8α-hydroxyachillin | 35879-92-6

• 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: 8α-hydroxyachillin
• 英文别名: hydroxyachillin；(3R,3aR,4S,9aS,9bR)-4-hydroxy-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
• CAS: 35879-92-6
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: YMUOZXZDDBRJEP-SSGZPDKPSA-N

物化性质

• 熔点：
  145.5-146.5 °C
• 沸点：
  486.1±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8α-hydroxyachillin 在 亚硝酰氯 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以37%的产率得到(1S,6R,7S,10R,11S)-2-oxo-1,10-dinitroguai-3-en-6-ol-11,8-olide
  参考文献：
  名称：

  One-Step Synthesis of the Vicinal Dinitroguaianolides Achillin and Grossmisin

  摘要：

  1,10-Dihydro-1alpha,10alpha-dinitrogrossmisin was synthesized by bubbling gaseous nitrosyl chloride through a chloroform solution of the guaianolide grossmisin. The molecular structure was determined by X-ray. It was found that the formation of similar dinitrates is accelerated by using NOCl containing nitrogen dioxide.

  DOI：

  10.1023/b:conc.0000003417.79920.8d

文献信息

• Synthesis of two new chloro derivatives of the guaianolide grossmisin and the crystal structure of one derivative
  作者：O. V. Alebastrov、S. A. Pigiltsova、G. A. Atazhanova、V. A. Raldugin、M. M. Shakirov、I. Yu. Bagryanskaya、Yu. V. Gatilov、A. T. Kulyjiasov、S. M. Adekenov、G. A. Tolstikov

  DOI：10.1007/bf02494933

  日期：2000.11

  The reaction of grossmisin (8 alpha -hydroxyachillin, 1) with chlorine in benzene afforded a mixture of products. The less polar product readily crystallized after chromatography. According to the X-ray diffraction data, this product has the structure of 1 alpha ,10 beta -dichloro-1,10-dihydrogrossmisin. The second chloro derivative of grossmisin. viz., 8 beta -chloroachillin. was prepared in good yield by the reaction of lactone 1 with PCl5 in CHCl3 in the presence of Py.
• One-Step Synthesis of the Vicinal Dinitroguaianolides Achillin and Grossmisin
  作者：O. V. Alebastrov、V. A. Raldugin、I. Yu. Bagryanskaya、Yu. V. Gatilov、M. M. Shakirov、A. T. Kulyyasov、S. M. Adekenov

  DOI：10.1023/b:conc.0000003417.79920.8d

  日期：2003.7

  1,10-Dihydro-1alpha,10alpha-dinitrogrossmisin was synthesized by bubbling gaseous nitrosyl chloride through a chloroform solution of the guaianolide grossmisin. The molecular structure was determined by X-ray. It was found that the formation of similar dinitrates is accelerated by using NOCl containing nitrogen dioxide.