl acetoacetate；Butanoic acid, 3-oxo-, 2-mercaptoethyl ester；2-sulfanylethyl 3-oxobutanoate
• CAS: 122279-99-6
• 化学式: C₆H₁₀O₃S
• 分子量: 162.21
• InChiKey: QXUCUVZHYIRQTP-UHFFFAOYSA-N

物化性质

• 沸点：
  110-115 °C(Press: 5 Torr)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-巯基乙醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以89%的产率得到S-(2-sulfanylethyl) 3-oxobutanoate
  参考文献：
  名称：

  Chemoselective Transesterification of β-Keto Esters under Neutral Conditions using NBS as a Catalyst

  摘要：

  简便且选择性的β-酮酯转酯化反应，采用N-溴代琥珀酰亚胺（NBS）作为高效中性的催化剂，这一方法已被描述。

  DOI：

  10.1055/s-2001-18082

文献信息

• The importance of the amide bond nearest the thiol group in enzymatic reactions of coenzyme A
  作者：Jin Xun、Haidong Huang、Kurt W. Vogel、Dale G. Drueckhammer

  DOI：10.1016/j.bioorg.2004.10.002

  日期：2005.4

  Analogues of coenzyme A (CoA) and of CoA thioesters have been prepared in which the amide bond nearest the thiol group has been modified. An analogue of acetyl-CoA in which this amide bond is replaced with an ester linkage was a good substrate for the enzymes carnitine acetyltransferase, chloramphenicol acetyltransferase, and citrate synthase, with K(m) values 2- to 8-fold higher than those of acetyl-CoA

  已经制备了辅酶A（CoA）和CoA硫酯的类似物，其中最接近硫醇基的酰胺键已被修饰。其中的酰胺键被酯键取代的乙酰基-CoA的类似物是肉碱乙酰基转移酶，氯霉素乙酰基转移酶和柠檬酸合酶的良好底物，其K（m）值比后者高2至8倍。乙酰基CoA和V（max）值是天然底物的14％至> 80％。在酰胺键和硫醇基团之间插入了额外亚甲基的类似物，与三种酶的结合力降低了不到4倍，但相对于带有肉碱乙酰基转移酶的乙酰辅酶A而言，活性却低于1％，而对乙酰辅酶A则没有可测量的活性。其他两种酶。几种CoA硫酯的类似物（其中酰胺键被半硫缩醛键取代）没有显示出用适当的酶可测量的活性。结果表明，酰胺键的某些方面以及该酰胺与硫醇/硫酯部分之间的适当距离对于利用CoA酯的酶的活性至关重要。
• A Facile and Selective Procedure for Transesterification of β-Keto Esters Promoted by Yttria-Zirconia Based Lewis Acid Catalyst
  作者：Pradeep Kumar、Rajesh Kumar Pandey

  DOI：10.1055/s-2000-6496

  日期：2000.2

  An yttria-zirconia based strong Lewis acid efficiently catalyses the transesterification of β-keto esters under environmentally safe, heterogeneous reaction conditions with high selectivity and in good to excellent yields.

  一种基于钇锆的强路易斯酸可在环境安全的异构反应条件下高效催化δ-酮酯的酯交换反应，具有高选择性和良好甚至优异的产率。
• METHOD OF LABELING SULFENIC ACID-CONTAINING PROTEINS AND PEPTIDES
  申请人：Wake Forest University Health Sciences

  公开号：US20150346209A1

  公开（公告）日：2015-12-03

  A method of labeling a sulfenic acid (—SOH) group of a cysteine residue in a protein or peptide, comprises contacting said protein or peptide with a beta-ketoester to covalently couple said beta-ketoester to said cysteine residue and form a beta-ketoester-labeled cysteine residue in said protein or peptide.

  一种标记蛋白质或肽中半胱氨酸残基的磺酰基（—SOH）的方法，包括将所述蛋白质或肽与β-酮酸酯接触，使β-酮酸酯共价耦合到所述半胱氨酸残基上，并在所述蛋白质或肽中形成一个β-酮酸酯标记的半胱氨酸残基。
• Mercaptoalkyl acetoacetates
  申请人：Rohm and Haas Company

  公开号：US04960924A1

  公开（公告）日：1990-10-02

  This invention relates to mercaptoalkyl acetoacetates and a process for preparing mercaptoalkyl acetoacetates. The process embraces the reaction of TKD (a diketene-acetone adduct) with hydroxy-functional mercaptans. Preferred is the reaction of TKD with 2-mercaptoethanol to yield mercaptoethyl acetoacetate. Mercaptoethyl acetoacetate is an effective chain transfer agent in free radical polymerization reactions with the benefit of introducing reactive acetoacetate functionally into the formed polymer.

  本发明涉及巯基烷基乙酰乙酸酯及其制备方法。该方法包括将TKD（二羰基-丙酮加合物）与羟基官能基巯基反应。首选是将TKD与2-巯基乙醇反应，得到巯基乙基乙酰乙酸酯。巯基乙基乙酰乙酸酯在自由基聚合反应中是一种有效的链转移剂，具有将反应性乙酰乙酸酯功能引入形成的聚合物的优点。
• Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay
  作者：Datta E. Ponde、Vishnu H. Deshpande、Vivek J. Bulbule、Arumugam Sudalai、Anil S.Gajare

  DOI：10.1021/jo971404l

  日期：1998.2.1

  Transesterification and transthiolesterification of beta-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding beta-keto esters in high yields. For the first time, transthiolesterification of beta-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of beta-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding beta-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward beta-keto esters is also described. Sterically hindered carbonyl groups as well as alpha,beta-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.