but-1-yn-4-yl thioacetate | 86220-08-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: but-1-yn-4-yl thioacetate
• 英文别名: but-1-yn-4-yl thiolacetate；thioacetic acid S-but-3-ynyl ester；(S)-but-3-ynyl ethanethioate；3-butynyl ethanethioate；S-(but-3-yn-1-yl) ethanethioate；S-but-3-ynyl ethanethioate
• CAS: 86220-08-8
• 化学式: C₆H₈OS
• 分子量: 128.195
• InChiKey: ZVMVPZWXIWUFSN-UHFFFAOYSA-N

物化性质

• 沸点：
  76-78 °C(Press: 30 Torr)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  but-1-yn-4-yl thioacetate 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 丁-3-炔-1-硫醇
  参考文献：
  名称：

  为优化升的无论是碳青霉烯类抗生素灭活的合成途径，d-转LDT MT1的结核分枝杆菌和稳定性朝向水解β内酰胺酶无刷交流

  摘要：

  目前正在评估碳青霉烯类的β-内酰胺（如美罗培南）与β-内酰胺酶抑制剂克拉维酸盐的组合，以治疗耐药性结核病。然而，从未批准用于人类的碳青霉烯类药物能够优化灭活结核分枝杆菌的非常规β-内酰胺靶标或用于避免广谱β-内酰胺酶BlaC水解。在这里，我们报告了由β-内酰胺和碳青霉烯核心的五元环修饰的两条侧链修饰的三种合成途径。特别是，我们表明，铜（I）催化的叠氮化物-炔烃休斯根环加成反应是与碳青霉烯类的高度不稳定的β内酰胺环，并且通过该反应生成的三唑环被很好的耐受性的失活完全兼容升，d-转肽酶Ldt Mt1靶标。就Ldt Mt1的体外灭活效率和BlaC减少的水解效率而言，我们的几种新型碳青霉烯均优于美罗培南。

  DOI：

  10.1021/acs.jmedchem.6b00096
• 作为产物：
  描述：

  4-溴-1-丁炔 、 potassium thioacetate 以 乙腈 为溶剂， 反应 20.0h， 生成 but-1-yn-4-yl thioacetate
  参考文献：
  名称：

  Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags

  摘要：

  The design, synthesis, and both experimental and theoretical studies of several novel 9-(acylimino)- and 9-(sulfonylimino)pyronin derivatives containing either an oxygen or a silicon atom at position 10 are reported. These compounds, especially the Si analogues, exhibit remarkably large Stokes shifts (around 200 nm) while still possessing a high fluorophore brightness, absorption bands in the near-UV and visible part of the spectrum, and high thermal and photochemical stabilities in protic solvents. The reason for the observed large Stokes shifts is an intramolecular charge-transfer excitation of an electron from the HOMO to the LUMO of the chromophore, accompanied by elongation of the C9-N bond and considerable solvent reorganization due to hydrogen bonding to the solvent. Due to the photophysical properties of the studied compounds and their facile and high-yielding synthesis, as well as a simple protocol for their bioorthogonal ligation to a model saccharide using a Huisgen alkyne-azide cycloaddition, they represent excellent candidates for biochemical and biological applications as fluorescent tags and indicators for multichannel imaging. 9-(Acylimino)pyronins alter their optical properties upon protonation and may also be used as pH sensors.

  DOI：

  10.1021/jo502213t

文献信息

• N-(HETERO)ARYL-PYRROLIDINE DERIVATIVES OF PYRAZOL-4-YL-PYRROLO[2,3-d]PYRIMIDINES AND PYRROL-3-YL-PYRROLO[2,3-d]PYRIMIDINES AS JANUS KINASE INHIBITORS
  申请人：Rodgers James D.

  公开号：US20100298334A1

  公开（公告）日：2010-11-25

  The present invention relates to N-(hetero)aryl-pyrrolidine derivatives of Formula I: which are JAK inhibitors, such as selective JAK1 inhibitors, useful in the treatment of JAK-associated diseases including, for example, inflammatory and autoimmune disorders, as well as cancer.

  本发明涉及式I的N-(杂)芳基吡咯烷衍生物： 这些是JAK抑制剂，如选择性JAK1抑制剂，在治疗JAK相关疾病方面具有用处，例如炎症和自身免疫性疾病，以及癌症。
• The use of a [4 + 2] cycloaddition reaction for the preparation of a series of ‘tethered’ Ru(<scp>ii</scp>)–diamine and aminoalcohol complexes
  作者：Fung Kei Cheung、Aidan M. Hayes、David J. Morris、Martin Wills

  DOI：10.1039/b700744b

  日期：——

  A series of catalysts have been prepared for use in the asymmetric transfer hydrogenation of ketones. The complexes were prepared using a [4 + 2] cycloaddition reaction at a key step in the reaction sequence. This provides a means for the synthesis of catalysts with modifications at specific sites.

  已经制备了一系列用于酮的不对称转移氢化的催化剂。使用[4 + 2]环加成反应在反应顺序的关键步骤制备配合物。这提供了在特定位点进行修饰的合成催化剂的方法。
• Gold- or Platinum-Catalyzed Synthesis of Sulfur Heterocycles: Access to Sulfur Ylides without Using Sacrificial Functionality
  作者：Paul W. Davies、Sébastien J.-C. Albrecht

  DOI：10.1002/anie.200904309

  日期：2009.10.19

  It′s no sacrifice: Alkynes have been used as direct precursors to sulfur ylides under gold or platinum π‐acid catalysis in an atom‐economic manner. An intramolecular redox reaction between an alkyne group with a tethered sulfoxide unit generates a sulfur ylide, which undergoes 2,3‐sigmatropic rearrangement. Acyclic substrates are cycloisomerized to afford functionalized dihydrothiophenones (see scheme)

  这不是什么牺牲：炔烃已经以原子经济的方式用作金或铂π-酸催化下硫代叶立德的直接前体。炔基与束缚的亚砜单元之间的分子内氧化还原反应产生了硫内鎓盐，其经历了2,3-σ重排。将无环底物进行环异构化以提供官能化的二氢噻吩酮（参见方案）和二氢硫吡喃酮。
• Facile synthesis of dihaloheterocycles via electrophilic iodocyclization
  作者：Fan Yang、Tienan Jin、Ming Bao、Yoshinori Yamamoto

  DOI：10.1016/j.tet.2011.08.084

  日期：2011.12

  An efficient and facile electrophilic iodocyclization for the synthesis of various O-, N-, and S-containing dihaloheterocycles has been developed. A wide range of the substituted propargyl alcohols having –OH, –NTs, and –SAc functional groups reacted with molecular iodine or bromoiodine at ambient temperature to produce the corresponding dihalogenated O-, N-, and S-containing five- and six-membered

  已经开发了用于合成各种含O-，N-和S-的二卤代杂环的有效且容易的亲电碘代环化反应。在环境温度下，具有–OH，–NTs和–SAc官能团的广泛取代的炔丙醇与分子碘或溴碘反应生成相应的二卤代O-，N-和S-含有高至高收率的五元和六元杂环；在优化的溶剂条件下，各种在C4位带有–OH，–NTs和–SAc官能团的取代的丁-2-yn-1-one与环境温度下的碘或溴碘反应，得到相应的3,4-二碘和3-溴-4-碘取代的呋喃，吡咯和噻吩，产量高至高。已经研究了将所得的含碘或溴的产物进一步转化为可能用作有机材料中间体的聚芳族化合物。
• Attempts at vinyl radical carbonylation through cyclization onto carbonyl and cyano groups
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia、Piero Spagnolo

  DOI：10.1016/s0040-4020(98)00458-x

  日期：1998.7

  Sulfanylvinyl radicals 4–6, 16, produced from toluenesulfanyl radical addition to alkynes 1–3, 15, gave only products arising from cyclization onto the thiophenyl ring and H-abstraction. No products were obtained deriving from possible 5-membered cyclization onto the esteric or thioesteric carbonyl group. Similar results were obtained from toluenesulfanyl radical addition to alkynyl nitriles 20 and

  Sulfanylvinyl基团4-6，16，从toluenesulfanyl基加至炔烃制备1-3，15，给从环化而产生到噻吩环和H-抽象仅产品。没有得到从可能的五元环化到酯或硫代酯羰基上的产物。从甲苯硫烷基到炔基腈20和24的加成反应也得到了相似的结果，但没有提供任何证据表明5或6元乙烯基自由基环合到脂肪族氰基上。相反，甲苯硫基-和苯硫基-乙烯基基团32和37a均平滑地环化到芳族氰基上，从而生成酮35和39。该协议代表了一种新型的间接自由基羰基化，并提供了一种有用的合成茚满的方法。