(5S)-5-isopropyl-2(5H)-furanone | 98878-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5S)-5-isopropyl-2(5H)-furanone
• 英文别名: (R)-isopropyl butenolide；(S)-5-isopropylfuran-2(5H)-one；5-isopropyl-2(5H)-furanone；(2S)-2-propan-2-yl-2H-furan-5-one
• CAS: 98878-24-1
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: LWFKYUIZWLTJCA-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-5-isopropyl-2(5H)-furanone 在 二苯甲酮 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 methyl (1R,3S)-2,2-dimethyl-3-[(1S)-2-methyl-1-(4-methylphenoxy)carbothioyloxypropyl]cyclopropane-1-carboxylate
  参考文献：
  名称：

  Franck-Neumann, Michel; Sedrati, Madjid; Vigneron, Jean-Paul, Angewandte Chemie, 1985, vol. 97, # 11, p. 995 - 996

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-5-methyl-3-hexenoic acid 在 (S)-tert-butyl((6-methoxy-7-((4-methoxybenzyl)selanyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)oxy)dimethylsilane 、 N-氟代双苯磺酰胺 、 calcium carbonate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以99%的产率得到(5S)-5-isopropyl-2(5H)-furanone
  参考文献：
  名称：

  用于高度对映选择性氧化环化的手性亲电硒催化剂

  摘要：

  在过去的二十年中，手性亲电硒催化剂已被应用于催化烯烃的不对称转化。然而，尚未开发出具有广泛底物范围的高度对映选择性反应。我们报告了该反应的第一个成功例子，该反应采用基于刚性茚满醇支架的催化剂，该支架可以很容易地从市售茚满酮合成。该反应在温和条件下有效地将 β,γ-不饱和羧酸转化为各种对映体富集的 γ-丁烯内酯。

  DOI：

  10.1021/jacs.6b01462

文献信息

• Pd-catalyzed 5-endo-trig-type cyclization of β,γ-unsaturated carbonyl compounds: an efficient ring closing reaction to give γ-butenolides and 3-pyrrolin-2-ones
  作者：Gan B. Bajracharya、Priti S. Koranne、Rashid N. Nadaf、Randa Kassem Mohamed Gabr、Kazuhiro Takenaka、Shinobu Takizawa、Hiroaki Sasai

  DOI：10.1039/c0cc02352c

  日期：——

  The 5-endo-trig-type cyclization has been performed using a Pd-bis(isoxazoline) catalyst. The present cyclization of beta,gamma-unsaturated carbonyl compounds gave gamma-butenolides and 3-pyrrolin-2-ones in good to excellent yields.

  已经使用Pd-双（异恶唑啉）催化剂进行了5-内-trig-型环化。β，γ-不饱和羰基化合物的当前环化以良好至优异的产率得到γ-丁烯内酯和3-吡咯啉-2-酮。
• A convergent asymmetric synthesis of γ-butenolides
  作者：Marc Renard、Léon A. Ghosez

  DOI：10.1016/s0040-4020(01)00078-3

  日期：2001.3

  The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded gamma -butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of gamma -butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Kinetic resolution in Diels-Alder processes
  作者：Bernd Wegener、Martin Hansen、Ekkehard Winterfeldt

  DOI：10.1016/s0957-4166(00)86079-6

  日期：1993.3

  Examples of highly efficient kinetic resolutions with the bicyclic chiral cyclopentadiene 1 and several selected cyclic dienophiles are reported. In combination with a thermal retro-Diels-Alder process this procedure provides easy access to both enantiomers of these dienophiles.
• Pure enantiomers from retro-diels-alder processes
  作者：Marion Beckmann、Hinrich Hildebrandt、Ekkehard Winterfeldt

  DOI：10.1016/s0957-4166(00)86325-9

  日期：1990.1
• 1,3-DIHYDROXY SUBSTITUTED PHENYLAMIDE GLUCOKINASE ACTIVATORS
  申请人：Chen Sean

  公开号：US20100179121A1

  公开（公告）日：2010-07-15

  Compounds are provided which are glucokinase activators and thus are useful in treating diabetes and related diseases and have the structure wherein in the ring represents one or two double bonds; R 1 is alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl; R 2 is alkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl; R 5 is as defined herein; Z is O, S, S(O), S(O)2, or NR 5a ; X is S, O, N, NR 3 , or CR 3 ; Y is NCR 4 or NR 4 ; R 3 , R 4 , and R 5 are as defined herein; R 8 is aryl, heteroaryl, —PO(OR 9 )(OR 10 ), —PO(OR 9 )R 10 or —P(O)(R 9 )R 10 (wherein R 9 and R 10 are as defined herein)/R 6 and R 7 are independently H, halogen, or alkyl; m is 0 or 1; and n is 0 to 3, or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related diseases employing the above compounds is also provided.