5-hydroxy-4-tridecyl-2(5H)-furanone | 130163-18-7

• 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: 5-hydroxy-4-tridecyl-2(5H)-furanone
• 英文别名: (+/-)-5-hydroxy-4-tridecyl-5H-furan-2-one；(+/-)-5-Hydroxy-4-tridecyl-5H-furan-2-on；4-tridecyl-5-hydroxy-2(5H)-furanone；2-hydroxy-3-tridecyl-2H-furan-5-one
• CAS: 130163-18-7
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: WAQAOSBHIFXXRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4-tridecyl-2(5H)-furanone 在 sodium borohydrid 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-tridecyl-2(5H)-furanone
  参考文献：
  名称：

  Anti-inflammatory 2-furanones

  摘要：

  新的2-呋喃酮化合物具有钙通道拮抗活性，可用作抗炎药物，并用于治疗牛皮癣。

  公开号：

  US05045564A1
• 作为产物：
  描述：

  3-糠醛 在 Lindlar's catalyst 、 rose bengal 水 、 氢气 、 氧气 、 双(三甲基硅烷基)氨基钾 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 15.33h， 生成 5-hydroxy-4-tridecyl-2(5H)-furanone
  参考文献：
  名称：

  Singlet oxygen oxidation of substituted furans to 5-hydroxy-2(5H)-furanone

  摘要：

  The conditions for the regiospecific singlet oxygen oxidation of various 2,4-disubstituted furans 9 to 4-substituted-2 (5H)-furanones 3 are developed. The presence of a C-2 substituent (e.g., trimethylsilyl, tert-butyldimethylsilyl, or tributylstannyl) in 9 is an absolute requirement for the formation of the 4-substituted-5-hydroxy-2(5H)-furanone regioisomer 3. When the C-2 substituent is triethylsilyl (TES) or TBDMS, however, apart from 3, the corresponding 5-trialkylsiloxy derivative 11 is also isolated in a significant amount. These silyl acetals are unexpectedly stable but can be hydrolyzed back to 3 on stirring with dilute acid. The formation of silyl acetals, to our knowledge, has never been reported in the singlet oxygen oxidation of (trialkylsilyl)furan. A plausible mechanism for their formation is proposed. The presence of a catalytic amount of water in the oxidation of 2-(trialkylsilyl)-4-substituted-furans not only eliminates the formation of the silyl acetals but also speeds up the rate of the oxidation process. Moreover, the oxidation can then be carried out at 0-degrees-C instead of at -78-degrees-C. Oxidation of 2-(1-hydroxyalkyl)-4-substituted-furans in the absence of a reducing agent gives little or no sign of 2,5-disubstituted-6-hydroxy-3(2H)-pyranone 23 but instead 26 selectively. Thus, the (1-hydroxy)alkyl group can be utilized as the trialkylsilyl or trialkylstannyl group in dictating the regioselectivity in the singlet oxygen oxidation of substituted furans.

  DOI：

  10.1021/jo00025a012

文献信息

• Process of using anti-inflammatory furanones as selective calcium
  申请人：Allergan, Inc.

  公开号：US05376676A1

  公开（公告）日：1994-12-27

  4-(C.sub.10 -C.sub.20)alkyl-2(5H)-furanone compounds are selective calcium channel inhibitors and useful for treatment of diseases such as hypertension, angina, cardiac arrythmia, pulmonary hypertension, aortic insufficiency, Raynand's disease, migraine headaches, deficiency of platelet function, atherosclerosis, ischemia, reprofusion injury, bronchial asthma, esophageal spasm, dysmenorhea, allergic contact dermatitis, acute inflammatory response, glaucoma and as potentiators of chemotherapeutic agents in the treatment of tumors.

  4-(C.sub.10 -C.sub.20)烷基-2(5H)-呋喃酮类化合物是选择性钙通道抑制剂，可用于治疗高血压、心绞痛、心律失常、肺动脉高压、主动脉瓣不全、雷诺病、偏头痛、血小板功能缺陷、动脉粥样硬化、缺血、再灌注损伤、支气管哮喘、食管痉挛、痛经、过敏性接触性皮炎、急性炎症反应、青光眼，并在肿瘤治疗中作为化疗药物的增效剂。
• New Compounds. The γ-Lactone of 3-Tridecyl-4-hydroxy-2-butenoic Acid
  作者：David Schlichting、Glenn Jenkins

  DOI：10.1021/ja01141a601

  日期：1952.11
• US5045564A
  申请人：——

  公开号：US5045564A

  公开（公告）日：1991-09-03
• US5376676A
  申请人：——

  公开号：US5376676A

  公开（公告）日：1994-12-27
• Anti-inflammatory 2-furanones
  申请人：Allergan, Inc.

  公开号：US05045564A1

  公开（公告）日：1991-09-03

  New 2-furanone compounds have calcium channel antagonist activity and are useful as anti-inflammatory agents and in treating psoriasis.

  新的2-呋喃酮化合物具有钙通道拮抗活性，可用作抗炎药物，并用于治疗牛皮癣。