endo-3,3-dimethylspiro[bicyclo[2.2.1]heptane-2,2'-oxirane]

• 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: endo-3,3-dimethylspiro[bicyclo[2.2.1]heptane-2,2'-oxirane]
• 英文别名: (1S,3R,4R)-2,2-dimethylspiro[bicyclo[2.2.1]heptane-3,2'-oxirane]
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: ISNKNHAUYOWDHN-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  endo-3,3-dimethylspiro[bicyclo[2.2.1]heptane-2,2'-oxirane] 在 sodium ethanolate 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以48%的产率得到10,10-thiodi(camphan-3-ol)
  参考文献：
  名称：

  氧化莰烯与含硫亲核试剂的反应

  摘要：

  由异硫脲盐和硫脲在碱催化条件下亲核加成得到莰烯系列含硫衍生物。

  DOI：

  10.1007/bf00630010
• 作为产物：
  描述：

  (-)-莰烯 在 过氧乙酸 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 endo-3,3-dimethylspiro[bicyclo[2.2.1]heptane-2,2'-oxirane] 、 (1S,3S,4R)-2,2-dimethylspiro[bicyclo[2.2.1]heptane-3,2'-oxirane]
  参考文献：
  名称：

  Camp烯和α-and烯环氧化合物的酸催化反应

  摘要：

  Isomerization of camphene and alpha-fenchene epoxides under homogeneous and heterogeneous conditions in media of various acidity was studied. The intermolecular reactions of these epoxy compounds with unsaturated aldehydes, allyl alcohol and methanol on askanite-bentonite clay yielded spiroacetals, and open-chain hydroxyethers and acetals. The results obtained are compared to those for reactions with the initial monoterpenes.

  DOI：

  10.1023/a:1020335019901

文献信息

• Oxidation studies on some natural monoterpenes: Citral, pulegone, and camphene
  作者：E. M. Elgendy、S. A. Khayyat

  DOI：10.1134/s1070428008060067

  日期：2008.6

  Citral extracted from Cymbopogon citratus (Gramineae) was subjected to photochemical epoxidation with hydrogen peroxide to obtain a mixture of epoxy derivatives at the C-2=C-3 and C-6=C-7 double bonds. The thermal oxidation of citral with m-chloroperoxybenzoic acid at room temperature gave only the corresponding 6,7-epoxy derivative as a mixture of E and Z isomers with respect to the C-2=C-3 double bond. Photosensitized oxygenation of citral in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll lead to a mixture of two isomeric hydroperoxides, (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal and (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dienal. Epoxidation of pulegone isolated from Penny royal oil (Mentha pulegium, Lamiaceae) with hydrogen peroxide under irradiation with a sodium lamp lead to a mixture of cis- and trans-isomeric 2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-ones, whereas under conditions of photosensitized oxygenation two hydroperoxide derivatives, 2-(1-hydroperoxy-1-methylethyl)-5-methylcyclohex-2-en-1-one and 2-hydroperoxy-5-methyl-2-(1-methylethenyl)cyclohexan-1-one, were also formed. Camphene reacted with hydrogen peroxide under irradiation to give a mixture of the corresponding endo- and exo-epoxy derivatives and camphor, while its thermal oxidation with m-chloroperoxybenzoic produced only the two former.
• Aerobic oxygenation/dehydrogenation of olefins and 14-dihydropyridines catalyzed by tris(tetrazolyl enolate)iron(III) complexes
  作者：Rolf W. Saalfrank、Stefan Reihs、Martin Hug

  DOI：10.1016/s0040-4039(00)61720-3

  日期：1993.9

  The catalytic epoxidation of olefins 4 - 7 catalyzed by synthetic metalloporphyrin analogues [FeL3] 3 associated with molecular oxygen in the presence of an electron source (isobutyraldehyde) is described. Furthermore, it is shown, that 4-substituted 1,4-dihydropyridines 12 can be dehydrogenated and dealkylated, respectively, by the same system. The analogy to cytochrome P-450 is obvious.
• ——
  作者：O. I. Yarovaya、D. V. Korchagina、Yu. V. Gatilov、V. A. Barkhash

  DOI：10.1023/a:1020335019901

  日期：——

  Isomerization of camphene and alpha-fenchene epoxides under homogeneous and heterogeneous conditions in media of various acidity was studied. The intermolecular reactions of these epoxy compounds with unsaturated aldehydes, allyl alcohol and methanol on askanite-bentonite clay yielded spiroacetals, and open-chain hydroxyethers and acetals. The results obtained are compared to those for reactions with the initial monoterpenes.
• Reactions of camphene oxide with sulfur-containing nucleophiles
  作者：L. E. Nikitina、O. A. Shkuro、V. V. Plemenkov

  DOI：10.1007/bf00630010

  日期：1994.3

  Sulfur-containing derivatives of the camphene series have been obtained by the nucleophilic addition of isothiouronium salts and thiourea under the conditions of base catalysis.

  由异硫脲盐和硫脲在碱催化条件下亲核加成得到莰烯系列含硫衍生物。