(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-one | 1585153-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-one
• CAS: 1585153-95-2
• 化学式: C₂₄H₃₄O₃
• 分子量: 370.532
• InChiKey: REKKETLFOAIUAZ-VERIIDFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-one 在 硼烷四氢呋喃络合物 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.08h， 以60%的产率得到
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)-Walsucochin B

  摘要：

  The first enantioselective total synthesis of the structurally unique nortriterpenoid (-)-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth-Gilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.

  DOI：

  10.1021/ol500553x
• 作为产物：
  描述：

  (S)-3-((E)-5-(2-((E)-4-(4-methoxy-2,3-dimethylphenyl)but-2-en-2-yl)-1,3-dithian-2-yl)-3-methylpent-3-en-1-yl)-2,2-dimethyloxirane 在 碘 、 calcium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以82%的产率得到(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)-Walsucochin B

  摘要：

  The first enantioselective total synthesis of the structurally unique nortriterpenoid (-)-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth-Gilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.

  DOI：

  10.1021/ol500553x