4-mercapto-6-methyl-pyran-2-one | 58035-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-mercapto-6-methyl-pyran-2-one
• 英文别名: 4-mercapto-6-methylpyran-2-one；4-mercapto-6-methyl-2H-pyran-2-one；2H-Pyran-2-one, 4-mercapto-6-methyl-；6-methyl-4-sulfanylpyran-2-one
• CAS: 58035-29-3
• 化学式: C₆H₆O₂S
• 分子量: 142.178
• InChiKey: KELWGMKIOSOXEM-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C
• 沸点：
  234.3±40.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-mercapto-6-methyl-pyran-2-one 在 sodium hydroxide 、 苄基三乙基氯化铵 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 水 为溶剂， 反应 6.5h， 生成 3-[2-(2,4-Dichlorophenoxy)acetyl]-6-methylthieno[3,2-c]pyran-4-one
  参考文献：
  名称：

  Studies on triacetic acid lactone-annulated heterocycles: synthesis of 3-aryloxyacetyl-6-methyl-2,3-dihydrothieno[3,2- c ]pyran-4-ones by tandem cyclization

  摘要：

  The hitherto unreported 3-aryloxyacetyl-6-methyl-2,3-dihydrothieno[3,2-c]pyran-4-ones were synthesized in 62-71% yield by the sulfoxide rearrangement of 4-(4'-aryloxybut-2'-ynylthio)-6-methyl-2-pyrone. The substrates were synthesized by phase-transfer-catalysed alkylation of the hitherto unreported 4-mercapto-6-methylpyran-2-one. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01418-7
• 作为产物：
  描述：

  6-methyl-4-tosyloxy-2(2H)-pyranone 在 sodium hydrogen sulfide 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 4-mercapto-6-methyl-pyran-2-one
  参考文献：
  名称：

  作为潜在 HIV-1 逆转录酶抑制剂的新型 2H-Pyran-2-one 衍生物的设计、合成和生物学评价

  摘要：

  为了寻找更有效的抗 HIV 感染药物，作为非核苷逆转录酶抑制剂 (NNRTIs)，一系列具有基于天然产物 (+)-calanolide A 和合成分子 α-APA 的混合结构的新分子，称为通过对接计算选择了这种酶的有效和选择性抑制剂。聚合合成策略得到了 21 种具有 2H-吡喃-2-one 结构单元并带有等排修饰的化合物，这些化合物在 HIV 感染的 CEM 细胞培养物中进行了测试。只有化合物 6 (4-((2-(1H-indol-3-yl)ethyl)amino)-6-methyl-2H-pyran-2-one) 显示出抑制活性 (EC50: 25-50 µM)。然而，它与对人 T 淋巴细胞 (CEM) 细胞培养物的相对较高的细胞抑制作用有关，无论是化学结构还是计算方法，都不容易预测。

  DOI：

  10.1002/ardp.201400235

文献信息

• Studies in Thio‐Claisen Rearrangement: Regioselective Synthesis of Thiopyrano[2,3‐<i>b</i>]pyran‐2‐ones and Thieno[2,3‐<i>b</i>]pyran‐2‐ones
  作者：K. C. Majumdar、S. Sarkar、S. Ghosh

  DOI：10.1081/scc-120030314

  日期：2004.12.31

  4‐Mercapto‐6‐methyl‐2‐pyrone was alkylated with different allylic and propargylic halides under phase transfer catalyzed condition in the presence of TBAB or BTEAC catalyst in chloroform–aqueous NaOH (1%) at room temperature. The S‐alkylated thiopyran‐2‐ones were then refluxed in quinoline or in chlorobenzene to give 4‐chloromethylthiopyrano[2,3‐b]pyran‐2‐one and 4‐hydroxymethylthiopyrano[2,3‐b]pyran‐2‐one or several

  摘要 4-Mercapto-6-methyl-2-pyrone 在相转移催化条件下，在 TBAB 或 BTEAC 催化剂存在下，在氯仿 - NaOH 水溶液 (1%) 中，在室温下用不同的烯丙基和炔丙基卤化物烷基化。S-烷基化噻喃-2-酮然后在喹啉或氯苯中回流，得到4-氯甲基噻喃[2,3-b]吡喃-2-酮和4-羟基甲基吡喃并[2,3-b]吡喃-2-酮或几个噻吩并[2,3-b]吡喃-2-酮。
• Cephalosporin derivatives and pharmaceutical compositions
  申请人：Beecham Group p.l.c.

  公开号：US05158946A1

  公开（公告）日：1992-10-27

  .beta.-Lactam compounds of the formula (I) including pharmaceutically acceptable salts and in vivo hydrolysable esters, processes for their preparation and their use as antibiotics: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido; R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin; R.sup.3 is hydrogen or a readily removable carboxy protecting group (such as a pharmaceutically acceptable in-vivo hydrolysable ester group); R.sup.4 is a .gamma.- or .delta.-lactone ring optionally containing one or (where applicable) two endocyclic double bonds, which ring is optionally substituted at any carbon atom by alkyl, dialkylamino, alkoxy, hydroxy, halogen or aryl, which in the case of more than one substituent may be the same or different, or is optionally di-substituted at two adjacent carbon atoms, which are available for substitution, to form an aromatic fused bicyclic system; x and y are independently 0 or 1; X is S, SO, SO.sub.2, O or CH.sub.2 ; and Y is O or S.

  .beta.-内酰胺化合物的公式（I），包括药学上可接受的盐和体内可水解的酯，其制备过程以及作为抗生素的用途：其中R.sup.1是氢，甲氧基或甲酰基；R.sup.2是酰基，特别是抗菌活性头孢菌素的酰基；R.sup.3是氢或容易去除的羧基保护基（例如，药学上可接受的体内水解酯基）；R.sup.4是.γ.-或.δ.-内酯环，可选地含有一个或（如适用）两个内环双键，该环在任何碳原子上可选择性地被烷基，二烷基氨基，烷氧基，羟基，卤素或芳基取代，如果有多个取代基，则可以相同或不同，或可选择性地在两个相邻的碳原子上进行双取代，以形成一个芳香融合的双环系统；x和y独立地为0或1；X为S，SO，SO.sub.2，O或CH.sub.2；Y为O或S。
• Regioselective Synthesis of Pyrone-Annulated Sulfur Heterocycles by Aryl Radical Cyclization
  作者：K. Majumdar、S. Muhuri

  DOI：10.1055/s-2006-942499

  日期：2006.8

  The tri-n-butyltin hydride mediated cyclization of a number of 4-(2′-bromophenoxymethyl)-7-methylthiopyrano[3,2-c]pyran-5-ones have been carried out to afford tetracyclic [6,6]pyranothiopyrans in 70-80% yield and good to excellent diastereoselectivity. The substrate ethers were obtained by a thio-Claisen rearrangement of the corresponding 4-(4′-aryloxybut-2′-ynyl)-6-methyl pyran-2-ones. The cis stereochemistry of the predominant diastereomer has been corroborated by single crystal X-ray analysis.

  在三正丁基氢化锡介导下，对一些 4-(2′-溴苯氧甲基)-7-甲硫基吡喃并[3,2-c]吡喃-5-酮进行了环化反应，得到了四环[6,6]吡喃硫烷，产率为 70-80%，非对映选择性良好至极佳。底物醚是通过相应的 4-(4′-芳氧基丁-2′-炔基)-6-甲基吡喃-2-酮的硫代-克莱森重排反应得到的。单晶 X 射线分析证实了主要非对映异构体的顺式立体化学性质。
• Cephalosporinderivatives, process for their preparation and pharmaceutical compositions
  申请人：BEECHAM GROUP PLC

  公开号：EP0418020A2

  公开（公告）日：1991-03-20

  β-Lactam compounds of the formula (I) including pharmaceutically acceptable salts and in vivo hydrolysable esters, processes for their preparation and their use as antibiotics: wherein R1 is hydrogen, methoxy or formamido; R2 is an acyl group, in particular that of an antibacterially active cephalosporin; R3 is hydrogen or a readily removable carboxy protecting group (such as a pharmaceutically acceptable in-vivo hydrolysable ester group); R4 is a y- or δ-lactone,ring optionally containing one or (where applicable) two endocyclic double bonds, which ring is optionally substituted at any carbon atom by alkyl, dialkylamino, alkoxy, hydroxy, halogen or aryl, which in the case of more than one substituent may be the same or different, or is optionally di-substituted at two adjacent carbon atoms, which are available for substitution, to form an aromatic fused bicyclic system; x and y are independently 0 or 1; x is S, SO, S02, 0 or CH2; and Y is 0 or S.

  式 (I) 的 β-内酰胺化合物，包括药学上可接受的盐类和体内可水解的酯类，其制备工艺及其作为抗生素的用途： 其中 R1 是氢、甲氧基或甲酰胺基； R2 是酰基，特别是抗菌活性头孢菌素的酰基； R3 是氢或易于去除的羧基保护基团（如药学上可接受的体内可水解酯基）； R4是y-或δ-内酯环，可选择含有一个或（适用时）两个内环双键，该环可选择在任何碳原子上被烷基、二烷基氨基、烷氧基、羟基、卤素或芳基取代，在多个取代基相同或不同的情况下，也可选择在两个相邻碳原子上被二取代，这两个碳原子可用于取代，以形成芳香族融合双环体系；x 和 y 独立地为 0 或 1；x 为 S、SO、S02、0 或 CH2；Y 为 0 或 S。
• Regioselective synthesis of heterocycles by sigmatropic rearrangement: passage to 3,11a-dimethyl-6a,11a-dihydro-1H,6H-pyrano[3′,4′:5,6]thiopyrano[4,3-b][1]benzofuran-1-one
  作者：Krishna C. Majumdar、Uday K. Kundu、Subhojit Ghosh

  DOI：10.1039/b206287a

  日期：——