(3Z)-3a,4,5,6,7,8-hexahydro-1-hydroxy-3-(2-hydroxy-2-ethylbutylidene)azulen-2(1H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3Z)-3a,4,5,6,7,8-hexahydro-1-hydroxy-3-(2-hydroxy-2-ethylbutylidene)azulen-2(1H)-one
• 英文别名: (3Z)-3-(2-ethyl-2-hydroxybutylidene)-1-hydroxy-3a,4,5,6,7,8-hexahydroazulen-2-one
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: OJUOKGOUDNJWOL-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-hydroxy-cycloheptanecarbonitrile 在 吡啶 、 sodium hydroxide 、 草酰氯 、 四丁基硫酸氢铵 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 生成 (3Z)-3a,4,5,6,7,8-hexahydro-1-hydroxy-3-(2-hydroxy-2-ethylbutylidene)azulen-2(1H)-one
  参考文献：
  名称：

  Tandem alkylation–cyclization process via an O,C-dianion

  摘要：

  A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition-deprotonation-alkylation-cyclization process is described. Addition of lithioallene 2 to enamides 1 generates tetrahedral intermediate 3. Deprotonation of the gamma carbon atom of the allene function in situ, followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenones 6. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.097

文献信息

• Tandem alkylation–cyclization process via an O,C-dianion
  作者：April R. Banaag、Gideon O. Berger、Francis Dhoro、Derrick B. delos Santos、Darryl D. Dixon、James P. Mitchell、Bradley K. Tokeshi、Marcus A. Tius

  DOI：10.1016/j.tet.2005.01.097

  日期：2005.3

  A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition-deprotonation-alkylation-cyclization process is described. Addition of lithioallene 2 to enamides 1 generates tetrahedral intermediate 3. Deprotonation of the gamma carbon atom of the allene function in situ, followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenones 6. (c) 2005 Elsevier Ltd. All rights reserved.