(4E)-3-hydroxy-2-methyl-4-hexenoate

• 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: (4E)-3-hydroxy-2-methyl-4-hexenoate
• 英文别名: 4-Hexenoic acid, 3-hydroxy-2-methyl-, methyl ester, (R*,R*)-；methyl (E)-3-hydroxy-2-methylhex-4-enoate
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: JEHGEKPSUMDBCP-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (4E)-3-hydroxy-2-methyl-4-hexenoate 在 lithium aluminium tetrahydride 作用下， 生成 (E)-2-methyl-4-hexene-1,3-diol
  参考文献：
  名称：

  Regiochemically and stereochemically defined synthesis of allylsilanes

  摘要：

  Allyl sulfides containing a siloxy or hydroxy group at appropriate positions were successfully converted by two methods into two types of allylsilanes with almost complete stereo- and regiocontrol. In one method, an allyllithium was generated from the siloxy compound after which the silyl group migrated from oxygen to the carbanionic site. The reaction of 4-[[(trimethylsilyl)oxy]methyl]-3-methyl-2-cyclohexenyl phenyl sulfide with lithium di-tert-butylbiphenylide (LDBB) led to an exclusive formation of (1R*,2R*)-2-methyl-2-(trimethylsilyl)-3-cyclohexene-1-methanol. The second method involved the silylation of an oxyanion-carbanion. Using this method, (1R*,4R*)-1-methyl-4-(trimethylsilyl)-2-cyclohexene-1-methanol was obtained by treating its lithium alkoxide with LDBB followed by silylation with chlorotrimethylsilane.

  DOI：

  10.1021/ja00073a018
• 作为产物：
  描述：

  巴豆醛 、 丙酸甲酯 在 lithium diisopropyl amide 作用下， 生成 (4E)-3-hydroxy-2-methyl-4-hexenoate
  参考文献：
  名称：

  Regiochemically and stereochemically defined synthesis of allylsilanes

  摘要：

  Allyl sulfides containing a siloxy or hydroxy group at appropriate positions were successfully converted by two methods into two types of allylsilanes with almost complete stereo- and regiocontrol. In one method, an allyllithium was generated from the siloxy compound after which the silyl group migrated from oxygen to the carbanionic site. The reaction of 4-[[(trimethylsilyl)oxy]methyl]-3-methyl-2-cyclohexenyl phenyl sulfide with lithium di-tert-butylbiphenylide (LDBB) led to an exclusive formation of (1R*,2R*)-2-methyl-2-(trimethylsilyl)-3-cyclohexene-1-methanol. The second method involved the silylation of an oxyanion-carbanion. Using this method, (1R*,4R*)-1-methyl-4-(trimethylsilyl)-2-cyclohexene-1-methanol was obtained by treating its lithium alkoxide with LDBB followed by silylation with chlorotrimethylsilane.

  DOI：

  10.1021/ja00073a018

文献信息

• Determination of the Relative Configurations in the Side Chains of the Antibiotics Hedamycin and Pluramycin A; Synthesis and NMR. Data of Suitable Model Compounds
  作者：Mario Ceroni、Urs Séquin

  DOI：10.1002/hlca.19820650133

  日期：1982.2.3

  spectra were measured and assigned. Comparison of these data with the spectra of the antibiotics hedamycin (1) and pluramycin A (2) allowed the determi-nation of the relative configurations in the side chains of these antibiotics. They were found to be (14R*,16S*,17R*,18S*) for hedamycin (1) and (14R*,16S*,17Z) for pluramycin A (2).

  通过2-甲基-2,4-己二酸甲酯的环氧化或通过Darzens缩合制备几种二环氧己酸和环氧己酸。它们的1 H-和13 C-NMR。光谱被测量并分配。将这些数据与抗生素合霉素（1）和普拉霉素A（2）的光谱进行比较，可以确定这些抗生素的侧链中的相对构型。发现它们对氦霉素（1）为（14 R *，16 S *，17 R *，18 S *）对于普拉霉素A（2为（14 R *，16 S *，17 Z））。）。
• 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。
• ABEN R. W.; SCHEEREN J. W., SYNTHESIS, 1978, NO 5, 400-402
  作者：ABEN R. W.、 SCHEEREN J. W.

  DOI：——

  日期：——
• Processes for the preparation of optically active compounds having plural chiral centers
  申请人：Chisso Corporation

  公开号：EP0428392B1

  公开（公告）日：1998-05-27
• US5348870A
  申请人：——

  公开号：US5348870A

  公开（公告）日：1994-09-20