4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-(oxiran-2-yl)cyclohepta[b]furan-2-one | 1015071-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-(oxiran-2-yl)cyclohepta[b]furan-2-one
• 英文别名: (6R,7S,8aR)-6-hydroxy-3,7-dimethyl-6-(oxiran-2-yl)-4,5,6,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
• CAS: 1015071-42-7
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: FLQILAYWUIYLHY-POIVVALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  59.06
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-(oxiran-2-yl)cyclohepta[b]furan-2-one 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 以14%的产率得到octahydro-6-hydroxy-3,7-dimethyl-6-(oxiran-2-yl)cyclohepta[b]furan-2-one
  参考文献：
  名称：

  Synthesis of diversifolide and structure revision

  摘要：

  The synthesis of diversifolide and its structural revision are reported. We synthesized the assigned structure of diversifolide via two methods, but the NMR spectra of the synthetic material did not match those of the natural material. Through careful investigation, we found that the spectra were identical with those of 11-epi-sundiversifolide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.141
• 作为产物：
  描述：

  4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-vinylcyclohepta[b]furan-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以96%的产率得到4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-(oxiran-2-yl)cyclohepta[b]furan-2-one
  参考文献：
  名称：

  通过分子内酰化和绝对构型的确定，合成（+）-和（-）-sundiversifolide。

  摘要：

  有机锂的分子内酰化导致sundiversifolide的两个对映异构体的有效立体控制的全合成。通过HPLC分析和化感作用测定法确定绝对构型。通过将双环α-羟基半缩醛与Ph3P = CMe（CO2R）缩合获得由丁烯内酯产生的gamma-lactone部分。

  DOI：

  10.1021/ol8001333

文献信息

• Total synthesis of xanthanolides
  作者：Kazumasa Matsuo、Keiko Ohtsuki、Takashi Yoshikawa、Kozo Shishido、Kaori Yokotani-Tomita、Mitsuru Shindo

  DOI：10.1016/j.tet.2010.08.061

  日期：2010.10

  The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), dihydroxanthatin (2), and xanthatin (3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide. (C) 2010 Elsevier Ltd. All rights reserved.