(R)-2-((tert-butoxycarbonyl)amino)-1-phenylethyl methacrylate | 1255530-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-((tert-butoxycarbonyl)amino)-1-phenylethyl methacrylate
• CAS: 1255530-26-7
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: URSXIBRHMSXWHH-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-2-((tert-butoxycarbonyl)amino)-1-phenylethyl methacrylate 、 14-Phenyltetradecan-2-one 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,5S)-3,5-dimethyl-5-(12-phenyldodecyl)dihydrofuran-2(3H)-one 、 (2S,4R)-2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone 、 rel-(2R,4R)-2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone 、 rel-(2R,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
• 作为产物：
  描述：

  甲基丙烯酸酐 、 (R)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到(R)-2-((tert-butoxycarbonyl)amino)-1-phenylethyl methacrylate
  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