methyl 5-mercaptopentanoate | 83009-94-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 5-mercaptopentanoate
• 英文别名: Methyl 5-sulfanylpentanoate
• CAS: 83009-94-3
• 化学式: C₆H₁₂O₂S
• 分子量: 148.226
• InChiKey: QPUJGZBRSXYOTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 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：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-mercaptopentanoate 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5-(3-phenylprop-2-enyl)pentanoic acid
  参考文献：
  名称：

  铑类胡萝卜素介导的环化。第5部分。6和7元硫杂环的环状sulph化物的合成和重排

  摘要：

  用乙酸铑（II）处理重氮硫醇，得到六元和七元硫杂环。重氮硫化物可生成环状sulph，它们可分离或重排，具体取决于硫上取代基的性质。

  DOI：

  10.1016/s0040-4020(01)96017-x
• 作为产物：
  描述：

  5-溴戊酸甲酯 在 硫酸 、 硫脲 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 methyl 5-mercaptopentanoate
  参考文献：
  名称：

  Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

  摘要：

  In vivo imaging of regional fatty acid oxidation (FAO) rates would have considerable potential for evaluation of mammalian diseases. We have synthesized and evaluated F-18-labeled thia fatty acid analogues as metabolically trapped FAO probes to understand the effect of chain length, degree of unsaturation, and placement of the thia substituent on myocardial uptake and retention. 18-[F-18]Fluoro-4-thia-(9Z)-octadec-9-enoic acid (3) showed excellent heart/background radioactivity concentration ratios along with highest retention in heart and liver. Pretreatment of rats with the CPT-1 inhibitor, POCA, caused >80% reduction in myocardial uptake of 16-[F-18]fluoro-4-thiahexadecanoic acid (2) and 3, indicating high specificity for FAO. In contrast, 18-[F-18]fluoro-4-thiaoctadecanoic acid (4) showed dramatically reduced myocardial uptake and blunted response to POCA. 18-[F-18]Fluoro-6-thiaoctadecanoic acid (5) showed moderate myocardial uptake and no sensitivity of myocardial uptake to POCA. The results demonstrate relationships between structures of F-18-labeled thia fatty acid and uptake and their utility as FAO probes in various tissues.

  DOI：

  10.1021/jm301345v

文献信息

• Total Synthesis of (+)-Acanthodoral by the Use of a Pd-Catalyzed Metal-ene Reaction and a Nonreductive 5-<i>e</i><i>xo</i>-Acyl Radical Cyclization
  作者：Liming Zhang、Masato Koreeda

  DOI：10.1021/ol0363063

  日期：2004.2.1

  [reaction: see text] The first total synthesis of the antibiotic acanthodoral (1) has been achieved from 3-methyl-2-cyclohexen-1-one in 19 steps in 2.1% overall yield. The synthesis features the use of a Pd-ene reaction in the presence of CO to form the endocyclic alkene 8, a nonreductive acyl radical cyclization reaction, and a ring contraction reaction by the Wolff rearrangement. (+)-Acanthodoral

  [反应：见正文]抗生素Acanthodoral（1）的第一个全合成反应是由3-甲基-2-环己烯-1-酮分19个步骤完成的，总产率为2.1％。该合成的特征在于在CO存在下使用Pd-烯反应形成环内烯烃8，非还原性酰基自由基环化反应和通过Wolff重排的环收缩反应。还从（+）-S-2，2-二甲基-6-亚甲基环己烷羧酸开始合成了（+）-棘棘醛。
• Synthesis of thiaprostaglandin E1 derivatives.
  作者：ATSUO HAZATO、TOSHIO TANAKA、KENZO WATANABE、KIYOSHI BANNAI、TAKESHI TORU、NORIAKI OKAMURA、KENJI MANABE、AKIRA OHTSU、FUKUYOSHI KAMIMOTO、SEIZI KUROZUMI

  DOI：10.1248/cpb.33.1815

  日期：——

  A series of new thiaprostaglandins, 4-thia-, 5-thia-, 6-thia-and 7-thiaprostaglandin E1 methyl esters (3b, 4b, 5b, and 6b), was synthesized by a three-component coupling process using a chiral common synthon, (R)-4-tert-butyldimethylsilyloxy-2-cyclopentenone (1). Among these thiaprostaglandins, 7-thiaprostaglandin E1 methyl ester showed the most potent platelet aggregationinhibiting activity.

  一系列新型硫代前列腺素，即4-硫代-、5-硫代-、6-硫代-和7-硫代前列腺素E1甲酯（3b、4b、5b和6b），通过使用手性共同合成砌块（R）-4-叔丁基二甲基甲硅烷氧基-2-环戊烯酮（1）的三组分偶联反应合成。在这些硫代前列腺素中，7-硫代前列腺素E1甲酯显示出最强的血小板聚集抑制活性。
• 3-Arylisothiazoles and their use as herbicides
  申请人：——

  公开号：US20040023807A1

  公开（公告）日：2004-02-05

  3-Arylisothiazoles of the formula I 1 in which the variables X, Q, R 1 , R 2 , R 3 , R 4 , R 5 are as defined in claim 1, and salts thereof, and their use for controlling harmful plants, are described.

  描述了具有以下公式I1的3-芳基异噻唑，其中变量X、Q、R1、R2、R3、R4、R5如权利要求1中定义的，并且其盐及其用于控制有害植物的用途。
• 2-Aryl-5-trifluoromethylpyridines
  申请人：——

  公开号：US20040043903A1

  公开（公告）日：2004-03-04

  The present invention relates to 2-aryl-5-trifluoromethylpyridines of the formula I 1 in which the variables m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and X have the meanings given in claim 1, and their agriculturally tolerated salts. Moreover, the invention relates to the use of compounds I and their salts as herbicides and/or for the desiccation and/or defoliation of plants, to herbicidal compositions and compositions for the desiccation and/or defoliation of plants comprising the compounds I and/or their salts as active substances.

  本发明涉及具有以下通式I中给定的变量m、R1、R2、R3、R4、R5、R6和X含义的2-芳基-5-三氟甲基吡啶，以及它们在农业中可容忍的盐。此外，本发明涉及化合物I及其盐作为除草剂和/或用于植物干燥和/或落叶的用途，以及包含化合物I和/或其盐作为活性物质的除草剂组合物和用于植物干燥和/或落叶的组合物。
• Synthesis of 7-thiaprostaglandin E1 congeners: Potent inhibitors of platelet aggregation.
  作者：TOSHIO TANAKA、NORIAKI OKAMURA、KIYOSHI BANNAI、ATSUO HAZATO、SATOSHI SUGIURA、KENJI MANABE、FUKUYOSHI KAMIMOTO、SEIZI KUROZUMI

  DOI：10.1248/cpb.33.2359

  日期：——

  Novel 7-thiaprostaglandin E1 derivatives and congeners were synthesized by a stepwise three-component coupling process, which involves the introduction of α-side chains (thiols) and β-side chains (organocopper reagents) into (R)-4-tert-butyldimethylsilyloxy-2-cyclopentenone. Several acid derivatives of 7-thiaprostaglandin E1 were also prepared either by enzymatic or by chemical methods. The stereochemistry of these products was assigned on the basis of the results with chiral protected cyclopentenones and chiral ω-side chains. Some of these 7-thiaprostaglandin E1 congeners were found to exhibit more potent platelet aggregation-inhibitory activity than PGE1. The structure-activity relationship of these congeners is discussed.

  合成了一系列新型的7-硫前列腺素E1衍生物和同系物，采用一步法的三组分耦合过程，该过程涉及向(R)-4-叔丁基二甲基硅氧基-2-环戊烯酮引入α侧链（硫醇）和β侧链（有机铜试剂）。还通过酶法或化学方法制备了几种7-硫前列腺素E1的酸衍生物。这些产物的立体化学基于对手性保护的环戊烯酮和手性ω侧链的结果进行分配。发现某些7-硫前列腺素E1同系物的血小板聚集抑制活性比PGE1更强。文中讨论了这些同系物的结构-活性关系。