(2S,4R)-2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone | 1064016-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,4R)-2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone
• 英文别名: (3S,5R)-3,5-dimethyl-5-(12-phenyldodecyl)dihydrofuran-2(3H)-one；(3S,5R)-3,5-dimethyl-5-(12-phenyldodecyl)oxolan-2-one
• CAS: 1064016-68-7
• 化学式: C₂₄H₃₈O₂
• 分子量: 358.565
• InChiKey: FAIZHPBXQAJJPL-XUZZJYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲基丙烯酸甲酯 、 14-Phenyltetradecan-2-one 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 生成 rel-(2R,4R)-2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone 、 (2S,4R)-2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone
  参考文献：
  名称：

  A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone and its PPAR activities

  摘要：

  A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the alpha,gamma dialkyl gamma-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC(50) values of 12 mu M for mPPAR alpha, 9 mu M for mPPAR delta and > 100 mu M for mPPAR gamma. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.069

文献信息

• CHEMICAL AND BIOLOGICAL AGENTS FOR THE CONTROL OF MOLLUSCS
  申请人：Marrone Bio Innovations, Inc.

  公开号：US20130121978A1

  公开（公告）日：2013-05-16

  Compositions and methods for controlling molluscs, members of the Gastropoda and Bivalvia classes which includes but is not limited to lactones, lactams, carbamates, amides, and/or carboxylic acid containing compounds as active ingredients and/or compounds derived from Pseudomonas and/or Erwinia . Also provided are methods and compositions for increasing the efficacy of chemical and biological control for invasive molluscs in open waters, power plants, and drinking water treatment facilities under coldwater conditions.
• US8968723B2
  申请人：——

  公开号：US8968723B2

  公开（公告）日：2015-03-03
• A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone and its PPAR activities
  作者：Jaeyoung Ko、Hoosang Hwang、Jungwook Chin、Dongyup Hahn、Jaehwan Lee、Inho Yang、Kyoungjin Shin、Jungyeob Ham、Heonjoong Kang

  DOI：10.1016/j.bmcl.2010.08.069

  日期：2010.10

  A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the alpha,gamma dialkyl gamma-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC(50) values of 12 mu M for mPPAR alpha, 9 mu M for mPPAR delta and > 100 mu M for mPPAR gamma. (c) 2010 Elsevier Ltd. All rights reserved.