5-(1-hydroxyhexyl)furan-2(5H)-one

• 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-hydroxyhexyl)furan-2(5H)-one
• 英文别名: (2S)-2-[(1S)-1-hydroxyhexyl]-2H-furan-5-one
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: DSYGVFSHAXZXIM-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲硅氧基-2-呋喃 、 正己醛 在 triethylsilyl methanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (+/-)-(5S,1'R)-5-(1'-hydroxyhexyl)-5H-furan-2-one 、 5-(1-hydroxyhexyl)furan-2(5H)-one
  参考文献：
  名称：

  2-三甲基甲硅烷氧基呋喃与醛的定向羟醛缩合中的非对映选择性。苏式和赤式δ-羟基-γ-内酯的立体发散途径

  摘要：

  通过改变反应反应条件，使2-三甲基甲硅烷氧基呋喃和醛缩合，可以得到有用的非对映体选择，得到苏-和赤--δ-羟基-α，β-不饱和γ-内酯。提出了立体力学原理，并结合了实用的两步合成苏式和赤式5-羟基-4-癸醇化物（L因子）的方法。

  DOI：

  10.1016/s0040-4039(01)83855-7

文献信息

• Diastereoselectivity in the directed aldol condensation of 2-trimethylsiloxyfuran with aldehydes. A stereodivergent route to threo and erythro δ-hydroxy-γ-lactones
  作者：Charles W. Jefford、Danielle Jaggi、John Boukouvalas

  DOI：10.1016/s0040-4039(01)83855-7

  日期：1987.1

  Threo and erythro-δ-hydroxy-α,β-unsaturated γ-lactones are obtained with useful diastereoselection by condensing 2-trimethylsiloxyfuran and aldehydes by varying the reaction reaction conditions. A stereomechanistic rationale is presented together with a practical two-step synthesis of the threo and erythro 5-hydroxy-4-decanolides (L factors).

  通过改变反应反应条件，使2-三甲基甲硅烷氧基呋喃和醛缩合，可以得到有用的非对映体选择，得到苏-和赤--δ-羟基-α，β-不饱和γ-内酯。提出了立体力学原理，并结合了实用的两步合成苏式和赤式5-羟基-4-癸醇化物（L因子）的方法。
• Synthesis of (–)-Muricatacin and (–)-(R,R)-L-Factor Involving an Organocatalytic Direct Vinylogous Aldol Reaction
  作者：Christopher Cooze、Amarender Manchoju、Sunil Pansare

  DOI：10.1055/s-0036-1590858

  日期：2017.12

  Concise syntheses of the polyketide natural product (–)-muricatacin and (–)-( R , R )-L-factor (natural product enantiomer) were achieved in four steps by employing an organocatalytic asymmetric direct vinylogous aldol reaction of γ-crotonolactone and suitable aliphatic aldehydes as the key step.

  聚酮化合物天然产物 (-)-muricatacin 和 (-)-( R , R )-L-因子（天然产物对映异构体）的简明合成是通过采用 γ-巴豆内酯和合适的脂肪醛作为关键步骤。
• 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.
• Synthesis of furanone-Based natural product analogues with quorum sensing antagonist activity
  作者：Thomas Hjelmgaard、Tobias Persson、Thomas B Rasmussen、Michael Givskov、John Nielsen

  DOI：10.1016/s0968-0896(03)00295-5

  日期：2003.7

  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.
• Silica sulfuric acid as a reusable heterogeneous catalyst for the diastereoselective Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan: facile synthesis of γ-butenolides
  作者：Gowravaram Sabitha、M. Nagendra Prasad、M. Ramesh、J. S. Yadav

  DOI：10.1007/s00706-010-0388-z

  日期：2010.11

  Silica sulfuric acid was found to be an efficient catalyst for the vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aldehydes with good diastereoselection. The reaction proceeds rapidly in THF, affording the corresponding 5-(arylhydroxymethyl) furan-2(5H)-ones in good yields. This method offers significant advantages such as experimental simplicity, and recoverability and reusability of the catalyst.