4(S)-Benzoyloxy-5(S)-methyl-2(3H)-dihydrofuranone | 152321-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4(S)-Benzoyloxy-5(S)-methyl-2(3H)-dihydrofuranone
• 英文别名: 4-benzoyloxy-5-methyl-2(3H)-furanone；[(2S,3S)-2-methyl-5-oxooxolan-3-yl] benzoate
• CAS: 152321-91-0
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: DLPMFDZKZZMTFW-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4(S)-Benzoyloxy-5(S)-methyl-2(3H)-dihydrofuranone 在 氨 作用下， 以 甲醇 为溶剂， 以88%的产率得到(S)-(+)-β-angelica lactone
  参考文献：
  名称：

  Stereocontrolled synthesis of the 4-hydroxy-5-methyl-2(3H)-dihydrofuranone isomers

  摘要：

  A synthesis of all four stereoisomers of 4-hydroxy-5-methyl-2(3H)-dihydrofuranone was achieved in 6 or 7 steps with an overall yield of 19% to 23% from a common starting material. The source of chirality being derived from stereoselective bakers' yeast reductions of carbonyl groups.

  DOI：

  10.1016/s0040-4020(01)85744-6
• 作为产物：
  描述：

  Ethyl 3(R,S)-benzoyloxy-4-oxopentanoate 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 108.0h， 生成 4(S)-Benzoyloxy-5(S)-methyl-2(3H)-dihydrofuranone
  参考文献：
  名称：

  Stereocontrolled synthesis of the 4-hydroxy-5-methyl-2(3H)-dihydrofuranone isomers

  摘要：

  A synthesis of all four stereoisomers of 4-hydroxy-5-methyl-2(3H)-dihydrofuranone was achieved in 6 or 7 steps with an overall yield of 19% to 23% from a common starting material. The source of chirality being derived from stereoselective bakers' yeast reductions of carbonyl groups.

  DOI：

  10.1016/s0040-4020(01)85744-6

文献信息

• Formation of 3-acyloxy-γ-butyrolactones from 4-pentenols in vanadium-catalyzed oxidations
  作者：Matthias Amberg、Maike Dönges、Georg Stapf、Jens Hartung

  DOI：10.1016/j.tet.2014.05.011

  日期：2014.8

  O-Acyl derivatives of 3-hydroxy-gamma-butyrolactone are formed in up to 20% yield as by-products from 1-alkyl- and 1-phenyl-substituted 4-pentenols and tert-butyl hydroperoxide (TBHP) in vanadium-catalyzed synthesis of (tetrahydrofuran-2-yl)-methanols. The lactones are secondary products formed from (tetrahydrofuran-2-yl)-methanols via hydrogen atom abstraction in positions 4 and 5, as derived from experiments starting from deuterium-labeled alkenols. Stereocenters at tetrahydrofuran carbon 2 and the proximate hydroxyl carbon of the alkanol side chain retain configuration in the course of oxidative tetrahydrofuran conversion. In an atmosphere of nitrogen or argon, no gamma-butyrolactone formation occurs, pointing to dioxygen as terminal oxidant for the secondary oxidation. Adding cyclohexa-1,4-diene or gamma-terpinene to a solution of a 4-pentenol, TBHP, and a vanadium catalyst exposed to air inhibits formation of gamma-butyrolactones. A third approach to prevent gamma-butyrolactones from being formed in oxidative 4-pentenol cyclization uses cis-2,6-bis-(methanol)-piperidine instead of N-salicylidene-ortho-aminophenol as tridentate auxiliary for the vanadium catalyst. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of solamin type mono-THF acetogenins using cross-metathesis
  作者：Hiroyuki Konno、Hidefumi Makabe、Yasunao Hattori、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2010.08.028

  日期：2010.10

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereocontrolled synthesis of the 4-hydroxy-5-methyl-2(3H)-dihydrofuranone isomers
  作者：Carlos A.M. Afonso、M.Teresa Barros、Licio S. Godinho、Christopher D. Maycock

  DOI：10.1016/s0040-4020(01)85744-6

  日期：1993.1

  A synthesis of all four stereoisomers of 4-hydroxy-5-methyl-2(3H)-dihydrofuranone was achieved in 6 or 7 steps with an overall yield of 19% to 23% from a common starting material. The source of chirality being derived from stereoselective bakers' yeast reductions of carbonyl groups.