1-{2,6-dihydroxy-4-methoxy-3-[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl}ethanone | 1013913-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{2,6-dihydroxy-4-methoxy-3-[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl}ethanone
• 英文别名: 1-[2,6-dihydroxy-4-methoxy-3-[(1R,6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-yl]phenyl]ethanone
• CAS: 1013913-57-9
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: BBIFXULCXOUXKX-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  1-{2,6-dihydroxy-4-methoxy-3-[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl}ethanone 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 丙酮 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (E)-1-{2-hydroxy-4-methoxy-6-methoxymethoxy-3-[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl}-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  The First Total Syntheses of (+)-Hostmanin A and (+)-Methyllinderatin

  摘要：

  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.

  DOI：

  10.3987/com-10-12084
• 作为产物：
  描述：

  1-(2,6-二羟基-4-甲氧基苯基)乙酮 、 水芹烯 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以76%的产率得到1-{2,6-dihydroxy-4-methoxy-3-[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl}ethanone
  参考文献：
  名称：

  (-)-Linderol A的短对映选择性全合成

  摘要：

  (-)-linderol A 的高效短对映选择性全合成是通过五步反应实现的，从 4-甲氧基苯乙酮开始，总产率为 30%。

  DOI：

  10.1055/s-2007-1000834

文献信息

• Improved Enantioselective Synthesis of (<b>−</b>)-Linderol A: Hindered Rotation about Aryl−Csp³ Bond
  作者：Pierre-Olivier Delaye、Pedro Lameiras、Nelly Kervarec、Catherine Mirand、Hatice Berber

  DOI：10.1021/jo902567y

  日期：2010.4.16

  phloroacetophenone and (−)-α-phellandrene, two commercially available reagents. In the diastereoselective epoxidation step, the analysis of the two endocyclic epoxide intermediates reveals a hindered sp2−sp3 rotation, which results in rotational diastereoisomers.

  从五苯乙酮和（-）-α-水芹烯（两种市售试剂）开始，通过五步反应以21％的总收率实现了对（-）-linderol A的改进的对映选择性全合成。在非对映选择性环氧化步骤中，对两种环内环氧化物中间体的分析显示出受阻的sp 2 -sp 3旋转，这导致旋转的非对映异构体。
• A Short Enantioselective Total Synthesis of (-)-Linderol A<b />
  作者：Hatice Berber、Pierre-Olivier Delaye、Catherine Mirand

  DOI：10.1055/s-2007-1000834

  日期：2008.1

  An efficient short enantioselective total synthesis of (-)-linderol A was achieved via a five-step reaction with 30% overall yield, starting from 4-methoxyphloroacetophenone.

  (-)-linderol A 的高效短对映选择性全合成是通过五步反应实现的，从 4-甲氧基苯乙酮开始，总产率为 30%。
• 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.