5-羟基辛酸甲酯 | 101853-49-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-羟基辛酸甲酯
• 英文名称: 5-Hydroxyoctanoate methyl ester
• 英文别名: methyl 5-hydroxyoctanoate；5-Hydroxy-octansaeuremethylester；5-Hydroxyoctansaeure-methylester；Methyl 5-hydroxyoctanoate
• CAS: 101853-49-0
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: XMQPWFCBPDENRU-UHFFFAOYSA-N

物化性质

• 沸点：
  233.3±23.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)
• LogP：
  1.480 (est)
• 保留指数：
  1994

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-羟基辛酸甲酯 在 咪唑 、 三甲基铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 72.25h， 生成 S-(2-acetamidoethyl) 5-[tert-butyl(dimethyl)silyl]oxyoctanethioate
  参考文献：
  名称：

  Biosynthesis of the Hypotensive Metabolite Oudenone by Oudemansiella radicata. 1. Intact Incorporation of a Tetraketide Chain Elongation Intermediate

  摘要：

  The biosynthesis of the fungal metabolite oudenone (1) was investigated in cultures of Oudemansiella radicata. Feeding experiments using C-13 and H-2-labeled precursors, as well as NMR analyses of the labeled metabolite, suggested a polyketide origin. The incorporation of six acetate units into the carbon skeleton of 1 was observed when cultures were fed the N-acetylcysteamine thioester derivative of C-13-labeled acetate. Labeling of oudenone (1) from [1,4-C-13(2)]succinate or L-[5-C-13]-glutamic acid was not observed, whereas the pattern of C-13 labeling from [2,3-C-13(2)]succinate was identical to that observed with [1,2-C-13(2)]acetate. The proposed advanced intermediate (5S)-5-hydroxyoctanoic acid (2) was synthesized as the deuterium labeled N-acetylcysteamine thioester derivative (S)-19 and successfully incorporated into 1. A biosynthetic scheme and cyclization mechanism, consistent with the experimental data, is proposed.

  DOI：

  10.1021/jo00126a050
• 作为产物：
  描述：

  methyl 5-oxooctanoate 在 aluminum isopropoxide 作用下， 生成 5-羟基辛酸甲酯
  参考文献：
  名称：

  Lardelli,G. et al., Recueil des Travaux Chimiques des Pays-Bas, 1967, vol. 86, p. 481 - 503

  摘要：

  DOI：

文献信息

• [EN] HALOALKENE COMPOUNDS, PROCESS FOR THEIR PRODUCTION AND PESTICIDES CONTAINING THEM<br/>[FR] HALOALCENES, PROCEDE DE PRODUCTION D'HALOALCENES ET PESTICIDES CONTENANT CES HALOALCENES
  申请人：ISHIHARA SANGYO KAISHA

  公开号：WO2004052872A1

  公开（公告）日：2004-06-24

  ABSTRACT A novel haloalkene compound represented by the formula (I), useful as an active ingredient of a pesticide, is presented: wherein each of X1 and X2 is halogen, Y is a hydrogen atom, halogen, alkyl or the like, n is from 0 to 5, A is an oxygen atom or a sulfur atom, G is a hydrogen atom, alkyl, acyl or the like, and Q is a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, alkyl which may be substituted by W, alkenyl which may be substituted by W, alkynyl which may be substituted by W, or cycloalkyl which may be substituted by W, wherein W is halogen, alkoxy, alkylthio, hydroxyl, cyano, nitro or phenyl which may be substituted.

  摘要：提供了一种新型卤烯化合物，其化学式表示为（I），可作为杀虫剂的活性成分：其中X1和X2中的每一个是卤素，Y是氢原子，卤素，烷基或类似物，n为0至5，A是氧原子或硫原子，G是氢原子，烷基，酰基或类似物，Q是一个含有5至12个成员的杂环基团（杂环基团可能被取代），其中可选地包含从氧原子、硫原子和氮原子中选择的一个杂原子，烷基可被W取代，烯基可被W取代，炔基可被W取代，或环烷基可被W取代，其中W是卤素，烷氧基，烷基硫基，羟基，氰基，硝基或可能被取代的苯基。
• Total Synthesis and Configurational Assignment of the Marine Natural Product Haliclamide
  作者：Bernhard Pfeiffer、Sandra Speck-Gisler、Luzi Barandun、Ursula Senft、Claire de Groot、Irène Lehmann、Walter Ganci、Jürg Gertsch、Karl-Heinz Altmann

  DOI：10.1021/jo3027643

  日期：2013.3.15

  stereoisomers with literature data for the natural product, the configuration of the previously unassigned stereocenters at C9 and C20 of haliclamide could be determined to be S for both carbons. The absolute configuration of haliclamide thus is 2S, 9S, 14R, 20S. The antiproliferative activity of synthetic haliclamide against several human cancer cell lines was found to be in the high μM range. The

  在环化的基础上，通过闭环烯烃复分解合成了海洋天然产物卤代酰胺。使用用于组装二烯前体以进行复分解反应的四个结构单元中的两个的任一种的对映异构体，还制备了卤代酰胺的三种非天然异构体。根据各个立体异构体的1 H和13 C NMR光谱与天然产物的文献数据进行比较，可以确定先前未分配的卤代酰胺的C9和C20立体中心的构型对于两个碳都是S。因此，卤代酰胺的绝对构型为2 S，9 S，14 R，20 S。发现合成的哈利酰胺对几种人癌细胞系的抗增殖活性处于高μM范围内。该化合物没有抗真菌或抗生素活性。
• Lardelli,G. et al., Recueil des Travaux Chimiques des Pays-Bas, 1967, vol. 86, p. 481 - 503
  作者：Lardelli,G. et al.

  DOI：——

  日期：——
• Biosynthesis of the Hypotensive Metabolite Oudenone by Oudemansiella radicata. 1. Intact Incorporation of a Tetraketide Chain Elongation Intermediate
  作者：Youla S. Tsantrizos、Fei Zhou、Parsa Famili、Xianshu Yang

  DOI：10.1021/jo00126a050

  日期：1995.10

  The biosynthesis of the fungal metabolite oudenone (1) was investigated in cultures of Oudemansiella radicata. Feeding experiments using C-13 and H-2-labeled precursors, as well as NMR analyses of the labeled metabolite, suggested a polyketide origin. The incorporation of six acetate units into the carbon skeleton of 1 was observed when cultures were fed the N-acetylcysteamine thioester derivative of C-13-labeled acetate. Labeling of oudenone (1) from [1,4-C-13(2)]succinate or L-[5-C-13]-glutamic acid was not observed, whereas the pattern of C-13 labeling from [2,3-C-13(2)]succinate was identical to that observed with [1,2-C-13(2)]acetate. The proposed advanced intermediate (5S)-5-hydroxyoctanoic acid (2) was synthesized as the deuterium labeled N-acetylcysteamine thioester derivative (S)-19 and successfully incorporated into 1. A biosynthetic scheme and cyclization mechanism, consistent with the experimental data, is proposed.