(4S,5R)-4-(3-hydroxypentan-3-yl)-5-((-)-menthyloxy)-dihydrofuran-2(3H)-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4S,5R)-4-(3-hydroxypentan-3-yl)-5-((-)-menthyloxy)-dihydrofuran-2(3H)-one
• 英文别名: (4S,5R)-4-(3-hydroxypentan-3-yl)-5-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxolan-2-one
• 化学式: C₁₉H₃₄O₄
• 分子量: 326.477
• InChiKey: XLENGAAXTMKPPT-ORDFZIBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-戊醇 、 (5R)-(L-menthyloxy)-2(5H)-furanone 在 4,4'-二甲氧基二苯甲酮 作用下， 以61%的产率得到(4S,5R)-4-(3-hydroxypentan-3-yl)-5-((-)-menthyloxy)-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Parallel Microflow Photochemistry: Process Optimization, Scale-up, and Library Synthesis

  摘要：

  A novel, multimicrocapillary flow reactor (M mu CFR) was constructed and applied to a series of sensitized photoadditions involving 2(5H)-furanones. The reactor allowed for rapid and energy-, time-, and space-efficient sensitizer screening, process optimization, validation, scale-up, and library synthesis.

  DOI：

  10.1021/ol301773r

文献信息

• Highly diastereoselective addition of photochemically generated radicals to (5R)-(−)-menthyloxy-2[5H]-furanone - synthesis of(−)-terebic acid
  作者：Norbert Hoffmann

  DOI：10.1016/s0957-4166(00)86239-4

  日期：1994.5

  Photochemically generated ketyl and 2-dioxdanyl radicals are added with high diastereoselectivity (de > 95%) to (5R)-(-)-5-menthyloxy-2[5H]furanone. This reaction is used for the asymmetric synthesis of (-)-terebic acid. The double bond is attacked by the radicals on the ul-side.
• Stereoselective intermolecular addition of ketyl radicals generated from ketones by photoinduced electron transfer
  作者：Cédric Brulé、Norbert Hoffmann

  DOI：10.1016/s0040-4039(01)02089-5

  日期：2002.1

  Ketyl radicals were produced from ketones by photochemical electron transfer and subsequent proton transfer from tertiary amines. These radicals were stereoselectively added to (5R)-5-(-)-menthyloxy-2[5H]-furanone 1. Due to their low reactivity, the alpha -aminoalkyl radicals which were generated at the same time were not added to 1. The ketones were used in stoichiometric quantities. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Parallel Microflow Photochemistry: Process Optimization, Scale-up, and Library Synthesis
  作者：Alexander Yavorskyy、Oksana Shvydkiv、Norbert Hoffmann、Kieran Nolan、Michael Oelgemöller

  DOI：10.1021/ol301773r

  日期：2012.9.7

  A novel, multimicrocapillary flow reactor (M mu CFR) was constructed and applied to a series of sensitized photoadditions involving 2(5H)-furanones. The reactor allowed for rapid and energy-, time-, and space-efficient sensitizer screening, process optimization, validation, scale-up, and library synthesis.