(E)-6-(prop-1-en-1-yl)dihydro-2H-pyran-2,4(3H)-dione | 57012-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (E)-6-(prop-1-en-1-yl)dihydro-2H-pyran-2,4(3H)-dione
• 英文别名: 6-propenyl-dihydro-pyran-2,4-dione；(+/-)-6-trans-propenyl-dihydro-pyran-2,4-dione；(+/-)-6-trans-Propenyl-dihydro-pyran-2,4-dion；6-[(E)-prop-1-enyl]oxane-2,4-dione
• CAS: 57012-09-6
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: TYRPKRFNUGNVHN-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-Methoxy-2-((E)-propenyl)-2,3-dihydro-pyran-4-one 以 盐酸 、 苯 为溶剂， 以93%的产率得到(E)-6-(prop-1-en-1-yl)dihydro-2H-pyran-2,4(3H)-dione
  参考文献：
  名称：

  Synthesis of 3-oxo-δ-lactones via hetero-Diels-Alder reactions

  摘要：

  DOI：

  10.1016/s0040-4039(01)80241-0

文献信息

• Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis
  作者：Steffen Friedrich、Franziska Hemmerling、Frederick Lindner、Anna Warnke、Johannes Wunderlich、Gesche Berkhan、Frank Hahn

  DOI：10.3390/molecules21111443

  日期：——

  We describe the characterisation of the O-methyltransferase JerF from the late stages of jerangolid biosynthesis. JerF is the first known example of an enzyme that catalyses the formation of a non-aromatic, cyclic methylenolether. The enzyme was overexpressed in E. coli and the cell-free extracts were used in bioconversion experiments. Chemical synthesis gave access to a series of substrate surrogates

  我们描述了 jerangolid 生物合成后期的 O-甲基转移酶 JerF 的特征。JerF 是第一个已知的催化非芳香族环状亚甲基醚形成的酶的例子。该酶在大肠杆菌中过表达，无细胞提取物用于生物转化实验。化学合成提供了一系列覆盖广泛结构空间的底物替代物。酶促测定显示 JerF 具有广泛的底物耐受性和高区域选择性，这使其成为化学酶促合成应用的有吸引力的候选者，尤其适用于 4-甲氧基-5,6-二氢-2H-吡喃-2-one 的后期应用- 含有天然产物。
• Synthesis and evaluation of the molluscicidal activity of the 5,6-dimethyl-dihydro-pyran-2,4-dione and 6-substituted analogous
  作者：Laura Cristiane de Souza、Aldenir Feitosa dos Santos、Antônio Euzébio Goulart Sant'Ana、Dennis de Oliveira Imbroisi

  DOI：10.1016/j.bmc.2004.01.001

  日期：2004.3

  Five dihydro-piran-2,4-diones, including 5,6-dimethyl-dihydro-piran-2,4-dione one of the intermediates of the synthesis of caloverticilic acid, were synthesized and submitted to molluscicidal bioassay. The compound's yields varied from moderate to good (42%- 80%) and were achieved through the preparation of the dianion of ethyl acetoacetate, reaction with and aldehyde followed by hydrolysis of the ester (NaOH, H2O, 2 h, T.A.) and lactonization in acidic medium (HCl, 0degreesC). The 5,6-dimethyl-dihydro-piran-2,4-dione and three analogous dihydro-piran-2,4-diones 6-substituted,-phenyl, (4-methoxy-phenyl), and -propenyl, showed significant activities against the Biomphalaria glabrata egg masses, while the analogous 6-(3,4-dimethoxy-phenyl) was inactive as molluscicide. This activity is reported for the first time, extending the range of biological activities of this group. (C) 2004 Elsevier Ltd. All rights reserved.
• 717. Studies on compounds related to auxin-a and auxin-b. Part II. Preparation of analogues of auxin-b lactone
  作者：H. B. Henbest、E. R. H. Jones

  DOI：10.1039/jr9500003628

  日期：——
• CASTELLINO, S.;SIMS, J. J., TETRAHEDRON LETT., 1984, 25, N 22, 2307-2310
  作者：CASTELLINO, S.、SIMS, J. J.

  DOI：——

  日期：——
• US4418142A
  申请人：——

  公开号：US4418142A

  公开（公告）日：1983-11-29