ethyl E-2-methyl-3-hydroxyhex-4-enoate | 88662-89-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl E-2-methyl-3-hydroxyhex-4-enoate
• 英文别名: ethyl (E)-3-hydroxy-2-methylhex-4-enoate
• CAS: 88662-89-9；88662-90-2
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: FRBLIEWYWRNUIJ-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  5
• 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：

  ethyl E-2-methyl-3-hydroxyhex-4-enoate 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到(E)-2-Methyl-3-oxo-hex-4-enoic acid ethyl ester
  参考文献：
  名称：

  以色列松树皮，日本松球菌，雌性信息素的合成及田间生物测定

  摘要：

  我们报告松果球菌（2E，4E，8E）-4,6-二甲基-2,4,8-癸三烯-7-一（1）和（2E，4Z）的女性信息素的两个成分的首次合成，8E）-4,6-二甲基-2,4,8-癸三烯-7-一（2）利用Reformatzky和Wittig反应作为关键步骤。在松树林中对1和2以及单独的异构体的混合物进行了生物分析，表明E异构体1的活性比2高得多，并且对于捕食者也是海洛酮。

  DOI：

  10.1016/s0040-4039(00)73904-9
• 作为产物：
  描述：

  巴豆醛 、 2-溴丙酸乙酯 在 锌铜偶 作用下， 以 乙醚 为溶剂， 以84%的产率得到ethyl E-2-methyl-3-hydroxyhex-4-enoate
  参考文献：
  名称：

  以色列松树皮，日本松球菌，雌性信息素的合成及田间生物测定

  摘要：

  我们报告松果球菌（2E，4E，8E）-4,6-二甲基-2,4,8-癸三烯-7-一（1）和（2E，4Z）的女性信息素的两个成分的首次合成，8E）-4,6-二甲基-2,4,8-癸三烯-7-一（2）利用Reformatzky和Wittig反应作为关键步骤。在松树林中对1和2以及单独的异构体的混合物进行了生物分析，表明E异构体1的活性比2高得多，并且对于捕食者也是海洛酮。

  DOI：

  10.1016/s0040-4039(00)73904-9

文献信息

• Cobalt catalyzed regioselective allylation of 1,3-dicarbonyl compounds
  作者：Golak C. Maikap、M. Madhava Reddy、Manoj Mukhopadhyay、Beena Bhatia、Javed Iqbal

  DOI：10.1016/s0040-4020(01)85380-1

  日期：1994.1

  Catalytic amount of Cobalt(II) chloride in 1,2-dichloroethane promotes the allylation of 1,3-dicarbonyl compounds with allyl acetates in high yields. The allylation of pentane-2,4-dione is highly regioselective as compared with methylacetoacetate and ethyl 2-oxocyclopentanecarboxylate.

  催化量的1,2-二氯乙烷中的氯化钴（II）以高收率促进1,3-二羰基化合物与乙酸烯丙酯的烯丙基化。与乙酰乙酸甲酯和2-氧代环戊烷甲酸乙酯相比，戊烷-2,4-二酮的烯丙基化具有高度的区域选择性。
• Optically active compounds having plural chiral centers and the production thereof
  申请人：Chisso Corporation

  公开号：EP0428392A2

  公开（公告）日：1991-05-22

  Optically active compounds, having a plurality of chiral centres, have the general formulae: or in which R', R2 and R4 are the same or are different and each is an alkyl, alkenyl or alkynyl group having up to 40 carbon atoms, the carbon chain of which may contain one or more of halogen, cyano, oxygen, nitrogen, silicon, sulfur and substituted or unsubstituted benzene, cyclohexane, pyridine, pyrimidine, pyridazine, pyrazine, dioxane or bicyclooctane ring 5; R3 is an alkyl, alkenyl or alkynyl groups having 3 to 40 carbon atoms ; X is hydrogen or an alkanoyl group having 2 to 40 carbon atoms; and the carbon atom with the sign, *, is an asymmetic carbon.

  具有多个手性中心的光学活性化合物的通式为 或 其中 R'、R2 和 R4 相同或不同，且各自为具有多达 40 个碳原子的烷基、烯基或炔基，其碳链可包含一个或多个卤素、氰基、氧、氮、硅、硫和取代或未取代的苯、环己烷、吡啶、嘧啶、哒嗪、吡嗪、二氧杂环或双环辛烷环 5； R3 是具有 3 至 40 个碳原子的烷基、烯基或炔基； X 是氢或具有 2 至 40 个碳原子的烷酰基； 符号 * 的碳原子为异构碳。
• Long-acting contraceptive agents: Levonorgestrel esters of unsaturated acids
  作者：A.S.C. Wan、T.L. Ngiam、S.L. Leung、M.L. Go、C.G. Francisco、R. Freire、R. Hernandez、J.A. Salazar、E. Suarez、G.A. Garcia、O. Jimeno、J.A.Noguez A.、A.Acosta H.、R. Vlahov、V. Tarpanov、M. Boshkova-Ljapova、B. Milenkov、V. Stoilova、J. Vlahov、G. Snatzke

  DOI：10.1016/0039-128x(83)90105-8

  日期：1983.3

  Esters of levonorgestrel (13 beta-ethyl-17 beta-ethynyl-17 beta-hydroxygon-4-en-3-one) with a variety of unsaturated carboxylic acids have been synthesized for evaluation as potential long-acting, injectable contraceptive agents.
• Cobalt(II)-Catalyzed Conversion of Allylic Alcohols/Acetates to Allylic Amides in the Presence of Nitriles
  作者：Manoj Mukhopadhyay、M. Madhava Reddy、G. C. Maikap、Javed Iqbal

  DOI：10.1021/jo00114a013

  日期：1995.5

  Various secondary allylic alcohols or their acetates and tertiary allylic alcohols can be converted to the corresponding transposed allylic amides in the presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile. Tertiary alcohols undergo complete rearrangement whereas secondary ones afford a mixture of regioisomers. Moderate yields of amides are also obtained by reacting acrylonitrile with secondary alcohols in 1,2-dichloroethane. The presence of acetic anhydride or acetic acid is crucial to the formation of amides as the absence of the former affords no amides and the allylic alcohols are mainly recovered as regioisomeric mixtures. The regioselectivity during amide formation can be enhanced by using cobalt complexes 14-16 in acetic acid medium. Some preliminary studies indicate that these reactions are proceeding via an pi-allyl complex or tight ion pair rather than a [3,3] sigmatropic rearrangement of acetamidate obtained in a Pinner reaction.
• Antimicrobial metabolites produced by an intertidal Acremonium furcatum
  作者：Gabriela L. Gallardo、Matías Butler、Mariana L. Gallo、M. Alejandra Rodríguez、Marcos N. Eberlin、Gabriela M. Cabrera

  DOI：10.1016/j.phytochem.2006.07.028

  日期：2006.11

  In a screening for antimicrobial metabolites, amides Of D-allo-and L-isoleucine derivatives were isolated from the culture of a marine strain of Acremonium furcatum. Structural elucidation of these compounds was performed by analysis of spectroscopic data and confirmed by synthesis. All of the compounds, natural and synthetic intermediates, were bioassayed against bacteria and phytopathogenic fungi, with many showing remarkable antifungal activities. (c) 2006 Elsevier Ltd. All rights reserved.