(1'R,2'S,5'R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-benzoylacrylate | 115704-79-5

• 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: (1'R,2'S,5'R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-benzoylacrylate
• 英文别名: 1-benzoyl-1-phenylmenthyloxycarbonylethene；[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-benzoylprop-2-enoate
• CAS: 115704-79-5
• 化学式: C₂₆H₃₀O₃
• 分子量: 390.522
• InChiKey: RLBUQJROLUYKQM-SXSPYAJSSA-N

物化性质

• 沸点：
  507.1±42.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'R,2'S,5'R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-benzoylacrylate 、 环戊二烯 以91%的产率得到
  参考文献：
  名称：

  YAMAUCHI, MASASHIGE;WATANABE, TOSHIO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 1, 27-28

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-phenyl-1,3-dioxolan-2-yl)acetyl chloride 在 盐酸 、 4-二甲氨基吡啶 、 sodium periodate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 63.0h， 生成 (1'R,2'S,5'R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-benzoylacrylate
  参考文献：
  名称：

  Reactivity of 2-Methylene-1,3-dicarbonyl Compounds. Stereoselective and Asymmetric Diels−Alder Reactions

  摘要：

  The Diels-Alder reaction of 1,1-dicarbonylethenes 1 with dienes was investigated. The adduct of the reaction of 1, whose two carbonyl groups were different, with cyclopentadiene showed moderate stereoselectivity and this was explained by FMO theory. However, in the Lewis acid-catalyzed addition, the reaction proceeded with high stereoselectivity to give the exo adduct 3x. This might be due to steric hindrance because the benzene ring cannot orient in the plane of the conjugated system in the metal-chelated enedione 6. Applying this principle to (1'R,2'S,5'R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 2-benzoylacrylate (1d), we achieved a diastereomeric Diels-Alder reaction to afford 3x-R, whose structure was confirmed by the X-ray crystal analysis.

  DOI：

  10.1021/jo9518819

文献信息

• High asymmetric induction in the Diels–Alder reactions of 1-benzoyl-1-phenyl-menthyloxycarbonylethene
  作者：Masashige Yamauchi、Toshio Watanabe

  DOI：10.1039/c39880000027

  日期：——

  Lewis acid catalysed Diels–Alder reaction of 1-benzoyl-1-phenylmenthyloxycarbonylethene (1d) gave the exo adduct regio- and diastero-selectively.

  路易斯酸催化的1-苯甲酰基-1-苯基薄荷基氧羰基乙烯（1d）的Diels-Alder反应给出了区域外和非对映选择性的外加合物。