(1R,2R,4S,6R)-α,7,7-trimethyl-3-oxatricyclo[4.1.1.0^2,4]octane-2-propanoate de methyle | 249647-35-6

• 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: (1R,2R,4S,6R)-α,7,7-trimethyl-3-oxatricyclo[4.1.1.0^2,4]octane-2-propanoate de methyle
• 英文别名: methyl 3-[(1R,2R,4S,6R)-7,7-dimethyl-3-oxatricyclo[4.1.1.02,4]octan-2-yl]-2-methylpropanoate
• CAS: 249647-35-6
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: BRWIHNUFVVGBDX-HYPJUYLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,6R)-α,7,7-trimethyl-3-oxatricyclo[4.1.1.0^2,4]octane-2-propanoate de methyle 在 zinc dibromide 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以37%的产率得到(4R)-α-methyl-5,5-dimethyl-4-(2-oxoethyl)cyclopent-1-ene-1-propanoate 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：

  丙酸甲酯 、 tert-Butyl 6,6-dimethyl-2-methylenebicyclo[3.1.1]hept-3-yl peroxide 在 过氧化乙酸叔丁酯 作用下， 反应 12.0h， 以60%的产率得到(1R,2R,4S,6R)-α,7,7-trimethyl-3-oxatricyclo[4.1.1.0^2,4]octane-2-propanoate 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

• Epoxyestersp-menthaniques et pinaniques en milieu basique - Parfum de noix de coco
  作者：Marie-Josèphe Bourgeois、Evelyne Montaudon

  DOI：10.1002/1522-2675(20010815)84:8<2430::aid-hlca2430>3.0.co;2-o

  日期：2001.8.15

  Base-Induced Reactions of p-Menthane- and Pinane-Derived Epoxyesters – Coconut Fragrance The base-induced isomerization of p-menthane- and pinane-derived epoxy esters was studied. The reaction is dependent on the structure of the terpene compound, the nature of the base, and experimental conditions. Among all the new synthesized compounds, one, 6a, emits a very strong fragrance of coconut. In the structure
• Isomérisation d'époxypinanes fonctionnels en milieu basique
  作者：Marianne Vialemaringe、Marie-Josèphe Bourgeois、Monique Campagnole、Evelyne Montaudon

  DOI：10.1016/s0040-4039(00)00757-7

  日期：2000.6

  Functional pinocarveols and bifunctional spiropinanes could be prepared by basic isomerisation of 2,3-epoxypinanes bearing a function or a functional chain on the carbone 10. Preliminary results are presented, which illustrate a general synthesis of these new compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.