(4S,5S)-5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one | 356060-07-6

• 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: (4S,5S)-5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one
• 英文别名: 4-hydroxy-5-methyl-5-(4-methylpent-3-en-1-yl)dihydrofuran-2(3H)-one；(4S,5S)-4-hydroxy-5-methyl-5-(4-methylpent-3-enyl)oxolan-2-one
• CAS: 356060-07-6
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: JMWBTPQEGMTXKP-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (4S,5S)-5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 在 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 silver trifluoromethanesulfonate 、 对苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以61%的产率得到(3aS,8aS)-5,5,8a-trimethylhexahydrofuro[3,2-b]oxepin-2(3H)-one
  参考文献：
  名称：

  非对映体化环氧化和硒催化的氧化环化合成（+）-希腊烟草内酯

  摘要：

  从容易获得的（R）-芳樟醇开始发展C 11-杂环类（+）-希腊烟草内酯的不对称合成。该合成包括四个步骤，其特征在于使用钒，钯和硒催化的环化反应生成非对映体化环氧化和氧化四氢吡喃。

  DOI：

  10.1021/acs.orglett.7b00484
• 作为产物：
  描述：

  1,4-戊二醇 在 正丁基锂 、 草酰氯 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 生成 (4S,5S)-5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one
  参考文献：
  名称：

  The samarium(II)-mediated intermolecular couplings of ketones and β-alkoxyacrylates: a short asymmetric synthesis of an antifungal γ-butyrolactone

  摘要：

  The samarium(II) iodide-mediated coupling of ketones with beta-alkoxyacrylatcs gives beta-hydroxy-gamma-butyrolactones in moderate yield. The process has been applied to the asymmetric synthesis of an antifungal, gamma-butyrolactone natural product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.027

文献信息

• Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
  作者：Carmen I. Viturro、Marta S. Maier、Carlos A. Stortz、Juana R. de la Fuente

  DOI：10.1016/s0957-4166(01)00163-x

  日期：2001.5

  Two diastereomeric furanones, (4S.5S)-5-(4'-methyl-3'-pentenyl)-4-hydroxy and (4S,5R)5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana, The relative stereochemistries of 1 and 2 were ascertained from NOESY NMR dat;l and confirmed by a combination of molecular modeling (molecular mechanics and ab initio molecular orbital calculations) and NMR data. Comparison between experimental and calculated H-1-H-1 vicinal coupling constants revealed that both furanones exist in an equilibrium of two stable conformers of the five-membered ring. Application of Mosher's method suggests that both diastereomeric furanones have the same (S)-configuration at C-(4) and are epimers at C-(5). Furanones 1 and 2 showed antifungal activity against the pathogenic fungus Cladosporium cucumerinum. (C) 2001 Elsevier Science Ltd. All rights reserved.
• The samarium(II)-mediated intermolecular couplings of ketones and β-alkoxyacrylates: a short asymmetric synthesis of an antifungal γ-butyrolactone
  作者：Nessan J. Kerrigan、Tejas Upadhyay、David J. Procter

  DOI：10.1016/j.tetlet.2004.10.027

  日期：2004.11

  The samarium(II) iodide-mediated coupling of ketones with beta-alkoxyacrylatcs gives beta-hydroxy-gamma-butyrolactones in moderate yield. The process has been applied to the asymmetric synthesis of an antifungal, gamma-butyrolactone natural product. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of (+)-Greek Tobacco Lactone via a Diastereoablative Epoxidation and a Selenium-Catalyzed Oxidative Cyclization
  作者：Stefan Leisering、Iker Riaño、Christian Depken、Leona J. Gross、Manuela Weber、Dieter Lentz、Reinhold Zimmer、Christian B. W. Stark、Alexander Breder、Mathias Christmann

  DOI：10.1021/acs.orglett.7b00484

  日期：2017.3.17

  available (R)-linalool. The synthesis is comprised of four operations and features a diastereoablative epoxidation and an oxidative tetrahydropyran formation using vanadium-, palladium-, and selenium-catalyzed cyclizations.

  从容易获得的（R）-芳樟醇开始发展C 11-杂环类（+）-希腊烟草内酯的不对称合成。该合成包括四个步骤，其特征在于使用钒，钯和硒催化的环化反应生成非对映体化环氧化和氧化四氢吡喃。