1,4-二氧杂螺[4.5]癸-7-烯,7-乙基-9,9-二甲基- | 134963-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,4-二氧杂螺[4.5]癸-7-烯,7-乙基-9,9-二甲基-
• 英文名称: 7-Ethyl-9,9-dimethyl-1,4-dioxaspiro<4.5>dec-7-ene
• 英文别名: 9-ethyl-7,7-dimethyl-1,4-dioxaspiro[4.5]dec-8-ene
• CAS: 134963-08-9
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: ALBAZSBUPUWCCF-UHFFFAOYSA-N

物化性质

• 沸点：
  256.4±40.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,4-二氧杂螺[4.5]癸-7-烯,7-乙基-9,9-二甲基- 在 palladium on activated charcoal sodium tetrahydroborate 、 二甲基硫 、 三氟化硼乙醚 、 potassium tert-butylate 、 氢气 、 对甲苯磺酸 、 臭氧 作用下， 以 甲醇 、 苯 为溶剂， 生成 (+/-)-pentalenene
  参考文献：
  名称：

  A stereoselective route to (±)-pentalenene and (±)-9-epi-pentalenene

  摘要：

  通过一种新颖的螺环化策略合成了（±）-五亚甲基1和（±）-表五亚甲基12，该策略允许通过醛缩合反应形成五个成员环中的两个环；通过双环中间体8中两个双键的还原顺序，以立体选择性方式形成C-9的两种对映异构体。

  DOI：

  10.1039/c39910000764
• 作为产物：
  描述：

  3-乙氧基-5,5-二甲基-2-环己烯-1-酮 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 1.0h， 生成 1,4-二氧杂螺[4.5]癸-7-烯,7-乙基-9,9-二甲基-
  参考文献：
  名称：

  Spiroannulation approach to pentalenene, an angular triquinane sesquiterpene

  摘要：

  The route to the angular triquinane (+/-)-pentalenene (la) followed from an efficient geminal acylation of the acetal of isophorone or its homolog 6b by 1,2-bis((trimethylsilyl) oxy) cyclobutene (3) in the presence of boron trifluoride etherate. Ring cleavage and reclosure (9 --> 11) secured the required spiro[4.4]nonane system with a pendant ketone function in place for the closure of the final, central : I ring. The relative stereochemistry at C-9 was established during hydrogenation over palladium of the C-3 double bond of 11, but the facial selectivity was determined by the mode of reduction of the conjugated, orthogonal double bond at C-6 of 11. After cyclization to the enone 17b, the synthesis was completed by reductions of both the double bond and the ketone and simple dehydration. The 9-epi isomer (26) of (+/-)-pentalenene was synthesized also.

  DOI：

  10.1021/jo00080a018

文献信息

• Spiroannulation approach to pentalenene, an angular triquinane sesquiterpene
  作者：Y.-J. Wu、Y.-Y. Zhu、D. Jean Burnell

  DOI：10.1021/jo00080a018

  日期：1994.1

  The route to the angular triquinane (+/-)-pentalenene (la) followed from an efficient geminal acylation of the acetal of isophorone or its homolog 6b by 1,2-bis((trimethylsilyl) oxy) cyclobutene (3) in the presence of boron trifluoride etherate. Ring cleavage and reclosure (9 --> 11) secured the required spiro[4.4]nonane system with a pendant ketone function in place for the closure of the final, central : I ring. The relative stereochemistry at C-9 was established during hydrogenation over palladium of the C-3 double bond of 11, but the facial selectivity was determined by the mode of reduction of the conjugated, orthogonal double bond at C-6 of 11. After cyclization to the enone 17b, the synthesis was completed by reductions of both the double bond and the ketone and simple dehydration. The 9-epi isomer (26) of (+/-)-pentalenene was synthesized also.
• A stereoselective route to (±)-pentalenene and (±)-9-epi-pentalenene
  作者：Yong-Jin Wu、D. Jean Burnell

  DOI：10.1039/c39910000764

  日期：——

  The (±)-pentalenene 1 and (±)-epi-pentalenene 12 have been synthesised by a novel spiro-annulation strategy that allowed the subsequent formation of two of the five-membered rings by aldol condensations; the order of reduction of two double bonds in a bicyclic intermediate 8 led, in a Stereoselective manner, to one C-9 epimer or the other.

  通过一种新颖的螺环化策略合成了（±）-五亚甲基1和（±）-表五亚甲基12，该策略允许通过醛缩合反应形成五个成员环中的两个环；通过双环中间体8中两个双键的还原顺序，以立体选择性方式形成C-9的两种对映异构体。