4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-vinylcyclohepta[b]furan-2-one | 1015071-39-2

• 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: 4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-vinylcyclohepta[b]furan-2-one
• 英文别名: (6S,7S,8aR)-6-hydroxy-3,7-dimethyl-6-vinyl-4,5,6,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one；(6S,7S,8aR)-4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-vinylcyclohepta[b]furan-2-one；(6S,7S,8aR)-6-ethenyl-6-hydroxy-3,7-dimethyl-5,7,8,8a-tetrahydro-4H-cyclohepta[b]furan-2-one
• CAS: 1015071-39-2
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: GDFVXKCLPVRPEW-RLCGTCKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-vinylcyclohepta[b]furan-2-one 在 甲基磺酰氯 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Total synthesis of xanthanolides

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.08.061
• 作为产物：
  描述：

  4-methyl-5-vinyl-8-oxabicyclo[3.2.1]octane-1,2-diol 、 benzyl 2-(triphenylphosphoranylidene)propanoate 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 2.5h， 生成 4,5,6,7,8,8a-hexahydro-6-hydroxy-3,7-dimethyl-6-vinylcyclohepta[b]furan-2-one
  参考文献：
  名称：

  Total synthesis of xanthanolides

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.08.061

文献信息

• Cu(II)-Catalyzed Acylation by Thiol Esters Under Neutral Conditions: Tandem Acylation-Wittig Reaction Leading to a One-Pot Synthesis of Butenolides
  作者：Kazumasa Matsuo、Mitsuru Shindo

  DOI：10.1021/ol102407k

  日期：2010.11.19

  The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push−pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.

  据报道，在中性条件下，Cu（II）盐通过推挽机制催化了醇与Wittig试剂中存在的硫醇酯的首次催化酰化作用。此外，开发了一种新的方法，用于通过铜催化剂对酰基辅酶进行单锅内酯化。显示了该方法用于合成天然产物的合成效用。
• Total Synthesis of (+)- and (−)-Sundiversifolide via Intramolecular Acylation and Determination of the Absolute Configuration
  作者：Keiko Ohtsuki、Kazumasa Matsuo、Takashi Yoshikawa、Chihiro Moriya、Kaori Tomita-Yokotani、Kozo Shishido、Mitsuru Shindo

  DOI：10.1021/ol8001333

  日期：2008.3.1

  Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The gamma-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic alpha-hydroxyhemiacetal with Ph3P=CMe(CO2R).

  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。