2,2-bis(ethylthio)acetyl chloride | 39098-91-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2,2-bis(ethylthio)acetyl chloride
• 英文别名: bis-ethylsulfenylacetyl chloride；2,2-diethylthioacetyl chloride；dithioethylacetyl chloride；bis-ethylsulfanyl-acetyl chloride；2,2-Bis(ethylsulfanyl)acetyl chloride
• CAS: 39098-91-4
• 化学式: C₆H₁₁ClOS₂
• 分子量: 198.738
• InChiKey: LVBKAMBKUDQPKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-bis(ethylthio)acetyl chloride 在 吡啶 、 TEA 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 (E)-3-Amino-2-(2,2-bis-ethylsulfanyl-acetylamino)-3-methylsulfanyl-acrylic acid ethyl ester
  参考文献：
  名称：

  Imidazole-based ligands of the Src SH2 protein

  摘要：

  Starting from known Src SH2 inhibitors incorporating five-membered heterocycles or benzamide scaffolds, we prepared tetra substituted imidazole compounds able to interact with the pY, pY + 1 and pY + 3 binding sites of the Src SH2 protein. The synthesis and biological data are presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00138-5
• 作为产物：
  描述：

  glyoxylic acid methyl ester diethyl mercaptal 在 草酰氯 、 水 、 potassium hydroxide 作用下， 反应 14.0h， 生成 2,2-bis(ethylthio)acetyl chloride
  参考文献：
  名称：

  [EN] PROTEASOME INHIBITING ß-LACTAM PRODRUGS USEFUL FOR THE TREATMENT OF CANCER AND NEURODEGENERATIVE DISORDERS
  [FR] PROMÉDICAMENTS À BASE DE SS-LACTAME INHIBITEURS DU PROTÉASOME UTILES POUR LE TRAITEMENT DU CANCER ET DE TROUBLES NEURODÉGÉNÉRATIFS

  摘要：

  本发明通常涉及抑制蛋白酶体的β-内酰胺化合物，用于治疗癌症和神经退行性疾病。该发明还提供了所述化合物的药物组合物和延长释放配方，以及利用所述化合物和/或药物组合物治疗癌症和神经退行性疾病的医疗用途。

  公开号：

  WO2018115497A1

文献信息

• Incorporation of Sulfur Dioxide into the Products of Reaction ofSchiff Bases with Halo- or Alkylthio-ketenes in Liquid SO2. Preliminary communication
  作者：Daniel Bellu?

  DOI：10.1002/hlca.19750580832

  日期：1975.11.5

  A simple ‘three-component-reaction’ between halo- or alkylthio-ketenes, Schiff bases and sulfur dioxide, yielding 4-oxo-1,3-thiazolidine-1,1-dioxides 4 in one step, is presented.

  本文介绍了卤代或烷硫基乙烯酮，席夫碱和二氧化硫之间的简单“三组分反应”，可一步生成4-氧代-1,3-噻唑烷-1,1-二氧化物4。
• A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity
  作者：François Munyemana、Isabelle George、Alain Devos、Alain Colens、Eduard Badarau、Anne-Marie Frisque-Hesbain、Aurore Loudet、Edmond Differding、Jean-Marie Damien、Jeanine Rémion、Jacqueline Van Uytbergen、Léon Ghosez

  DOI：10.1016/j.tet.2015.11.060

  日期：2016.1

  transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms

  由相应的异丁酰胺容易制备的α-氯胺，溴胺和碘烯胺已被发现是将多种醇或羧酸转化为相应卤化物的极佳试剂。产率高并且条件非常温和，因此允许存在敏感的官能团。试剂易于调节，因此可以选择性地对多羟基化分子进行单卤代反应。研究了反应的范围和化学选择性，并提出了反应机理。
• Tandem Pummerer/Mannich Cyclization Cascade of α-Sulfinylamides as a Method To Prepare Aza-Heterocycles
  作者：Albert Padwa、Todd M. Heidelbaugh、Jeffrey T. Kuethe、Michael S. McClure、Qiu Wang

  DOI：10.1021/jo020083x

  日期：2002.8.1

  particularly suited for the assembly of natural product scaffolds. Some preliminary studies were directed toward both mesembrine and deethylibophyllidine. When the model Z-enamido sulfoxide 33 was heated with p-TsOH, a 80% yield of tosylate 34 was obtained as a single diastereomer. In this case, the carbocation intermediate derived from cyclization onto the terminal pi-bond was trapped with p-TsOH from the least

  通过伯胺与酮的缩合，然后使所得的亚胺与乙基亚磺酰基乙酰氯反应，然后用高碘酸钠氧化，可以方便地制备一系列α-亚磺酰胺基。当用p-TsOH处理时，通过涉及初始Pummerer反应，随后将所得N-酰基亚胺离子随后环化到束缚的芳族环上的机理发生环化以产生稠合的异喹啉内酰胺。根据Nazarov型4pi-电环反应，然后将pi环化到N-酰基亚胺离子受阻最小的一侧，合理化了单个非对映异构体的分离。用于产生α-酰基硫鎓离子中间体的另一种方法涉及双（乙基亚硫酰基乙酰基）乙酰胺与四氟硼酸二甲基（甲基）硫代on（DMTSF）的反应。用DMTSF处理数种双-乙基亚磺酰胺通过相关方法以高收率递送了新颖的螺-杂环作为单一非对映异构体。与该级联序列相关的收敛性和立体化学控制使其特别适合于天然产物支架的组装。一些初步的研究针对了甲基安息香和去甲异叶核苷。当将模型Z-en氨基亚砜33与对-TsOH一起加热时，作为单一非对映异
• Proteasome inhibiting β-lactam prodrugs useful for the treatment of cancer and neurodegenerative disorders
  申请人：Vita Api

  公开号：US11053249B2

  公开（公告）日：2021-07-06

  The present invention relates generally to proteasome inhibiting β-lactam compounds useful for the treatment of cancer and neurodegenerative disorders. The invention also provides pharmaceutical compositions and extended release formulations of said compounds, and medical uses of said compounds and/or pharmaceutical compositions to treat cancer and neurodegenerative disorders.

  本发明一般涉及用于治疗癌症和神经退行性疾病的蛋白酶体抑制β-内酰胺化合物。本发明还提供了所述化合物的药物组合物和缓释制剂，以及所述化合物和/或药物组合物治疗癌症和神经退行性疾病的医学用途。
• Regiochemical and stereochemical studies on halocyclization reactions of unsaturated sulfides
  作者：Xiao-Feng Ren、Edward Turos、Charles H. Lake、Melvyn Rowen Churchill

  DOI：10.1021/jo00125a038

  日期：1995.10

  The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent. Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts. The endo- versus exo-regioselectivity of these alkenyl sulfide ring closures most likely reflects the difference in thermodynamic stabilities of the beta-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate. The efficiency of the cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers. Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides. Conversely the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length. Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring, The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control. The methodology has been applied to the synthesis of unusual bicyclic beta-lactams related to the penicillin family of antibiotics.