allyl(prop-2-yn-1-yl)sulfane | 89027-60-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 烯丙基硫化合物
• 英文名称: allyl(prop-2-yn-1-yl)sulfane
• 英文别名: allyl propargyl sulfide；3-prop-2-ynylsulfanylprop-1-ene
• CAS: 89027-60-1
• 化学式: C₆H₈S
• 分子量: 112.196
• InChiKey: PDTBDBRANSKXPV-UHFFFAOYSA-N

物化性质

• 保留指数：
  858;858

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  allyl(prop-2-yn-1-yl)sulfane 在 偶氮二异丁腈 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (Z)-ajoene
  参考文献：
  名称：

  Ajoene, A Stable Garlic By-Product, Inhibits High Fat Diet-Induced Hepatic Steatosis and Oxidative Injury Through LKB1-Dependent AMPK Activation

  摘要：

  Hepatic steatosis, a hepatic component of metabolic syndrome, is common and may progress to steatohepatitis and cirrhosis. The liver X receptor-alpha (LXR alpha)-sterol regulatory element binding protein-1c (SREBP-1c) pathway plays a key role in hepatic steatosis. This study investigated the potential of ajoene, a stable garlic by-product, to inhibit high fat diet (HFD)-induced hepatic steatosis and the underlying mechanism. Ajoene treatment attenuated fat accumulation and induction of lipogenic genes in the liver of HFD-fed mice. Blood biochemical analyses and histopathologic examinations showed that ajoene prevented liver injury with the inhibition of oxidative stress, as evidenced by thiobarbituric acid reactive substances formation and nitrotyrosinylation. Moreover, ajoene treatment inhibited LXR alpha agonist (T0901317)-mediated SREBP-1c activation, and transactivation of the lipogenic target genes in hepatocytes. Ajoene was found to activate AMP-activated protein kinase (AMPK) via LKB1, responsible for the inhibition of p70 ribosomal S6 kinase-1 (S6K1). The ability of ajoene to repress T0901317-induced SREBP-1c expression was antagonized by inhibition of AMPK or activation of S6K1, supporting the role of these kinases in the antisteatotic effect. Our results demonstrate that ajoene has an effect of activating AMPK through LKB1 and inhibit S6K1 activity, contributing to the prevention of SREBP-1c-mediated hepatic lipogenesis via the inhibition of LXR alpha activity. Antioxid Redox Signal. 14, 187-202.

  DOI：

  10.1089/ars.2010.3190
• 作为产物：
  描述：

  烯丙硫醇 、 3-溴丙炔 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 、 甲苯 为溶剂， 反应 0.5h， 以25%的产率得到allyl(prop-2-yn-1-yl)sulfane
  参考文献：
  名称：

  Aryne引发烯丙基和炔丙基硫醚的[2,3]-σ重排

  摘要：

  报道了烯丙基和炔丙基硫醚的[2,3]-σ重排的有效方案。关键的叶立德intermediate中间体是通过芳烃的S-芳基化原位形成的。这种无过渡金属的方法可以方便地以良好至极好的收率获得各种官能化的硫醚衍生物。

  DOI：

  10.1039/c7ob00914c

文献信息

• Gold-Catalyzed Oxidative Hydrative Alkenylations of Propargyl Aryl Thioethers with Quinoline <i>N</i>-Oxides Involving a 1,3-Sulfur Migration
  作者：Sachin Bhausaheb Wagh、Rahulkumar Rajmani Singh、Rajkumar Lalji Sahani、Rai-Shung Liu

  DOI：10.1021/acs.orglett.9b00705

  日期：2019.4.19

  This work reports gold-catalyzed oxidative alkenylations of quinoline N-oxides with propargyl aryl thioethers to afford 3-hydroxy-1-alkylidenephenylthiopropan-2-one via a 1,3-sulfur group migration. The mechanism of this reaction is postulated to involve an α-oxo gold carbene intermediate followed by formation of a four-membered sulfonium ring that is ring-opened by one H2O to form a gold enolate. A

  这项工作报道了喹啉N-氧化物与炔丙基芳基硫醚的金催化氧化烯基化反应，通过1，3-硫基团迁移得到3-羟基-1-亚烷基苯硫基丙烷-2-酮。推测该反应的机理包括：α-氧代金卡宾中间体，然后形成四元ring环，该环被一个H 2 O开环形成烯醇金。该烯醇化物与第二种喹啉N-氧化物的最终缩合产生烯基化产物，并伴有1,3-硫的移位。
• Silver-catalysed Doyle–Kirmse reaction of allyl and propargyl sulfides
  作者：Paul W. Davies、Sébastien J.-C. Albrecht、Giulio Assanelli

  DOI：10.1039/b822584b

  日期：——

  The silver-catalysed Doyle–Kirmse reaction of propargyl and allyl sulfides with diazo compounds is disclosed. The carbon–carbon bond forming process proceeds with a range of substituents and functionality under mild conditions.

  公开了炔丙基和烯丙基硫与重氮化合物的银催化的Doyle-Kirmse反应。碳-碳键的形成过程在温和条件下会进行一系列取代基和官能化反应。
• Synthesis of functionalized CF3-containing heterocycles via [2,3]-sigmatropic rearrangement and sequential catalytic carbocyclization
  作者：Daria V. Vorobyeva、Artur K. Mailyan、Alexander S. Peregudov、Natalia M. Karimova、Tamara P. Vasilyeva、Ivan S. Bushmarinov、Christian Bruneau、Pierre H. Dixneuf、Sergey N. Osipov

  DOI：10.1016/j.tet.2011.03.031

  日期：2011.5

  CF3-substituted and nitrogen or sulfur-containing heterocycles has been developed directly from diazocompounds CF3C(N2)Z (Z=CO2Me, P(O)(OEt)2). The method is based on the direct selective synthesis of doubly unsaturated substrates followed by metal-mediated carbocylization. The first step has been performed by Cu(II)-catalyzed [2,3]-sigmatropic rearrangement of propargyl- or/and allyl-containing sulfur

  直接从重氮化合物CF 3 C（N 2）Z（Z = CO 2 Me，P（O）（OEt）2）直接开发了一种新的有效接触官能化CF 3取代的含氮或含硫的杂环的方法。该方法基于双不饱和底物的直接选择性合成，然后进行金属介导的碳环化。第一步是通过Cu（II）催化的炔丙基或/和烯丙基的硫和氮的炔丙基的[2,3]σ重排导致氟化烯炔，二烯烃，尤其是烯炔衍生物。第二步涉及通过闭环复分解和Pauson-Khand反应进行碳环化。
• Alkynes as masked ylides: Gold-catalysed intermolecular reactions of propargylic carboxylates with sulfides
  作者：Paul W. Davies、Sébastien J.-C. Albrecht

  DOI：10.1039/b714813e

  日期：——

  The in situ-generation of sulfur ylides by the gold-catalysed rearrangement of propargylic carboxylates in the presence of sulfides has resulted in highly efficient and novel transformations.

  在硫化物存在的情况下，通过金催化丙炔基羧酸酯的重排，原位生成硫酰化物，从而实现了高效、新颖的转化。
• Multigram Synthesis of Heterabicyclo[n.1.0]alkan‐1‐yl Trifluoroborates
  作者：Ihor Kleban、Yevhen Krokhmaliuk、Sofiia Reut、Serhii Shuvakin、Vyacheslav V. Pendyukh、Oleksandr I. Khyzhan、Dmytro S. Yarmoliuk、Andriy V. Tymtsunik、Yuliya V. Rassukana、Oleksandr O. Grygorenko

  DOI：10.1002/ejoc.202000977

  日期：2021.12.21

  Multigram synthesis of oxa‐ and azabicyclo[n.1.0]alkan‐1‐yl trifluoroborates relying on efficient 4–5‐step reaction sequences is described. The title compounds was obtained in up to 50 g scale in a single run (10–41 % overall yield).

  本文描述了依赖于有效的4-5步反应序列的oxa-和氮杂双环[ n .1.0]烷烃-1-基三氟硼酸酯的合成方法。一次即可获得高达50 g的标题化合物（总收率10–41％）。