2-methyl-pent-2-enoic acid 1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester | 760197-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-pent-2-enoic acid 1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• 英文别名: [(1S,2R,4R)-1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (E)-2-methylpent-2-enoate
• CAS: 760197-72-6
• 化学式: C₂₈H₃₄O₃
• 分子量: 418.576
• InChiKey: VHHFOVAWBVAEMK-MPJQSLPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-pent-2-enoic acid 1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 碳酸氢钠 Oxone 、 1,1,1-三氟丙酮 、 edetate disodium 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 生成 (2R,3S)-3-Ethyl-2-methyl-oxirane-2-carboxylic acid (1S,2R,4R)-1-(hydroxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 、 (2S,3R)-3-Ethyl-2-methyl-oxirane-2-carboxylic acid (1S,2R,4R)-1-(hydroxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  在各种手性助剂衍生烯酮的非对映选择性环氧化的范围：樟脑的构象分析衍生ñ -和ö -enones

  摘要：

  用选定的氧化剂处理各种樟脑衍生的N-和O-烯酮，可在很宽的非对映选择性范围内提供相应的环氧化物。对于樟脑素衍生的活化烯烃，当用甲基（三氟甲基）二环氧乙烷处理s-反式烯酮时，可获得高至优异的立体选择性。另一方面，对于exo -10,10-diphenyl-2,10-camphanediol（3）和exo -10,10-diphenyl-10-methoxy-camphaneol（4）衍生的烯烃，使用s-cis在相同的反应条件下，烯酮得到所需的环氧化物，具有极好的非对映选择性。立体选择性高度依赖于助剂衍生的烯酮的几何形状，并讨论了立体化学诱导。

  DOI：

  10.1016/j.tet.2004.05.095
• 作为产物：
  描述：

  (E)-2-methyl-2-pentenoyl chloride 、 exo-10,10-diphenyl-2,10-camphanediol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到2-methyl-pent-2-enoic acid 1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate

  摘要：

  The treatment of a range of N- and O-enones derived from various camphor-based chiral auxiliaries A-D with N-aminoplithalimide in the presence of lead tetraacetate is described. In general, N-phtbalimidoaziridines were obtained with high diastereo-selectivities (up to 98% de) and chemical yields (up to 95%) when 10,10-diphenyl-2,10-camphanediol A derived O-enones with a range of substituents were used under the same reaction conditions. Excellent stereoselectivity was obtained when the N-tosyl camphorpyrazolidinone E derived acrylate was used. The absolute configuration of the new stereogenic center(s) of the major diastereomer was established by X-ray crystallographic analysis. Chiral auxiliary cleavage was achieved under mild reaction conditions. A model to explain the stereochemical induction is also proposed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.028