3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone

• 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: 3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone
• 英文别名: 3-Butyl-4-hydroxy-5-methyloxolan-2-one
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: LLALEXXCKCFLES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  3-butyl-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone 、 异戊酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-butyl-2-methyl-5-oxo-(2S,3S,4S)-tetrahydro-3-furanyl 3-methylbutanoate 、 <(3R,4R,5R)-3-butyl-4,5-dihydro-5-methyl-2-oxo-(3H)-4-furyl> 3-methylbutanoate
  参考文献：
  名称：

  Synthesis of Optically Active Butenolides andγ-Lactones by the Sharpless Asymmetric Dihydroxylation ofβ,γ-Unsaturated Carboxylic Esters

  摘要：

  DOI：

  10.1002/anie.199727501

文献信息

• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Total Syntheses of (−)-Grandinolide and (−)-Sapranthin by the Sharpless Asymmetric Dihydroxylation of Methyltrans-3-Pentenoate: Elucidation of the Stereostructure of (−)-Sapranthin
  作者：Christian Harcken、Reinhard Brückner、Elisabeth Rank

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2342::aid-chem2342>3.0.co;2-q

  日期：1998.11.2

  Methyl trans-3-pentenoate (7) was converted into the cis-substituted gamma-lactone 8 in a single step with 78 % ee. The derived enolate dilithio-8 was alkylated trans-selectively with primary iodoalkanes. with 1-iodobutane dilithio-8 afforded, after esterification with isovaleroyl chloride, the epi-blast mycinone 9, Dilithio-8 gave (-)-grandinolide (11) with 1-iodo-19-phenylnonadecane (20), A third trans-selective alkylation of dilithio-8 was undertaken with 16-iodo-1.5-hexadecadiene-7,9-diyne (21). This gave the gamma-lactone 12. which had the published relative configuration of (-)-sapranthin but different spectroscopic data, When the OH group of lactone 8 was inverted (to hydroxylactone 40) and the derived enolate dilithio-40 alkylated with iodide 21, lactone 41 resulted, Its H-1 and C-13 NMR spectra and the sign and value of optical rotation coincide with the data of natural sapranthin, These findings establish that (-)-sapranthin possesses the relative and absolute configuration of stereoformula 41. The synthesis of iodide 21 was performed via the dienoic carboxylic ester trans-23 which stemmed from the Claisen-Ireland rearrangement (27 --> 28/29)/esterification (28/29 --> 26)/Cope rearrangement (26 - 23) sequence shown in Scheme 5.
• PROCESSES AND HOST CELLS FOR GENOME, PATHWAY, AND BIOMOLECULAR ENGINEERING
  申请人：ENEVOLV, INC.

  公开号：US20160186168A1

  公开（公告）日：2016-06-30

  The present disclosure provides compositions and methods for genomic engineering.
• US9944925B2
  申请人：——

  公开号：US9944925B2

  公开（公告）日：2018-04-17
• Synthesis of Optically Active Butenolides andγ-Lactones by the Sharpless Asymmetric Dihydroxylation ofβ,γ-Unsaturated Carboxylic Esters
  作者：Christian Harcken、Reinhard Brückner

  DOI：10.1002/anie.199727501

  日期：1997.1.7