(3R,4R)-二氢-3,4-二羟基-3-甲基-2(3H)-呋喃酮 | 18465-71-9

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (3R,4R)-二氢-3,4-二羟基-3-甲基-2(3H)-呋喃酮
• 英文名称: (3R,4R)-3,4-dihydroxy-3-methyl-4,5-dihydro-2(3H)-furanone
• 英文别名: (2R,3R)-2,3-dihydroxy-2-methyl-γ-butyrolactone；(-)-(3R,4R)-3,4-dihydroxy-3-methyldihydrofuran-2-one；(3R,4R)-3,4-dihydroxy-3-methyl-dihydro-furan-2-one；(2S,3S)-2,3,4-trihydroxy-2-methylbutan-1,4-olide；(3R,4R)-3,4-dihydroxy-3-methylbutyrolactone；(-)-2-C-methyl-D-erythrono-1,4-lactone；(3R,4R)-3,4-Dihydroxy-3-methyloxolan-2-one
• CAS: 18465-71-9
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: OHTGZAWPVDWARE-NQXXGFSBSA-N

物化性质

• 熔点：
  113 °C
• 沸点：
  254.0±7.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (3R,4R)-二氢-3,4-二羟基-3-甲基-2(3H)-呋喃酮 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 3-O-Caffeoyl-2-C-methyl-D-erythrono-1,4-lactone
  参考文献：
  名称：

  Marco, J. Alberto; Carda, Miguel; Gonzalez, Florenci, Anales de Quimica, 1995, vol. 91, # 1-2, p. 103 - 112

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-(3R,4R)-acetic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以91%的产率得到(3R,4R)-二氢-3,4-二羟基-3-甲基-2(3H)-呋喃酮
  参考文献：
  名称：

  An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

  摘要：

  Saccharinic acid lactone (-)-1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (+/-)-3 has been carried out to obtain (-)-1a in 46% yield with 99% ee and diacetyl lactone (+)-3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (+/-)-1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (-)-7 in 31% yield with 99% ee and (+)-1a in 63% yield. The conversion of (-)-1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.025

文献信息

• Green aldose isomerisation: 2-C-methyl-1,4-lactones from the reaction of Amadori ketoses with calcium hydroxide
  作者：David J. Hotchkiss、Raquel Soengas、Kathrine V. Booth、Alexander C. Weymouth-Wilson、Vanessa Eastwick-Field、George W.J. Fleet

  DOI：10.1016/j.tetlet.2006.11.137

  日期：2007.1

  Saccharinic acids, branched 2-C-methyl-aldonic acids, may be accessed via a green procedure from aldoses by sequential conversion to an Amadori ketose and treatment with calcium hydroxide; D-galactose and D-glucose are converted to 2-C-methyl-D-lyxono-1,4-lactone (with a small amount of 2-C-methyl-D-xylono-1,4-lactone) and 2-C-methyl-D-ribono-1,4-lactone. Inversion of configuration at C-4 of the branched lactones allows access to 2-C-methyl-L-ribono-1,4-lactone and 2-C-methyl-L-lyxono-1,4-lactone, respectively. D-Xylose affords 2-C-methyl-D-threono-1,4-lactone and 2-C-methyl-D-erythrono-1,4-lactone, whereas L-arabinose, under similar conditions, gave the enantioiners 2-C-methyl-L-lactone-1,4-lactone and 2-C-methyl-L-erythrono-1,4-lactone. (c) 2006 Published by Elsevier Ltd.
• Enantioselective synthesis of both diastereomers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated
  作者：Shū Kobayashi、Mineko Horibe、Yumi Saito

  DOI：10.1016/s0040-4020(01)85531-9

  日期：——

  Diastereo- and enantioselective synthesis of both diastereomers, including the alpha-alkoxy-beta-hydroxy-beta-methyl(phenyl) units, was performed by using chiral tin(II) Lewis acid-mediated asymmetric aldol reactions of a-alkoxy silyl enol ethers with alpha-ketoesters. (S)-1-Propyl-2-[(1,2,3,4-tetrahydroisoquinolinyl))methyl]pyrrolidine (13), a new type of chiral diamine, was found to be effective as a chiral source in these reactions and also in the reactions of 2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene (9) with aldehydes for the synthesis of optically active syn-a,p-dihydroxy thioester derivatives. (-)-2-C-Methyl-D-erythrono-1,4-lactone and (+)-2-C-methyl-L-threono-1,4-lactone were synthesized by using these reactions.
• Concise synthesis of enantiopure erythro-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate
  作者：Alexandros E. Koumbis、Apostolos D. Kaitaidis、Stefanos S. Kotoulas

  DOI：10.1016/j.tetlet.2006.09.156

  日期：2006.11

  A short and efficient approach was applied to the total synthesis of erythro-saccharinic acid lactone and the leaf-closing substance potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate from a 2-C-hydroxymethyl-D-erythrose derivative, using a combined strategy. (c) 2006 Elsevier Ltd. All rights reserved.
• An Efficient Preparation of 2-<i>C</i>-Methyl-<scp>d</scp>-Erythritol 4-Phosphoric Acid and Its Derivatives
  作者：Klaus Kis、Juraithip Wungsintaweekul、Wolfgang Eisenreich、Meinhart H. Zenk、Adelbert Bacher

  DOI：10.1021/jo9905118

  日期：2000.1.1
• WO2007/25304
  申请人：——

  公开号：——

  公开（公告）日：——