5-(1'-hydroxyoctyl)-5H-furan-2-one | 80314-53-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(1'-hydroxyoctyl)-5H-furan-2-one
• 英文别名: 5-(1-hydroxyoctyl)furan-2(5H)-one；5-(1-hydroxyoctyl)-2(5H)-furanone；2-(1-hydroxyoctyl)-2H-furan-5-one
• CAS: 80314-53-0
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: BVOXWQDRWQXIGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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-(1'-hydroxyoctyl)-5H-furan-2-one 在 4-二甲氨基吡啶 、 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-((Z)-octylidene)-5H-furan-2-one 、
  参考文献：
  名称：

  Synthesis of furanone-Based natural product analogues with quorum sensing antagonist activity

  摘要：

  The synthesis of 5- and 3-(1'-hydroxyalkyl)-substituted 5H-furan-2-ones 4a-d and 8a-d as well as 5-alkylidene-5H-furan-2-ones 5a-d is described. A study of the structure-activity relationship of these furanone-based natural product analogues towards two different quorum sensing systems is reported. Although the synthesized compounds are not as potent quorum sensing inhibitors as some natural counterparts and a synthetic analogue hereof, interesting structure-activity relationships are seen. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00295-5
• 作为产物：
  描述：

  三甲硅氧基-2-呋喃 、 正辛醛 在 Cr(II)(salen) 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 24.0h， 以70%的产率得到5-(1'-hydroxyoctyl)-5H-furan-2-one
  参考文献：
  名称：

  Enantioselective Addition of 2-(Trimethylsilyloxy)furan to Aldehydes Using Cr(salen) as Catalyst. Effect of Water on Enantioselectivity

  摘要：

  研究发现，阳离子 (R,R)-Cr(salen) 复合物 2 可催化 2-(三甲基硅氧基)呋喃与醛的对映选择性加成，生成 5-取代的丁烯内酯，但非对映选择性不高。少量水的存在对实现高对映体选择性至关重要。

  DOI：

  10.1246/cl.2003.584

文献信息

• Facile synthesis of 4-substituted butenolides from furan
  作者：Tatsuya Shono、Yoshihiro Matsumura、Shin-ichiro Yamane

  DOI：10.1016/s0040-4039(01)81881-5

  日期：1981.1

  A variety of 4-substituted butenolides were prepared utilizing 2-acetoxyfuran as a key intermediate which can be easily synthesized by anodic oxidation of furan.

  利用2-乙酰氧基呋喃作为关键中间体制备了多种4-取代的丁烯内酯，这些中间体很容易通过呋喃的阳极氧化而合成。
• Asymmetric Vinylogous Aldol Reaction of Silyloxy Furans with a Chiral Organic Salt
  作者：Ravi P. Singh、Bruce M. Foxman、Li Deng

  DOI：10.1021/ja103331t

  日期：2010.7.21

  significance there is a general lack of asymmetric vinylogous aldol reactions that tolerate variations of both the silyloxy furans and aldehydes. We have developed a new chiral organic catalyst based on a carboxylate-ammonium salt prepared from a thiourea-amine and a carboxylic acid. This new catalyst enabled us to develop an efficient asymmetric vinylogous aldol reaction of unprecedented scope with respect

  尽管它们具有合成意义，但普遍缺乏耐受甲硅烷氧基呋喃和醛变化的不对称乙烯基醛醇反应。我们开发了一种基于由硫脲胺和羧酸制备的羧酸铵盐的新型手性有机催化剂。这种新催化剂使我们能够针对 2-三甲基甲硅烷氧基呋喃和醛，开发出范围空前的高效不对称乙烯基醛醇反应。
• Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues
  作者：A Cavé、C Chaboche、B Figadère、J.C. Harmange、A Laurens、J.F. Peyrat、M Pichon、M Szlosek、J Cotte-Lafitte、A.M. Quéro

  DOI：10.1016/s0223-5234(97)83287-4

  日期：1997.7

  A study of the structure-cytotoxic activity of the acetogenin of Annonaceae, muricatacin 1, is reported. Indeed, muricatacin 1 has shown promising antitumoral activity. Therefore several 5-hydroxy-4-alkanolides were prepared and then tested against KB and VERO cell lines. A few other analogues were synthesized and tested against both cell lines. Thus this work allowed us to better determine the pharmacophore of the molecule and to propose muricatacin 1 instead of a more complicated acetogenin of Annonaceae as a lead compound in the search for new antineoplastic agents.
• The first organocatalytic addition of 2-trimethylsilyloxyfuran to carbonyl compounds: hydrogen-bond catalysis in γ-butenolides synthesis
  作者：Margherita De Rosa、Lucia Citro、Annunziata Soriente

  DOI：10.1016/j.tetlet.2006.09.143

  日期：2006.11

  This letter describes the first example of diastereoselective 'organocatalyzed' synthesis of the butenolide products substituted at the gamma-position by a chain bearing hydroxyl groups. The urea-derivative 4 has proved to be an efficient catalyst for the addition of the commercial TMSOF to carbonyl compounds under solvent-free conditions. The reaction conditions and generality of the procedure have been examined. (c) 2006 Elsevier Ltd. All rights reserved.
• SHONO, TATSUYA;MATSUMURA, YOSHIHIRO;YAMANE, SHIN-ICHIRO, TETRAHEDRON LETT., 1981, 22, N 34, 3269-3272
  作者：SHONO, TATSUYA、MATSUMURA, YOSHIHIRO、YAMANE, SHIN-ICHIRO

  DOI：——

  日期：——