(+)-methyllinderatin | 120948-03-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (+)-methyllinderatin
• 英文别名: Methyllinderatin；1-[2,6-dihydroxy-4-methoxy-3-[(1R,6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-yl]phenyl]-3-phenylpropan-1-one
• CAS: 120948-03-0
• 化学式: C₂₆H₃₂O₄
• 分子量: 408.538
• InChiKey: OJZQYJGQIQVZMQ-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-methyllinderatin 在 sodium carbonate 、 Oxone 作用下， 以 丙酮 、 水 为溶剂， 反应 0.17h， 以79%的产率得到1-((5aR,6R,9R,9aS)-3,6-dihydroxy-9-isopropyl-1-methoxy-6-methyl-5a,6,7,8,9,9a-hexahydrodibenzo[b,d]furan-4-yl)-3-phenylpropan-1-one
  参考文献：
  名称：

  Enantioselective Total Syntheses of (+)-Hostmanin A, (−)-Linderol A, (+)-Methyllinderatin and Structural Reassignment of Adunctin E

  摘要：

  A one-step protocol has been developed for the enantioselective synthesis of hexahydrodibenzofuran derivatives using a modified Friedel-Crafts reaction. The developed method was applied to the synthesis of a series of natural products including (+)-hostmanin A, (+)-methyllinderatin, and (-)-linderol A. The synthetic and spectroscopic data investigations led to the structural. reassignment of natural product adunctin E, which was further confirmed by single-crystal X-ray analysis.

  DOI：

  10.1021/acs.joc.5b00331
• 作为产物：
  描述：

  1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-2-propen-1-one 在 5%-palladium/activated carbon 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.25h， 生成 (+)-methyllinderatin
  参考文献：
  名称：

  Enantioselective Total Syntheses of (+)-Hostmanin A, (−)-Linderol A, (+)-Methyllinderatin and Structural Reassignment of Adunctin E

  摘要：

  A one-step protocol has been developed for the enantioselective synthesis of hexahydrodibenzofuran derivatives using a modified Friedel-Crafts reaction. The developed method was applied to the synthesis of a series of natural products including (+)-hostmanin A, (+)-methyllinderatin, and (-)-linderol A. The synthetic and spectroscopic data investigations led to the structural. reassignment of natural product adunctin E, which was further confirmed by single-crystal X-ray analysis.

  DOI：

  10.1021/acs.joc.5b00331

文献信息

• The First Total Syntheses of (+)-Hostmanin A and (+)-Methyllinderatin
  作者：Masayuki Yamashita、Junko Kitao、Naoko Kitamura、Nozomi Kumo、Ai Kurume、Kenji Arimitsu、Hiroki Iwasaki、Minoru Ozeki

  DOI：10.3987/com-10-12084

  日期：——

  The first total syntheses of (+)-hostmanin A (1) and (+)-methyllinderatin (3) were achieved in four steps from a known compound, 1-2,6-dihydroxy-4-methoxy-3-[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl}ethanone (6). The absolute configuration of (+)-methyllinderatin (3) was determined. Furthermore, (+)-hostmanin A (1), which was isolated as an inseparable mixture of hostmanin A and B, was synthesized as a sole component.