4-benzyl-5-hydroxyfuranone | 112895-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-benzyl-5-hydroxyfuranone
• 英文别名: 5-hydroxy-4-benzylbutenolide；4-benzyl-5-hydroxyfuran-2(5H)-one；3-benzyl-2-hydroxy-2H-furan-5-one
• CAS: 112895-74-6
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: KKZHYMQNFJWJGU-UHFFFAOYSA-N

物化性质

• 沸点：
  427.1±45.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  4-benzyl-5-hydroxyfuranone 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以24%的产率得到benzyl-maleic acid-anhydride
  参考文献：
  名称：

  Rh /双膦-硫脲催化马来酸酐的不对称加氢反应：手性琥珀酸酐的高效结构

  摘要：

  成功开发了Rh /双膦-硫脲（ZhaoPhos）在温和条件下催化的各种3-取代的马来酸酐的不对称加氢反应。广泛地将3-烷基和3-芳基马来酸酐进行氢化以制得...

  DOI：

  10.1039/c7cc01626c
• 作为产物：
  描述：

  苯丙醛 、 乙醛酸 在 哌啶盐酸盐 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 40.0h， 以78%的产率得到4-benzyl-5-hydroxyfuranone
  参考文献：
  名称：

  Synthesis of 4-benzyl-3-phenylbutenolide natural products

  摘要：

  The first total synthesis of eutypoid A and a new synthesis of racemic microperfuranone and gymnoascolide A have been achieved. The key steps in our synthetic strategy involve a Suzuki coupling reaction to install the C3 aryl ring and a Mannich-type reaction for the construction of the 4-benzylbutenolide core. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.101

文献信息

• PPAR-gamma ACTIVATOR
  申请人：KOJUN JAPAN CO., LTD.

  公开号：US20170105965A1

  公开（公告）日：2017-04-20

  The present invention provides A PPARγ activator comprising a butenolide compound represented by the formula (1) or a pharmaceutically acceptable salt thereof: wherein R 1 represents a hydrogen atom, a phosphate group, a fatty acid group, an alkyl group having 1 to 4 carbon atoms and optionally having a substituent or a sugar residue optionally having a substituent, and R 2 represents a phenyl group, a methylphenyl group, a dimethylphenyl group, an ethylphenyl group, a benzyl group, a methylbenzyl group, a dimethylbenzyl group, an ethylbenzyl group, a phenethyl group, a methylphenethyl group, a dimethylphenethyl group, or an ethylphenethyl group.

  本发明提供了一种PPARγ激活剂，包括由式（1）表示的丁烯内酯化合物或其药学上可接受的盐：其中，R1表示氢原子、磷酸盐基团、脂肪酸基团、具有1至4个碳原子的烷基基团，并且可以选择地具有取代基或糖残基，R2表示苯基、甲基苯基、二甲基苯基、乙基苯基、苄基、甲基苄基、二甲基苄基、乙基苄基、苯乙基、甲基苯乙基、二甲基苯乙基或乙基苯乙基。
• Stereodivergent Synthesis of Enantioenriched 2-Pyrrolidones via Diastereoselective Hydrogenation of α,β-Unsaturated γ-Lactams
  作者：Siyuan Guo、Baode Ma、Gen-Qiang Chen、Xumu Zhang

  DOI：10.1021/acs.orglett.3c00532

  日期：——

  Synthesis of optically enriched racetam analogues was achieved via highly remote diastereocontrolled and enantiocontrolled Pd/C-catalyzed hydrogenation of α,β-unsaturated γ-lactams. Various mono- and disubstituted 2-pyrrolidones were obtained in excellent yields and stereoselectivities, and a concise and large-scale synthesis of brivaracetam was developed from inexpensive l-2-aminobutyric acid. Surprisingly

  通过高度远程非对映控制和对映控制 Pd/C 催化的α,β-不饱和 γ-内酰胺氢化，合成了光学富集的 racetam 类似物。以优异的收率和立体选择性获得了各种单取代和双取代的 2-吡咯烷酮，并且从廉价的l -2-氨基丁酸开发了一种简明和大规模的布瓦西坦合成。令人惊讶的是，通过修饰远程功能化立体中心和添加剂观察到立体发散氢化，这将提供手性 racetam 合成的替代立体化学选择。
• Analogs of .gamma.-hydroxybutyric acid. Synthesis and binding studies
  作者：Jean Jacques Bourguignon、Angele Schoenfelder、Martine Schmitt、Camille Georges Wermuth、Viviane Hechler、Brigitte Charlier、Michel Maitre

  DOI：10.1021/jm00400a001

  日期：1988.5

  Substituted 4-hydroxybutyric (GHB) or trans-4-hydroxycrotonic acids (T-HCA) and structurally related compounds were synthesized and submitted to [3H]GHB binding. Structure-activity relationships studies highlighted for [3H]GHB binding (a) the necessity of a nonlactonic, relatively extended conformation of the gamma-hydroxybutyric chain, (b) the existence of some bulk tolerance in the vicinity of the hydroxyl group, and (c) the high sensitivity toward isosteric replacements of the carboxyl or the hydroxyl groups. T-HCA has been recently identified as a naturally occurring substance in the central nervous system (CNS) and shows a better affinity than GHB. Our findings are in favor of the presence in the CNS of specific GHB binding sites, which are different from the GABA and the picrotoxin binding sites, and for which T-HCA may be an endogenous ligand.
• Graziano, M. Liliana; Lesce, M. Rosaria; Cinotti, Angela, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1833 - 1840
  作者：Graziano, M. Liliana、Lesce, M. Rosaria、Cinotti, Angela、Scarpati, Rachele

  DOI：——

  日期：——
• US9943501B2
  申请人：——

  公开号：US9943501B2

  公开（公告）日：2018-04-17