(3R,3aS,6S,6aR)-3,6-dimethyl-1-oxo-4,5,6,6a-tetrahydro-3aH-cyclopenta[c]furan-3-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,3aS,6S,6aR)-3,6-dimethyl-1-oxo-4,5,6,6a-tetrahydro-3aH-cyclopenta[c]furan-3-carbaldehyde
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: YGEBHWBUFAIGMM-OORONAJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,3aS,6S,6aR)-3,6-dimethyl-1-oxo-4,5,6,6a-tetrahydro-3aH-cyclopenta[c]furan-3-carbaldehyde 在 甲烷磺酸 、 四磷十氧化物 作用下， 反应 2.0h， 生成 dehydronepetalactone
  参考文献：
  名称：

  Photochemical Synthesis of Nepetanudone

  摘要：

  Nepetanudone and nepetaparnone have been suspected of being the products of a photochemical dimerization of nepetapyrone. Both are natural products found in a variety of Nepeta species. The synthesis of (+/-)-nepetapyrone and subsequent photochemical experiments are described. (+/-)-Nepetanudone was produced upon irradiation of (+/-)-nepetapyrone, while (+/-)-nepetaparnone, a diastereomer of nepetanudone, was not observed.

  DOI：

  10.1021/np500832h
• 作为产物：
  描述：

  4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one 在 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 (3R,3aS,6S,6aR)-3,6-dimethyl-1-oxo-4,5,6,6a-tetrahydro-3aH-cyclopenta[c]furan-3-carbaldehyde
  参考文献：
  名称：

  Photochemical Synthesis of Nepetanudone

  摘要：

  Nepetanudone and nepetaparnone have been suspected of being the products of a photochemical dimerization of nepetapyrone. Both are natural products found in a variety of Nepeta species. The synthesis of (+/-)-nepetapyrone and subsequent photochemical experiments are described. (+/-)-Nepetanudone was produced upon irradiation of (+/-)-nepetapyrone, while (+/-)-nepetaparnone, a diastereomer of nepetanudone, was not observed.

  DOI：

  10.1021/np500832h

文献信息

• Total Synthesis and Absolute Configuration of the Guaiane Sesquiterpene Englerin A
  作者：Matthieu Willot、Lea Radtke、Daniel Könning、Roland Fröhlich、Viktoria H. Gessner、Carsten Strohmann、Mathias Christmann

  DOI：10.1002/anie.200905032

  日期：2009.11.16

  ingredient of catmint, was selected as starting material for the first enantioselective synthesis of englerin A. This cytotoxic guaiane sesquiterpene is a highly selective inhibitor (1–87 nM) of several renal cancer cell lines. The absolute configuration of this natural product was determined by total synthesis.

  猫薄荷狂热：荆芥内酯的神经活性成分荆芥内酯被选作englerin A的第一个对映选择性合成的原料。这种具有细胞毒性的愈创木酚倍半萜烯是几种肾癌细胞系的高度选择性抑制剂（1-87 n M）。该天然产物的绝对构型由总合成确定。