methyl 3-hydroxy-oct-7-enoate | 128940-63-6

• 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 3-hydroxy-oct-7-enoate
• 英文别名: 7-Octenoic acid, 3-hydroxy-, methyl ester；methyl 3-hydroxyoct-7-enoate
• CAS: 128940-63-6
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: CNRMLAWDUPNQHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  methyl 3-hydroxy-oct-7-enoate 在 palladium dichloride 吡啶 、 lithium aluminium tetrahydride 、 氧气 、 copper(l) chloride 作用下， 以 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (3R,S,7R,S)-octane-1,3,7-triol
  参考文献：
  名称：

  Isolation, Identification, and Enantioselective Synthesis of Octane-1,3,7-triol:  Determination of Its Absolute Configuration

  摘要：

  Extracts obtained by solid-phase extraction from apples were separated by multilayer countercurrent chromatography. In the most polar fractions, the novel octane-1,3,7-triol was identified by H-1 and C-13 NMR as well as LC-MS and by comparison with the synthesized racemic reference compound. Resolution of the enantiomers was achieved after acetylation of the triol followed by GC separation. The enantioselective synthesis of the stereoisomers of octane-1,3,7-triol was performed using the building blocks (R)- and (R,S)-butane-1,3-diol and (S)- and (R,S)-butane-1,2,4-triol, Comparison with the isolated products indicated that the natural compound consisted of a mixture of (3R,7S)- and (SR,7R)-octane-1,3,7-triol in a ratio of 2:3. Since the C3 chiral center is enantiomerically pure, the triol might be biogenetically related to the known antimicrobial (R)-(+)-octane-1,3 -diol, the major volatile compound of some apple cultivars.

  DOI：

  10.1021/np980094e
• 作为产物：
  描述：

  5-己烯-1-醇 在 phosphorus pentoxide 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl 3-hydroxy-oct-7-enoate
  参考文献：
  名称：

  Isolation, Identification, and Enantioselective Synthesis of Octane-1,3,7-triol:  Determination of Its Absolute Configuration

  摘要：

  Extracts obtained by solid-phase extraction from apples were separated by multilayer countercurrent chromatography. In the most polar fractions, the novel octane-1,3,7-triol was identified by H-1 and C-13 NMR as well as LC-MS and by comparison with the synthesized racemic reference compound. Resolution of the enantiomers was achieved after acetylation of the triol followed by GC separation. The enantioselective synthesis of the stereoisomers of octane-1,3,7-triol was performed using the building blocks (R)- and (R,S)-butane-1,3-diol and (S)- and (R,S)-butane-1,2,4-triol, Comparison with the isolated products indicated that the natural compound consisted of a mixture of (3R,7S)- and (SR,7R)-octane-1,3,7-triol in a ratio of 2:3. Since the C3 chiral center is enantiomerically pure, the triol might be biogenetically related to the known antimicrobial (R)-(+)-octane-1,3 -diol, the major volatile compound of some apple cultivars.

  DOI：

  10.1021/np980094e

文献信息

• 2,6-Disubstituted Tetrahydropyrans by Tandem Cross-Metathesis/Iodocyclisation
  作者：Marie-Aude Hiebel、Béatrice Pelotier、Peter Goekjian、Olivier Piva

  DOI：10.1002/ejoc.200700902

  日期：2008.2

  A new approach to 2,6-disubstituted tetrahydropyrans by a tandem cross-metathesis/iodocyclisation reaction has been developed. The stereochemical outcome of the cyclisation reactions has been studied for different substrates. This sequence has allowed the preparation of a series of cis- and trans-2,6-disubstituted analogues of the tetrahydropyran subunit of bistramide A.(© Wiley-VCH Verlag GmbH & Co

  已经开发出一种通过串联交叉复分解/碘环化反应制备 2,6-二取代四氢吡喃的新方法。已针对不同底物研究了环化反应的立体化学结果。该序列允许制备双酰胺 A 的四氢吡喃亚基的一系列顺式和反式 2,6-二取代类似物。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Photo‐ and Cobalt‐Catalyzed Synthesis of Heterocycles via Cycloisomerization of Unactivated Olefins
  作者：Henry Lindner、Willi M. Amberg、Tristano Martini、David M. Fischer、Eléonore Moore、Erick M. Carreira

  DOI：10.1002/anie.202319515

  日期：2024.5.6

  A general, intramolecular cycloisomerization of unactivated olefins with pendant N-, O-, and C- nucleophiles is reported. The reaction proceeds under mild conditions, yielding a number of different heterocycles including, but not limited to, pyrrolidines, piperidines, oxazolidinones, and lactones. Use of both a benzothiazinoquinoxaline as organophotocatalyst and a Co-salen catalyst obviates the need

  报道了未活化烯烃与侧链N -、 O - 和C - 亲核试剂的一般分子内环异构化。该反应在温和条件下进行，产生许多不同的杂环，包括但不限于吡咯烷、哌啶、恶唑烷酮和内酯。使用苯并噻嗪喹喔啉作为有机光催化剂和Co-salen催化剂消除了对化学计量氧化剂或还原剂的需要。
• A One-Pot Reformatsky/Cyclopropanation Sequence Induced by Diethylzinc
  作者：Marie-France Laroche、Damien Belotti、Janine Cossy

  DOI：10.1021/ol048142b

  日期：2005.1.1

  A one-pot Reformatsky/cyclopropanation sequence induced by diethylzinc allows the transformation of omega-unsaturated ketones and aldehydes to omega-cyclopropyl alcohols.
• Isolation, Identification, and Enantioselective Synthesis of Octane-1,3,7-triol:  Determination of Its Absolute Configuration
  作者：Till Beuerle、Sonja Engelhard、Carlo Bicchi、Wilfried Schwab

  DOI：10.1021/np980094e

  日期：1999.1.1

  Extracts obtained by solid-phase extraction from apples were separated by multilayer countercurrent chromatography. In the most polar fractions, the novel octane-1,3,7-triol was identified by H-1 and C-13 NMR as well as LC-MS and by comparison with the synthesized racemic reference compound. Resolution of the enantiomers was achieved after acetylation of the triol followed by GC separation. The enantioselective synthesis of the stereoisomers of octane-1,3,7-triol was performed using the building blocks (R)- and (R,S)-butane-1,3-diol and (S)- and (R,S)-butane-1,2,4-triol, Comparison with the isolated products indicated that the natural compound consisted of a mixture of (3R,7S)- and (SR,7R)-octane-1,3,7-triol in a ratio of 2:3. Since the C3 chiral center is enantiomerically pure, the triol might be biogenetically related to the known antimicrobial (R)-(+)-octane-1,3 -diol, the major volatile compound of some apple cultivars.