3,4-bis(benzyloxy)-5-(2-hydroxyethyl)furan-2(5H)-one | 185675-41-6

• 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: 3,4-bis(benzyloxy)-5-(2-hydroxyethyl)furan-2(5H)-one
• 英文别名: 3,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanone；2-(2-hydroxyethyl)-3,4-bis(phenylmethoxy)-2H-furan-5-one
• CAS: 185675-41-6
• 化学式: C₂₀H₂₀O₅
• 分子量: 340.376
• InChiKey: XIVOGTRQHQBSPK-UHFFFAOYSA-N

物化性质

• 沸点：
  627.0±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-bis(benzyloxy)-5-(2-hydroxyethyl)furan-2(5H)-one 、 棕榈酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2-(3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)ethyl palmitate
  参考文献：
  名称：

  ASCORBIC ACID-RELATED COMPOUND AND ANTI-PLANT-VIRUS AGENT

  摘要：

  本发明提供一种由式（1）表示的化合物（其中X1和X2中的每一个独立表示-OR1、-NR2R3或-CR4R5R6等，R1、R2、R3、R4、R5和R6中的每一个独立表示未取代或取代基团的糖基或未取代或取代基团的C1至C30烷基基团等，A表示未取代或取代基团的C1至C30烷基基团等）或其盐。

  公开号：

  EP2902387A1
• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3,4-bis(benzyloxy)-5-(2-hydroxyethyl)furan-2(5H)-one
  参考文献：
  名称：

  ASCORBIC ACID-RELATED COMPOUND AND ANTI-PLANT-VIRUS AGENT

  摘要：

  本发明提供一种由式（1）表示的化合物（其中X1和X2中的每一个独立表示-OR1、-NR2R3或-CR4R5R6等，R1、R2、R3、R4、R5和R6中的每一个独立表示未取代或取代基团的糖基或未取代或取代基团的C1至C30烷基基团等，A表示未取代或取代基团的C1至C30烷基基团等）或其盐。

  公开号：

  EP2902387A1

文献信息

• 5,5-Disubstituted-3, 4-dihydroxy-2(5H)-furanones and methods of use
  申请人：Oxis International, Inc.

  公开号：US06005000A1

  公开（公告）日：1999-12-21

  The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.

  本发明涉及用于合成旋光活性和消旋5,5-二取代-3,4-二羟基-2(5H)-呋喃酮；5-[(4-芳基)-3-丁炔基]-3,4-二羟基-2(5H)-呋喃酮；5-(2-芳硫基)乙基-3,4-二羟基-2(5H)-呋喃酮；以及5-(2-芳氧基)乙基-3,4-二羟基-2(5H)-呋喃酮的生产的合成方法。本发明进一步涉及上述化合物作为抗炎药物的用途，通过它们作为脂质过氧化、5-脂氧合酶、环氧合酶-1和环氧合酶-2的混合抑制剂的作用。该发明还涉及将这些化合物用于治疗慢性炎症性疾病，如哮喘、类风湿性关节炎、炎症性肠病、动脉粥样硬化、急性呼吸窘迫综合征，以及阿尔茨海默病和帕金森病等中枢神经系统疾病，其中活性氧自由基和炎症介质是造成有害因素的。
• Organoalane-mediated isomerization of ascorbic and isoascorbic acid derivatives
  作者：Josef Schachtner、Hans-Dietrich Stachel

  DOI：10.1016/0957-4166(96)00427-2

  日期：1996.11

  removal of the protecting groups is effected by hydrogenolysis of the benzylidene acetals ent-10 and ent-11a. This reaction leads to d-ascorbic acid ent-1a or l-isoascorbic acid ent-1b, respectively. Furthermore, the four acetonides 2 were converted by ozonolysis, transesterification and finally catalytic hydrogenation to the threonic and erythronic acid ketals 9.

  当用三异丁基铝处理时，l-抗坏血酸2a和d-异抗坏血酸2b的衍生物部分发生差向异构化，生成l-异抗坏血酸ent - 2b，ent -10b或d-抗坏血酸ent - 2a ，ent -11a分别。保护基的完全除去是通过对亚甲基缩醛ent -10和ent- 11a进行氢解来实现的。该反应导致d抗坏血酸ENT -1a或1-异抗坏血酸ENT分别-1b。此外，四种丙酮化物2被臭氧分解，酯交换，最后催化氢化转化为苏糖醛和赤藓酸缩酮9。
• Pharmaceutical methods of use of 5-substituted and 5,5 disubstituted-3,4-dihydroxy-2(5H)-furanones
  申请人：Oxis International Inc.

  公开号：US06262073B1

  公开（公告）日：2001-07-17

  The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.

  本发明涉及合成方法，用于生产旋光和消旋5,5-二取代-3,4-二羟基-2（5H）-呋喃酮；5-[(4-芳基)-3-丁炔基]-3,4-二羟基-2（5H）-呋喃酮；5-（2-芳硫基）乙基-3,4-二羟基-2（5H）-呋喃酮；以及5-（2-芳氧基）乙基-3,4-二羟基-2（5H）-呋喃酮。本发明进一步涉及上述化合物的用途，作为抗炎剂，通过它们作为脂质过氧化、5-脂氧合酶、环氧化酶-1和环氧化酶-2的混合抑制剂的作用。本发明进一步涉及在治疗慢性炎症性疾病，如哮喘、类风湿性关节炎、炎症性肠病、动脉粥样硬化、急性呼吸窘迫综合征和中枢神经系统疾病，如阿尔茨海默病和帕金森病中使用这些化合物，其中活性氧物质和炎症介质是造成有害因素的贡献者。
• 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones and methods of use
  申请人：Oxis International Inc.

  公开号：US06136832A1

  公开（公告）日：2000-10-24

  The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.

  本发明涉及合成方法，用于生产旋光和消旋5,5-二取代-3,4-二羟基-2（5H）-呋喃酮；5-[(4-芳基)-3-丁炔基]-3,4-二羟基-2（5H）-呋喃酮；5-（2-芳硫基）乙基-3,4-二羟基-2（5H）-呋喃酮；以及5-（2-芳氧基）乙基-3,4-二羟基-2（5H）-呋喃酮。本发明还涉及上述化合物作为抗炎药物的用途，通过它们作为脂质过氧化、5-脂氧合酶、环氧合酶-1和环氧合酶-2的混合抑制剂的作用。本发明还涉及在治疗慢性炎症性疾病，如哮喘、类风湿性关节炎、炎症性肠病、动脉粥样硬化、急性呼吸窘迫综合征以及中枢神经系统疾病，如阿尔茨海默病和帕金森病等，其中活性氧和炎症介质是致病因素的情况下使用这些化合物的用途。
• ASCORBIC ACID-RELATED COMPOUND AND PLANT ANTIVIRAL AGENT
  申请人：NIPPON SODA CO., LTD.

  公开号：US20150250169A1

  公开（公告）日：2015-09-10

  The present invention provides a compound represented by formula (1) (wherein each of X 1 and X 2 independently represents —OR 1 , —NR 2 R 3 or —CR 4 R 5 R 6 or the like, each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 independently represents an unsubstituted or substituent-bearing glycosyl group or an unsubstituted or substituent-bearing C1 to C30 alkyl group or the like, and A represents an unsubstituted or substituent-bearing C1 to C30 alkyl group or the like) or a salt thereof.

  本发明提供一种由式（1）表示的化合物（其中X1和X2分别独立表示—OR1，—NR2R3或—CR4R5R6或类似物，R1、R2、R3、R4、R5和R6分别独立表示未取代或取代基的糖基或未取代或取代基的C1到C30烷基或类似物，A表示未取代或取代基的C1到C30烷基或类似物）或其盐。