4-(7,7-dimethyl-3-oxatricyclo[4.1.1.0^2,4]oct-2-yl)-3-thiabutanoate de methyle | 249647-44-7

• 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: 4-(7,7-dimethyl-3-oxatricyclo[4.1.1.0^2,4]oct-2-yl)-3-thiabutanoate de methyle
• 英文别名: methyl 2-[[(1R,2R,4S,6R)-7,7-dimethyl-3-oxatricyclo[4.1.1.02,4]octan-2-yl]methylsulfanyl]acetate
• CAS: 249647-44-7
• 化学式: C₁₃H₂₀O₃S
• 分子量: 256.366
• InChiKey: NTVZMUKWJYWEDV-ORXSELOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(7,7-dimethyl-3-oxatricyclo[4.1.1.0^2,4]oct-2-yl)-3-thiabutanoate de methyle 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以28%的产率得到{{[(4R)-3,3-dimethyl-4-(2-oxoethyl)cyclopent-1-enyl]methyl}thio}acetate de methyle
  参考文献：
  名称：

  摘要：

  The functionalized 2,3-epoxypinanes 1b-i were submitted to isomerization in the presence of ZnBr2 at 110 degrees (Table 1) or of BF3. Et2O at different temperatures (Table 2), and their behavior was compared with that of the non-functionalized parent 1a and with similar known transpositions. The produced campholenals 2, pinocamphones 3, and in some cases, fencholenals 4 were isolated and characterized. A mechanism involving a concerted oxirane ring opening is proposed (Scheme 4).

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<616::aid-hlca616>3.0.co;2-m
• 作为产物：
  描述：

  tert-Butyl 6,6-dimethyl-2-methylenebicyclo[3.1.1]hept-3-yl peroxide 、 巯基乙酸甲酯 反应 2.0h， 以88%的产率得到4-(7,7-dimethyl-3-oxatricyclo[4.1.1.0^2,4]oct-2-yl)-3-thiabutanoate de methyle
  参考文献：
  名称：

  A General And Easy Synthesis of Pinene Oxides Functionalized at C-10

  摘要：

  DOI：

  10.1055/s-1999-3574

文献信息

• Réaction compétitive de la substitution homolytique intramoléculaire : décomposition de pero×ydes allyliques dans le thioglycolate de méthyle
  作者：Marie-Josèphe Bourgeois、Marianne Vialemaringe、Monique Campagnole、Evelyne Montaudon

  DOI：10.1139/cjc-79-3-257

  日期：——

  The decomposition of allylic peroxides in methyl thioglycolate always leads to both epoxide and adduct peroxide. According to the nature of the allylic chain, either epoxide or peroxide is the predominant product, if not the only one. It is the first example where the hydrogen transfer is as fast as the intramolecular homolytic substitution. The influence of different factors upon the competition is studied.