2-[(9R,10R)-10-(hydroxymethyl)-4,5,14,15-tetramethoxy-9-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl]propan-2-ol | 1528629-90-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苯并环辛二烯木脂素
• 英文名称: 2-[(9R,10R)-10-(hydroxymethyl)-4,5,14,15-tetramethoxy-9-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl]propan-2-ol
• CAS: 1528629-90-4
• 化学式: C₂₄H₃₂O₆
• 分子量: 416.514
• InChiKey: HQEJENRZOPDKJB-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(9R,10R)-10-(hydroxymethyl)-4,5,14,15-tetramethoxy-9-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl]propan-2-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以77%的产率得到(9R,13R)-4,5,17,18-tetramethoxy-12,12-dimethyl-11-oxatetracyclo[13.4.0.02,7.09,13]nonadeca-1(19),2,4,6,15,17-hexaen-10-one
  参考文献：
  名称：

  Synthesis of Sterically Hindered Chiral 1,4-Diols from Different Lignan-Based Backbones

  摘要：

  Methods for synthetic modifications of the natural dibenzylbutyrolactone lignan hydroxymatairesinol into chiral 1,4-diols with different lignan-derived backbones have been developed. A stepwise procedure, involving alkylation and oxidation, was shown to be successful and several highly substituted 1,4-diols were prepared. Some substituted butyrolactones resisted alkylation and led to the formation unusually stable hemiketals (butyrolactols). The formation of stable hemiketals was investigated in detail, showing that different backbone structures influence the formation and reactivity of the hemiketals.

  DOI：

  10.1055/s-0033-1340084
• 作为产物：
  描述：

  甲基溴化镁 、 (3aS^*,13aS^*;8a,8bR^*)-6,7,10,11-tetramethoxy-3a,4,13,13a-tetrahydrodibenzo<4',5':6',7'>cycloocta<1,2-c>furan-1(3H)-one 以 四氢呋喃 、 乙醚 为溶剂， 以98%的产率得到2-[(9R,10R)-10-(hydroxymethyl)-4,5,14,15-tetramethoxy-9-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl]propan-2-ol
  参考文献：
  名称：

  Synthesis of Sterically Hindered Chiral 1,4-Diols from Different Lignan-Based Backbones

  摘要：

  Methods for synthetic modifications of the natural dibenzylbutyrolactone lignan hydroxymatairesinol into chiral 1,4-diols with different lignan-derived backbones have been developed. A stepwise procedure, involving alkylation and oxidation, was shown to be successful and several highly substituted 1,4-diols were prepared. Some substituted butyrolactones resisted alkylation and led to the formation unusually stable hemiketals (butyrolactols). The formation of stable hemiketals was investigated in detail, showing that different backbone structures influence the formation and reactivity of the hemiketals.

  DOI：

  10.1055/s-0033-1340084

文献信息

• Synthesis of Sterically Hindered Chiral 1,4-Diols from Different Lignan-Based Backbones
  作者：Patrik Eklund、Yury Brusentsev、Mikko Hänninen

  DOI：10.1055/s-0033-1340084

  日期：——

  Methods for synthetic modifications of the natural dibenzylbutyrolactone lignan hydroxymatairesinol into chiral 1,4-diols with different lignan-derived backbones have been developed. A stepwise procedure, involving alkylation and oxidation, was shown to be successful and several highly substituted 1,4-diols were prepared. Some substituted butyrolactones resisted alkylation and led to the formation unusually stable hemiketals (butyrolactols). The formation of stable hemiketals was investigated in detail, showing that different backbone structures influence the formation and reactivity of the hemiketals.