1-((1aS,5aR,6aR)-3-isopropyl-5a-methyl-2,4,5,5a,6,6a-hexahydro-1-oxa-cyclopropa[f]inden-1a-yl)-ethanone | 1397290-96-8

• 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: 1-((1aS,5aR,6aR)-3-isopropyl-5a-methyl-2,4,5,5a,6,6a-hexahydro-1-oxa-cyclopropa[f]inden-1a-yl)-ethanone
• 英文别名: 1-[(1aS,5aR,6aR)-5a-methyl-3-propan-2-yl-4,5,6,6a-tetrahydro-2H-indeno[5,6-b]oxiren-1a-yl]ethanone
• CAS: 1397290-96-8
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: BYUCGFZSCVORBU-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲酸 、 1-((1aS,5aR,6aR)-3-isopropyl-5a-methyl-2,4,5,5a,6,6a-hexahydro-1-oxa-cyclopropa[f]inden-1a-yl)-ethanone 反应 36.0h， 以81%的产率得到formic acid (5R,6R,7aR)-5-acetyl-6-hydroxy-3-isopropyl-7a-methyl-2,4,5,6,7,7a-hexahydro-1H-inden-5-yl ester
  参考文献：
  名称：

  Hydroindene-derived chiral synthons from carotol and their cytotoxicity

  摘要：

  Ten enantiomerically pure hydroindene-derived compounds obtained by the transformation of (+)-carotol, the main constituent of carrot seed essential oil, were examined for their ability to inhibit the growth of myeloid leukaemia (HL-60) cancer cell lines. All compounds showed significant activity, which was comparable to the most active volatile organic compounds, such as trans-trans-farnesol, citral and nerolidol. Based on the bioactivity and molecular modelling, a 3D QSAR pharmacophore model was generated. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.005
• 作为产物：
  描述：

  1-((3R,3aS,5S,6R,7aR)-5,6-epoxy-3a-hydroxy-3-isopropyl-7a-methyl-octahydro-inden-5-yl)-ethanone 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到1-((1aS,5aR,6aR)-3-isopropyl-5a-methyl-2,4,5,5a,6,6a-hexahydro-1-oxa-cyclopropa[f]inden-1a-yl)-ethanone
  参考文献：
  名称：

  Hydroindene-derived chiral synthons from carotol and their cytotoxicity

  摘要：

  Ten enantiomerically pure hydroindene-derived compounds obtained by the transformation of (+)-carotol, the main constituent of carrot seed essential oil, were examined for their ability to inhibit the growth of myeloid leukaemia (HL-60) cancer cell lines. All compounds showed significant activity, which was comparable to the most active volatile organic compounds, such as trans-trans-farnesol, citral and nerolidol. Based on the bioactivity and molecular modelling, a 3D QSAR pharmacophore model was generated. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.005

文献信息

• Hydroindene-derived chiral synthons from carotol and their cytotoxicity
  作者：Radosław Bonikowski、Józef Kula、Anna Bujacz、Anna Wajs-Bonikowska、Małgorzata Zakłos-Szyda、Stanisław Wysocki

  DOI：10.1016/j.tetasy.2012.07.005

  日期：2012.7

  Ten enantiomerically pure hydroindene-derived compounds obtained by the transformation of (+)-carotol, the main constituent of carrot seed essential oil, were examined for their ability to inhibit the growth of myeloid leukaemia (HL-60) cancer cell lines. All compounds showed significant activity, which was comparable to the most active volatile organic compounds, such as trans-trans-farnesol, citral and nerolidol. Based on the bioactivity and molecular modelling, a 3D QSAR pharmacophore model was generated. (c) 2012 Elsevier Ltd. All rights reserved.