(3S,4R,5S,6S,1E)-5-methoxy-4,6-dimethyl-1-phenyloct-1-en-7-yn-3-ol | 1210422-70-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (3S,4R,5S,6S,1E)-5-methoxy-4,6-dimethyl-1-phenyloct-1-en-7-yn-3-ol
• 英文别名: (E,3S,4R,5S,6S)-5-methoxy-4,6-dimethyl-1-phenyloct-1-en-7-yn-3-ol
• CAS: 1210422-70-0
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: FRZDVRZDPAOPDL-GSOBBUSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6S,1E)-5-methoxy-4,6-dimethyl-1-phenyloct-1-en-7-yn-3-ol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以94%的产率得到((3S,4R,5S,6S,E)-3,5-Dimethoxy-4,6-dimethyloct-1-en-7-yn-1-yl)benzene
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin C Using Hidden Symmetry

  摘要：

  A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ce >98%).

  DOI：

  10.1021/jo902582w
• 作为产物：
  描述：

  (2S,3R,4R,5S,6S,7E)-2-(chloromethyl)-4-methoxy-3,5-dimethyl-6-styryltetrahydro-2H-pyran 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(3S,4R,5S,6S,1E)-5-methoxy-4,6-dimethyl-1-phenyloct-1-en-7-yn-3-ol
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin C Using Hidden Symmetry

  摘要：

  A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ce >98%).

  DOI：

  10.1021/jo902582w

文献信息

• Total Synthesis of (+)-Crocacin C Using Hidden Symmetry
  作者：Mathieu Candy、Gérard Audran、Hugues Bienaymé、Cyril Bressy、Jean-Marc Pons

  DOI：10.1021/jo902582w

  日期：2010.3.5

  A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ce >98%).