(4S,5R)-4-(2-hydroxypropan-2-yl)-5-((-)-menthyloxy)-dihydrofuran-2(3H)-one | 78597-75-8

• 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-(2-hydroxypropan-2-yl)-5-((-)-menthyloxy)-dihydrofuran-2(3H)-one
• 英文别名: 4-(2'-hydroxy-2'-propyl)-5-(-)-menthyloxyfuranone；(4S,5R)-4-(2-hydroxypropan-2-yl)-5-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxolan-2-one
• CAS: 78597-75-8
• 化学式: C₁₇H₃₀O₄
• 分子量: 298.423
• InChiKey: SQCWKYNUKODSEY-JTTNIQEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-(2-hydroxypropan-2-yl)-5-((-)-menthyloxy)-dihydrofuran-2(3H)-one 在 盐酸 、 氢氧化钾 、 对甲苯磺酸 、 臭氧 作用下， 以 乙酸乙酯 为溶剂， 反应 29.67h， 生成 (-)-(S)-2,2-dimethyl-5-oxotetrahydro-3-furancarboxylic acid
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)86239-4
• 作为产物：
  描述：

  (5R)-(L-menthyloxy)-2(5H)-furanone 、 异丙醇 在 二叔丁基过氧化物 作用下， 反应 4.0h， 以99%的产率得到(4S,5R)-4-(2-hydroxypropan-2-yl)-5-((-)-menthyloxy)-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  异丙醇和正丁醛与 (5R)-(l-薄荷氧基)呋喃-2(5H)-one 的立体有择自由基加成

  摘要：

  PriOH 和正丁醛与 (5R)-5-(1-薄荷氧基)呋喃-2(5H)-one 的自由基加成在呋喃酮环的 4 位发生区域和非对映特异性。

  DOI：

  10.1007/bf00702401

文献信息

• Stereospecific radical addition of isopropanol andn-butanal to (5R)-(l-menthyloxy)furan-2(5H)-one
  作者：Yu. N. Belokon'、K. A. Kochetkov、M. A. Moskalenko、N. I. Raevsky、T. F. Savel'eva、V. I. Tararov、T. D. Churkina

  DOI：10.1007/bf00702401

  日期：1995.3

  The radical addition of PriOH andn-butanal to (5R)-5-(l-menthyloxy)furan-2(5H)-one occurs regio- and diastereospecifically at position 4 of the furanone ring.

  PriOH 和正丁醛与 (5R)-5-(1-薄荷氧基)呋喃-2(5H)-one 的自由基加成在呋喃酮环的 4 位发生区域和非对映特异性。
• Photosensitized addition of isopropanol to furanones in a continuous-flow dual capillary microreactor
  作者：Alexander Yavorskyy、Oksana Shvydkiv、Kieran Nolan、Norbert Hoffmann、Michael Oelgemöller

  DOI：10.1016/j.tetlet.2010.11.018

  日期：2011.1

  A novel continuous-flow photoreactor with parallel capillaries was constructed and successfully tested for the DMBP-sensitized addition of isopropanol to furanones. Complete conversions were achieved after a maximum of 10 min of irradiation with a single 350 nm lamp. The results were compared to analogous batch experiments using a conventional Rayonet chamber reactor equipped with 16 UVA lamps. The capillary tower generally showed higher space-time yields. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• 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.