3-(1-hydroxyoctyl)-5-methylfuran-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: 3-(1-hydroxyoctyl)-5-methylfuran-2(5H)-one
• 英文别名: rac-acaterin；(±)-acaterin；Acaterin；4-(1-hydroxyoctyl)-2-methyl-2H-furan-5-one
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: YUMHJXLSSASJGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  4,5-dihydro-5-methyl-3-(phenylthio)furan-2(3H)-one 在 正丁基锂 、 二异丙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 3-(1-hydroxyoctyl)-5-methylfuran-2(5H)-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

文献信息

• Synthesis of acaterin via a new application of the Baylis–Hillman reaction
  作者：Xavier Franck、Bruno Figadère

  DOI：10.1016/s0040-4039(02)00058-8

  日期：2002.2

  Acaterin 1 was synthesized by condensation of a chiral α,β-unsaturated γ-lactone with octanal via a DABCO-mediated Baylis–Hillman reaction. This is the first application of the Baylis–Hillman reaction to α,β-unsaturated lactones.

  通过DABCO介导的Baylis-Hillman反应，将手性α，β-不饱和γ-内酯与辛醛缩合，合成了Acaterin 1。这是Baylis-Hillman反应对α，β-不饱和内酯的首次应用。
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Metallic chalcogenolates mediated modular Michael-aldol cascade reaction: an easy route to multi-functionalized chalcogenides and Morita–Baylis–Hillman adducts
  作者：Bruno A. Sousa、Arthur F. Keppler、Rogério A. Gariani、João V. Comasseto、Alcindo A. Dos Santos

  DOI：10.1016/j.tet.2012.09.027

  日期：2012.12

  Chalcogenolate mediated Michael-aldol cascade reactions consists of a very efficient route to multi-functionalized gamma-hydroxichalcogenides. Although, when selenolates are employed, these gamma-hydroxichalcogenides can be readily converted into the corresponding Morita-Baylis-Hillman adducts by oxidative elimination of the selenium moiety. In this context, herein we present a complete study on the scope and limitations of this reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• PROCESSES AND HOST CELLS FOR GENOME, PATHWAY, AND BIOMOLECULAR ENGINEERING
  申请人：enEvolv, Inc.

  公开号：EP3027754A1

  公开（公告）日：2016-06-08
• TREATMENT FOR SOLID TUMORS
  申请人：White David William

  公开号：US20090192220A1

  公开（公告）日：2009-07-30

  A method for treating a solid tumor in a subject comprises administering to the subject an ACAT inhibitory compound or a prodrug thereof, for example avasimibe, wherein (a) the solid tumor is at least about 2 mm in diameter and (b) the compound or prodrug thereof is administered in an amount that is therapeutically effective, but ineffective to cause unacceptable toxicity to normoxic tissues.

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