ethyl 2-methyl-2-thiocyanato-3-oxobutanoate | 156498-53-2

• 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: ethyl 2-methyl-2-thiocyanato-3-oxobutanoate
• 英文别名: ethyl 2-methyl-2-thiocyanatoacetoacetate；Ethyl 2-methyl-3-oxo-2-thiocyanatobutanoate
• CAS: 156498-53-2
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: UITYPFRTOVIKND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异硫氢酸三甲基硅酯 以69%的产率得到
  参考文献：
  名称：

  Tanabe Yoo, Makita Takuya, Mori Kei, Chem. Lett, (1994) N 12, S 2275-2278

  摘要：

  DOI：

文献信息

• α-Thiocyanation of Carbonyl and β-Dicarbonyl Compounds Using (Dichloroiodo)benzene−Lead(II) Thiocyanate
  作者：Om Prakash、Harpreet Kaur、Hitesh Batra、Neena Rani、Shiv P. Singh、Robert M. Moriarty

  DOI：10.1021/jo001504i

  日期：2001.3.1

  combination reagent (dichloroiodo)benzene and lead(II) thiocyanate in dichloromethane effects oxidation of various enol silyl ethers, ketene silyl acetals, and beta-dicarbonyl compounds, thereby providing an efficient and convenient method for alpha-thiocyanation of carbonyl and beta-dicarbonyl compounds.

  二氯甲烷中的（二氯碘代）苯和硫氰酸铅（II）的组合试剂可实现各种烯醇甲硅烷基醚，乙烯酮甲硅烷基乙缩醛和β-二羰基化合物的氧化，从而为羰基和β-二羰基的α-硫氰化提供了一种有效而便捷的方法化合物。
• One-Pot Synthesis Using Supported Reagents System: Conversion of β-Dicarbonyl Compounds to α-Thiocyano-β-dicarbonyl Compounds Using CuBr₂/Al₂O₃-KSCN/SiO₂
  作者：Yoshitada Suzuki、Mitsuo Kodomari

  DOI：10.1246/cl.1998.1091

  日期：1998.11

  Transformation of β-dicarbonyl compound 1 to α-thiocyano-β-dicarbonyl compounds 3 in one-pot was achieved by using supported reagents system CuBr2/Al2O3-KSCN/SiO2, in which 1 reacts first with CuBr2/Al2O3 and the product, α-bromo-β-dicarbonyl compound 2 reacts with KSCN/SiO2 to give the final product 3 in good yield.

  β-二羰基化合物 1 在一锅法中转化为 α-硫氰基-β-二羰基化合物 3 是通过使用负载试剂系统 CuBr2/Al2O3-KSCN/SiO2 实现的，其中 1 首先与 CuBr2/Al2O3 和产物 α 反应-溴-β-二羰基化合物 2 与 KSCN/SiO2 反应，以良好的收率得到最终产物 3。
• Direct and Electrophilic Preparation of α-Thiocyanatoketones and Aldehydes Using Thiocyanatotrimethylsilane and Sulfuryl Chloride
  作者：Yoo Tanabe、Takuya Makita、Kei Mori

  DOI：10.1246/cl.1994.2275

  日期：1994.12

  The thiocyanato (-SCN) group was directly and regioselectively introduced into the α-position of ketones, aldehydes, and aldols in an electrophilic manner by the combined use of thiocyanatotrimethylsilane and sulfuryl chloride with or without cyclic sec-amine catalysts under mild reaction conditions.

  硫氰酸根（-SCN）通过结合使用硫氰基三甲基硅烷和氯化硫酰，在温和的反应条件下，直接且区域选择性地以电亲和的方式引入到酮、醛和醇类的α位。可选使用或不使用环状二级胺催化剂。
• Pseudohalogen chemistry. XI. Some aspects of the chemistry of α-thiocyanato-β-dicarbonyl compounds
  作者：Elaine F. Atkins、Steven Dabbs、Robert G. Guy、Akbar A. Mahomed、Philip Mountford

  DOI：10.1016/s0040-4020(01)85248-0

  日期：1994.1

  Enolised α-thiocyanato-β-dicarbonyl compounds dimerise in ethanol at room temperature to give tautomeric 4,5-disubstituted 2-amino- and 2-acetamido-thiazoles by a C-S-C + C-N cyclisation. Tautomerism is due to the unusual 4-(β-dicarbonyl-α-thio) substituent. Competing intramolecular cyclisations lead to minor amounts of heterocycles containing the thiazole and/or oxathiole ring systems

  烯化的α-硫氰酸根合-β-二羰基化合物在室温下在乙醇中二聚，通过CSC + CN环化反应生成互变异构体4,5-二取代的2-氨基-和2-乙酰氨基-噻唑。互变异构是由于不寻常的4-（β-二羰基-α-硫代）取代基。竞争性的分子内环化反应会导致少量的含有噻唑和/或草硫醇环系统的杂环
• A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate
  作者：H.M. Meshram、Pramod B. Thakur、B. Madhu Babu、Vikas M. Bangade

  DOI：10.1016/j.tetlet.2012.01.113

  日期：2012.4

  A very rapid, convenient, and general method for the synthesis of alpha-oxo thiocyanates has been described by using clay supported ammonium thiocyanate. The procedure avoids the use of additional catalyst, solvent, aqueous work-up and the yields are high. Moreover, the method is applicable for a variety of aryl, heteroaryl, alkyl alpha-halo carbonyls, beta-keto tosylates, alpha-halo beta-dicarbonyl, alpha-tosyl, beta-dicarbonyl, alkyl halide, and alkyl tosylates. (C) 2012 Elsevier Ltd. All rights reserved.