[(1S,4R,5S,6R,8R)-5-[2-(furan-3-yl)ethyl]-4,5-dimethyl-9-oxatricyclo[6.2.2.01,6]dodec-11-en-11-yl]methanol | 1119489-04-1

• 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: [(1S,4R,5S,6R,8R)-5-[2-(furan-3-yl)ethyl]-4,5-dimethyl-9-oxatricyclo[6.2.2.01,6]dodec-11-en-11-yl]methanol
• CAS: 1119489-04-1
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: JKLJPKBGUMPKGE-KATXQCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  42.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 [(1S,4R,5S,6R,8R)-5-[2-(furan-3-yl)ethyl]-4,5-dimethyl-9-oxatricyclo[6.2.2.01,6]dodec-11-en-11-yl]methanol 在 gold(III) chloride 作用下， 以61%的产率得到18-ethoxy-18,19:15,16-diepoxy-ent-clerodan-2(3),13(16),14-trien
  参考文献：
  名称：

  Microwave-assisted gold(I) catalyzed pyran ring opening in brevifloralactone: synthesis of the hawtriwaic acid core

  摘要：

  An efficient microwave-assisted Au(I) catalyzed cleavage of the pyran ring of brevifloralactone is described. We report one of the first combination reactions of gold and microwave irradiation. In base to this reaction, nine new ent-clerodane diterpene derivatives have been obtained by partial synthesis from brevi floralactone, a naturally occurring clerodane-type diterpene isolated in large quantities from the aerial part of Salvia breviflora. The clerodane diterpenes have very interesting biological activities and the semisynthetic approach described here represents an alternative to obtain them from other major diterpenes isolated from natural sources. The structures of these compounds were stablished from their physical and spectroscopic data. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.087
• 作为产物：
  描述：

  C₂₆H₄₂O₃Si 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到[(1S,4R,5S,6R,8R)-5-[2-(furan-3-yl)ethyl]-4,5-dimethyl-9-oxatricyclo[6.2.2.01,6]dodec-11-en-11-yl]methanol
  参考文献：
  名称：

  Microwave-assisted gold(I) catalyzed pyran ring opening in brevifloralactone: synthesis of the hawtriwaic acid core

  摘要：

  An efficient microwave-assisted Au(I) catalyzed cleavage of the pyran ring of brevifloralactone is described. We report one of the first combination reactions of gold and microwave irradiation. In base to this reaction, nine new ent-clerodane diterpene derivatives have been obtained by partial synthesis from brevi floralactone, a naturally occurring clerodane-type diterpene isolated in large quantities from the aerial part of Salvia breviflora. The clerodane diterpenes have very interesting biological activities and the semisynthetic approach described here represents an alternative to obtain them from other major diterpenes isolated from natural sources. The structures of these compounds were stablished from their physical and spectroscopic data. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.087

文献信息

• Microwave-assisted gold(I) catalyzed pyran ring opening in brevifloralactone: synthesis of the hawtriwaic acid core
  作者：Luis D. Miranda、Joaquín González Marrero、Elihú Bautista、Emma Maldonado、Alfredo Ortega

  DOI：10.1016/j.tetlet.2008.11.087

  日期：2009.2

  An efficient microwave-assisted Au(I) catalyzed cleavage of the pyran ring of brevifloralactone is described. We report one of the first combination reactions of gold and microwave irradiation. In base to this reaction, nine new ent-clerodane diterpene derivatives have been obtained by partial synthesis from brevi floralactone, a naturally occurring clerodane-type diterpene isolated in large quantities from the aerial part of Salvia breviflora. The clerodane diterpenes have very interesting biological activities and the semisynthetic approach described here represents an alternative to obtain them from other major diterpenes isolated from natural sources. The structures of these compounds were stablished from their physical and spectroscopic data. (C) 2008 Elsevier Ltd. All rights reserved.