(1R,2S,3R,6S,9S,10S,12S)-10-(hydroxymethyl)-2,6,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecane-3,12-diol | 217093-11-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,3R,6S,9S,10S,12S)-10-(hydroxymethyl)-2,6,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecane-3,12-diol
• CAS: 217093-11-3
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: GLTIPSHJVWBITP-IQGPVAMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (1R,2S,3R,6S,9S,10S,12S)-10-(hydroxymethyl)-2,6,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecane-3,12-diol 在 zinc(II) chloride 作用下， 反应 15.0h， 以55%的产率得到(1R,2S,3R,6S,9S,10S,15S)-2,6,15-trimethyl-12-phenyl-11,13,16-trioxatetracyclo[8.6.0.01,6.09,15]hexadecan-3-ol
  参考文献：
  名称：

  A general synthetic route of dihydroagarofuran sesquiterpenoid from α-(−)-santonin

  摘要：

  A general and efficient approach for synthesis of dihydroagarofuran sesquiterpenoid, the core structure of the polyol esters extensively present in the Celastraceae plants, has been developed by a series of transformations, which mainly include three creative and synthetically valuable conversions: the strategic double-bond shifting of 3, the versatile rearrangement of epoxide 5 generating two key functions, the C5-OH and 7,11-Double-bond, and the stereoselective cyclization/reduction of 8 constructing the tetrahydrofuran ring of 11. Thus the sesquiterpenoid 3 alpha,6 alpha,12-trihydroxy-dihydoagarofuran 1 was synthesized. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01766-3
• 作为产物：
  描述：

  3,3-ethylenedioxy-6α,13-dihydroxyagarofuran 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 丙酮 作用下， 以 乙醚 为溶剂， 反应 4.25h， 生成 (1R,2S,3R,6S,9S,10S,12S)-10-(hydroxymethyl)-2,6,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecane-3,12-diol
  参考文献：
  名称：

  A general synthetic route of dihydroagarofuran sesquiterpenoid from α-(−)-santonin

  摘要：

  A general and efficient approach for synthesis of dihydroagarofuran sesquiterpenoid, the core structure of the polyol esters extensively present in the Celastraceae plants, has been developed by a series of transformations, which mainly include three creative and synthetically valuable conversions: the strategic double-bond shifting of 3, the versatile rearrangement of epoxide 5 generating two key functions, the C5-OH and 7,11-Double-bond, and the stereoselective cyclization/reduction of 8 constructing the tetrahydrofuran ring of 11. Thus the sesquiterpenoid 3 alpha,6 alpha,12-trihydroxy-dihydoagarofuran 1 was synthesized. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01766-3

文献信息

• A Novel, Efficient, and Highly Selective O-Bn Bond Cleavage Reaction via a Rare K-Induced Electron Transfer Process
  作者：Yong Qiang Tu、Lei Shi、Wu Jiong Xia、Fu Min Zhang

  DOI：10.1055/s-2002-33519

  日期：——

  A new, efficient and highly selective deprotective method of both benzyl and benzylidene groups for protection of monohydroxyl and dihydroxyl, respectively, has been developed by using the system K-t-BuNH2-t-BuOH-18-crown-6. This method is valuable since it can not only selectively protect the TBDMS and THP groups and the ethylene ketal from cleavage, but also keep the separate or conjugated C=C bonds

  使用 Kt-BuNH2-t-BuOH-18-crown-6 系统开发了一种新的、高效的、高选择性的苄基和亚苄基去保护方法，分别用于保护单羟基和二羟基。这种方法很有价值，因为它不仅可以选择性地保护 TBDMS 和 THP 基团以及乙烯缩酮免于裂解，而且还可以防止单独或共轭的 C=C 键被还原。还提出了可能的电子转移反应过程。