(1R,4R,5S,7S,8S)-7-acetyl-5,8-dihydroxy-4-isopropyl-1-methylbicyclo[4.3.0]nonane | 457949-49-4

• 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,4R,5S,7S,8S)-7-acetyl-5,8-dihydroxy-4-isopropyl-1-methylbicyclo[4.3.0]nonane
• 英文别名: 7-Acetyl-5,8-dihydroxy-4-isopropyl-1-methylbicyclo[4.3.0]nonane, 97%；1-[(3R,3aS,5S,6S,7aR)-3a,6-dihydroxy-7a-methyl-3-propan-2-yl-2,3,4,5,6,7-hexahydro-1H-inden-5-yl]ethanone
• CAS: 457949-49-4
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: JBUVDZNSKXFWKY-QMIVOQANSA-N

物化性质

• 熔点：
  48-50 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4R,5S,7S,8S)-7-acetyl-5,8-dihydroxy-4-isopropyl-1-methylbicyclo[4.3.0]nonane 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 27.0h， 生成 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：

  胡萝卜次醇 在 臭氧 、 锌 作用下， 以 溶剂黄146 为溶剂， 以63%的产率得到(1R,4R,5S,7S,8S)-7-acetyl-5,8-dihydroxy-4-isopropyl-1-methylbicyclo[4.3.0]nonane
  参考文献：
  名称：

  Transformation of Carotol into the Hydroindane-Derived Musk Odorant

  摘要：

  Ozonolysis of carotol (1) gives dihydroxy ketone 2 (63% yield), the absolute configuration of which was established by X-ray crystallography. An acidic dehydration of 2 delivers a mixture of isomeric ketones 3 and 4 (3:1) that, catalysed by Pd/C in cyclohexene, yields a 1:1 thermodynamic mixture of 3 and 6, Ketone 6 exhibits an intensive musk odour. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200206)2002:11<1826::aid-ejoc1826>3.0.co;2-a

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.
• Transformation of Carotol into the Hydroindane-Derived Musk Odorant
  作者：Jozef Kula、Radoslaw Bonikowski、Maria Staniszewska、Arkadiusz Krakowiak、Michal W. Wieczorek、Wieslaw R. Majzner、Grzegorz D. Bujacz

  DOI：10.1002/1099-0690(200206)2002:11<1826::aid-ejoc1826>3.0.co;2-a

  日期：2002.6

  Ozonolysis of carotol (1) gives dihydroxy ketone 2 (63% yield), the absolute configuration of which was established by X-ray crystallography. An acidic dehydration of 2 delivers a mixture of isomeric ketones 3 and 4 (3:1) that, catalysed by Pd/C in cyclohexene, yields a 1:1 thermodynamic mixture of 3 and 6, Ketone 6 exhibits an intensive musk odour. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.