3-methyl-(5S)-thiotetronic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 3-methyl-(5S)-thiotetronic acid
• 英文别名: (5S,1'E)-2,5-Dihydro-3,5-dimethyl-4-hydroxy-5-prop-1'-enyl-2-oxothiophene；(S,E)-4-hydroxy-3,5-dimethyl-5-(prop-1-enyl)thiophen-2(5H)-one；(5S)-4-hydroxy-3,5-dimethyl-5-[(E)-prop-1-enyl]thiophen-2-one
• 化学式: C₉H₁₂O₂S
• 分子量: 184.259
• InChiKey: AIYZYVOEVDBZRS-MOVJSRMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  O-(2S,3E)-4-Ethoxycarbonylpent-3-en-2-yl S-methyldithiocarbonate 在 氢氧化钾 、 lithium cyclohexylisopropylamide 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 15.0~145.0 ℃ 、53.33 Pa 条件下， 反应 0.75h， 生成 3-methyl-(5S)-thiotetronic acid
  参考文献：
  名称：

  使用手性转移通过黄原酸烯丙酯至二硫代碳酸酯的重排进行硫代反酸的不对称合成。（5 R）-2,5-二氢-4-羟基-5-甲基-3-苯基-5-丙-1'-烯基-2-氧代噻吩的X射线晶体结构

  摘要：

  已经开发了基于黄原酸烯丙基酯至二硫代碳酸酯重排的硫代反酸的不对称合成，通过X射线晶体结构测定证实了产物的绝对构型。

  DOI：

  10.1039/c39870001228

文献信息

• Synthesis and biological activity of enantiomeric pairs of 5-vinylthiolactomycin congeners
  作者：Kohei Ohata、Shiro Terashima

  DOI：10.1016/j.bmcl.2007.04.067

  日期：2007.7

  prepared, it appeared evident that in vitro antibacterial and mammalian type I FAS inhibitory activity of thiolactomycin congeners can be cleanly separated by changing not only the structure but also the absolute configuration of the side chain at the C(5)-position. These studies led us to explore (S)-3-demethyl-5-(pent-1-enyl)thiolactomycin derivative [(S)-4-hydroxy-5-methyl-5-(pent-1-enyl)-5H-thiophen-2-one]

  通过使用我们先前探索的用于合成硫菌丝霉素及其3-脱甲基衍生物的对映体对的有效合成路线，合成了十二个5-乙烯基硫基乳酸霉素同系物的对映体对。从使用获得的同源物以及先前制备的对映体对的硫菌霉素及其3-脱甲基衍生物进行的生物活性分析，似乎可以看出，通过不改变不仅是侧链在C（5）位置的结构而且是绝对构型。
• An asymmetric synthesis of thiotetronic acids using chirality transfer via an allyl xanthate-to-dithiocarbonate rearrangement. X-Ray crystal structure of (5R)-2,5-dihydro-4-hydroxy-5-methyl-3-phenyl-5-prop-1′-enyl-2-oxothiophene
  作者：Mark S. Chambers、Eric J. Thomas、David J. Williams

  DOI：10.1039/c39870001228

  日期：——

  An asymmetric synthesis of thiotetronic acids has been developed which is based upon an allyl xanthate-to-dithiocarbonate rearrangement, the absolute configuration of the products being confirmed by an X-ray crystal structure determination.

  已经开发了基于黄原酸烯丙基酯至二硫代碳酸酯重排的硫代反酸的不对称合成，通过X射线晶体结构测定证实了产物的绝对构型。
• Synthesis and Biological Activity of Enantiomeric Pairs of 5-(Alk-2-enyl)thiolactomycin and 5-[(E)-Cycloalk-2-enylidenemethyl]thiolactomycin Congeners
  作者：Kohei Ohata、Shiro Terashima

  DOI：10.1248/cpb.57.920

  日期：——

  The title compounds were synthesized by the efficient route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. These studies were carried out to prove the flexibility of the previously explored synthetic route to natural thiolactomycin (TLM) 1 and to examine the structure–activity relationship on the 5-position of 1. While all of the synthesized congeners lacked in vitro antibacterial activity, these studies led us to find 5-(alk-2-enyl)-TLM (ent-4d) which exhibits mammalian type I fatty acid synthase (FAS) inhibitory activity equal to that of C75, a potent inhibitor reported previously. It was also found that 5-[(E)-cycloalk-2-enylidenemethyl]-TLM (ent-5c) exhibited slightly less potent mammalian type I FAS inhibitory activity than C75.

  标题化合物是通过之前探索的合成硫代霉素对映体及其 3-去甲基衍生物的高效路线合成的。虽然所有合成的同系物都缺乏体外抗菌活性，但这些研究使我们发现了 5-(alk-2-enyl)-TLM（ent-4d），它对哺乳动物 I 型脂肪酸合成酶（FAS）的抑制活性与之前报道的强效抑制剂 C75 相当。研究还发现，5-[(E)-环烷-2-亚烯基甲基]-TLM（ent-5c）对哺乳动物 I 型脂肪酸合成酶的抑制活性略低于 C75。
• Chambers, Mark S.; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1997, # 4, p. 417 - 431
  作者：Chambers, Mark S.、Thomas, Eric J.

  DOI：——

  日期：——