2(5H)-Furanone, 3-hydroxy-5-((1R,2E,4E,6R,8E,10E,12S)-1-hydroxy-6,8,12-trimethyl-2,4,8,10-tetradecatetraenyl)-5-methyl-, (5R)- | 402490-28-2

• 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: 2(5H)-Furanone, 3-hydroxy-5-((1R,2E,4E,6R,8E,10E,12S)-1-hydroxy-6,8,12-trimethyl-2,4,8,10-tetradecatetraenyl)-5-methyl-, (5R)-
• 英文别名: (5R)-3-hydroxy-5-[(1R,2E,4E,6R,8E,10E,12S)-1-hydroxy-6,8,12-trimethyltetradeca-2,4,8,10-tetraenyl]-5-methylfuran-2-one
• CAS: 402490-28-2
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: WCQMJODEMARIPM-RVMDNROXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以85%的产率得到2(5H)-Furanone, 3-hydroxy-5-((1R,2E,4E,6R,8E,10E,12S)-1-hydroxy-6,8,12-trimethyl-2,4,8,10-tetradecatetraenyl)-5-methyl-, (5R)-
  参考文献：
  名称：

  The total synthesis and biological evaluation of nafuredin-γ and its analogues

  摘要：

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.066

文献信息

• The total synthesis and biological evaluation of nafuredin-γ and its analogues
  作者：Tohru Nagamitsu、Daisuke Takano、Miyuki Seki、Shiho Arima、Masaki Ohtawa、Kazuro Shiomi、Yoshihiro Harigaya、Satoshi Ōmura

  DOI：10.1016/j.tet.2008.06.066

  日期：2008.8

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.