8-hydroxy-4,5,5-trimethyl-1,6,7-trioxaspirotricyclo[2.4.0.5]tetradecan-2-one | 391624-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 8-hydroxy-4,5,5-trimethyl-1,6,7-trioxaspirotricyclo[2.4.0.5]tetradecan-2-one
• 英文别名: Hnpqgdggjwveax-uhfffaoysa-；7'a-hydroxy-3',3',4'-trimethylspiro[cyclohexane-1,7'-furo[3,4-c][1,2]dioxine]-5'-one
• CAS: 391624-10-5
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: HNPQGDGGJWVEAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-hydroxy-4,5,5-trimethyl-1,6,7-trioxaspirotricyclo[2.4.0.5]tetradecan-2-one 在 iron(II) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以84%的产率得到4,5,5-trimethyl-2-oxofuran-3-carboxylic acid
  参考文献：
  名称：

  Hydroperoxide and Endoperoxide Lactones from Photooxygenation of 3-Alkylidenedihydrofuran-2,4-diones

  摘要：

  3-Alkylidenedihydrofuran-2,4-diones 1 can be photooxygenated with O-2/TBHP to hydroperoxides 3 which slowly decompose to diols 5. Stable endoperoxides 4 are best prepared by photooxygenation of 1 with 2 equiv of O-2 in the presence of CuSO4 and p-TosOH following a nonradical mechanism. They are rapidly reduced by anhydrous FeBr2 to give butenolide 9 indicating a potential antimalarial activity.

  DOI：

  10.1021/jo030270a
• 作为产物：
  描述：

  3-(1',2'-dimethylpropylidene)-1-oxa-spiro[4,5]decane-2,4-dione 在 air 作用下， 以 氯仿 、 正戊烷 为溶剂， 反应 5.0h， 以80%的产率得到8-hydroxy-4,5,5-trimethyl-1,6,7-trioxaspirotricyclo[2.4.0.5]tetradecan-2-one
  参考文献：
  名称：

  Oxidations of 3-alkenyltetronic acids with dimethyldioxirane (DMD) and air: regioselectivity and formation of a spirotricyclic hemiketal endoperoxide lactone

  摘要：

  3-烯丙基四氢呋喃酸1的内循环CC键可被二甲基二氧杂环己烷选择性氧化，生成3-烯丙基-3-羟基二氢呋喃-2,4-二酮2，而3-外烯丙基二氢呋喃-2,4-二酮9则迅速自动氧化，生成螺三环半缩醛内过氧化物内酯10。

  DOI：

  10.1039/b104227k

文献信息

• Oxidations of 3-alkenyltetronic acids with dimethyldioxirane (DMD) and air: regioselectivity and formation of a spirotricyclic hemiketal endoperoxide lactone
  作者：Rainer Schobert、Sven Siegfried、Jochen Weingärtner、Mark Nieuwenhuyzen

  DOI：10.1039/b104227k

  日期：——

  The endocyclic CC bond of 3-allyltetronic acid 1 can be selectively oxidised with dimethyldioxirane to give 3-allyl-3-hydroxydihydrofuran-2,4-dione 2 while 3-exo-alkylidenedihydrofuran-2,4-diones 9 are rapidly autooxidised to furnish the spirotricyclic hemiketal endoperoxide lactones 10.

  3-烯丙基四氢呋喃酸1的内循环CC键可被二甲基二氧杂环己烷选择性氧化，生成3-烯丙基-3-羟基二氢呋喃-2,4-二酮2，而3-外烯丙基二氢呋喃-2,4-二酮9则迅速自动氧化，生成螺三环半缩醛内过氧化物内酯10。
• Hydroperoxide and Endoperoxide Lactones from Photooxygenation of 3-Alkylidenedihydrofuran-2,4-diones
  作者：Rainer Schobert、Ralf Stehle、Wolfgang Milius

  DOI：10.1021/jo030270a

  日期：2003.12.1

  3-Alkylidenedihydrofuran-2,4-diones 1 can be photooxygenated with O-2/TBHP to hydroperoxides 3 which slowly decompose to diols 5. Stable endoperoxides 4 are best prepared by photooxygenation of 1 with 2 equiv of O-2 in the presence of CuSO4 and p-TosOH following a nonradical mechanism. They are rapidly reduced by anhydrous FeBr2 to give butenolide 9 indicating a potential antimalarial activity.

表征谱图