6-allyl-5-oxaspiro<4.5>decane | 133549-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 6-allyl-5-oxaspiro<4.5>decane
• 英文别名: 7-allyl-6-oxaspiro[4.5]decane；7-prop-2-enyl-6-oxaspiro[4.5]decane
• CAS: 133549-30-1
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: BZPCQMCIQZIMAN-UHFFFAOYSA-N

物化性质

• 沸点：
  255.4±9.0 °C(predicted)
• 密度：
  0.93±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  甲基丙烯酸乙酯 、 6-allyl-5-oxaspiro<4.5>decane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以83%的产率得到(E)-ethyl 2-methyl-4-(6-oxaspiro[4.5]decan-7-yl)but-2-enoate
  参考文献：
  名称：

  Divergent approach to the polymaxenolide and pinnaic acid cores

  摘要：

  The divergent syntheses of the spirocyclic pyran core of polymaxenolide and the spirocyclic piperidine core of pinnaic acid have been achieved. Our divergent approach takes advantage of highly efficient Achmatowicz and aza-Achmatowicz rearrangements to generate the highly functionalised cores, which are then regioselectively modified. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.047
• 作为产物：
  描述：

  (+/-)-2-(1'-hydroxy-cyclopentyl)-furane 在 (triphenylphosphine)copper(I) hydride hexamer 、 三氟化硼乙醚 、 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 hexanes 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 苯 为溶剂， 反应 21.25h， 生成 6-allyl-5-oxaspiro<4.5>decane
  参考文献：
  名称：

  Divergent approach to the polymaxenolide and pinnaic acid cores

  摘要：

  The divergent syntheses of the spirocyclic pyran core of polymaxenolide and the spirocyclic piperidine core of pinnaic acid have been achieved. Our divergent approach takes advantage of highly efficient Achmatowicz and aza-Achmatowicz rearrangements to generate the highly functionalised cores, which are then regioselectively modified. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.047

文献信息

• Masked lithium bishomoenolates: useful intermediates in organic synthesis
  作者：Diego J. Ramon、Miguel Yus

  DOI：10.1021/jo00012a012

  日期：1991.6

  The lithiation of the chloro ketals 9 with lithium naphthalenide at -78-degrees-C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCHO, PhCHO, MeCOEt, (activated CH2)4CO, (activated CH2)5CO, (activated CH2)7CO, PhCOMe, c-C3H5COPh, PhCN, HCONMe2, PrCO activated N(CH2)4, PhCO activated N(CH2)4, PhCOCl, EtOCOCl, PhCHNPh, and (PhCH2S)2) to give, after hydrolysis with water, the corresponding bifunctionalized compounds 10a-22a, 10b-22b, and 10c-15c. When alkyl halides were used as electrophiles the reaction failed. In the presence of a catalytic amount of the complex CuBr.Me2S, the same reaction with alpha,beta-unsaturated ketones (methyl vinyl ketone or 2-cyclohexanone) yielded the expected products of a 1,4-addition 25a-c and 26b. The deprotection of the masked carbonyl group was easily done by treatment with 2 N hydrochloric acid in THF, so as examples, compounds 27a-29a, 30b, 31b, 32c, and 33c were isolated. The transformation of hemiacetals of the type 27a into substituted tetrahydropyrans was carried out by means of compounds of the type R3SiNu (Nu = H, allyl, CN) in the presence of BF3, so products 34a-41a, 42b, and 43b were prepared. Finally, the in situ oxidation of the deprotected products of the type 27a-arising from the reaction of bishomoenolate 4a with carbonyl compounds-with Jones reagent (for ketones derivatives) or PCC (for aldehydes derivatives) led to the corresponding delta-lactones 44-57.
• RAMON, DIEGO J.;YUS, MIGUEL, J. ORG. CHEM., 56,(1991) N2, C. 3825-3831
  作者：RAMON, DIEGO J.、YUS, MIGUEL

  DOI：——

  日期：——