[(1R,2R,3S,5S)-3-[(2-methoxyphenyl)methyl]-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl] 3-oxobutanoate | 198027-55-3

• 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,3S,5S)-3-[(2-methoxyphenyl)methyl]-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl] 3-oxobutanoate
• CAS: 198027-55-3
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: YXQXVQBWYQHDMA-NHAYFPRASA-N

物化性质

• 沸点：
  435.391±20.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.124±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  色醇 、 [(1R,2R,3S,5S)-3-[(2-methoxyphenyl)methyl]-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl] 3-oxobutanoate 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(1-Methyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid (1R,2R,3S,5S)-3-(2-methoxy-benzyl)-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl ester
  参考文献：
  名称：

  由（1S）-（-）-β-pine烯衍生的新手性助剂介导的不对称Friedel-Crafts反应：（-）-8-Norethyl，1'-normethyl Etodolac的对映选择性合成

  摘要：

  通过三苯酚4和手性β-酮丁酸酯5h之间的Friedel-Crafts烷基化反应，在ee中最多可合成95％的（-）-8-正乙基，1'-正甲基Etodolac（-）-7 ，然后进行水解。

  DOI：

  10.1016/s0040-4039(97)01658-4
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 、 (1R,2R,3S,5S)-3-[(2-methoxyphenyl)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-2-ol 以 甲苯 为溶剂， 反应 2.0h， 生成 丙酮 、 [(1R,2R,3S,5S)-3-[(2-methoxyphenyl)methyl]-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl] 3-oxobutanoate
  参考文献：
  名称：

  The Use of Chiral Auxiliaries Prepared from (-)-β-Pinene in Stereoselective Reduction of β-Ketobutyrates

  摘要：

  Chiral auxiliaries previously prepared from (-)-beta-pinene (3), alcohols 5a-e and 6, were transformed into beta-ketobutyrates 7a-e and 8 respectively. These compounds were stereoselectively reduced by NaBH4 in the presence of additives (MnCl2 or CaCl2), leading to the corresponding beta-hydroxy butyrates 10a-e and 11 in good chemical yield and poor to moderate stereoselectivities (de 0%-60%). The configuration at the newly generated stereogenic center in 10a was determined to be S through its transformation into S-(+)-butanediol.

  DOI：

  10.1080/00397910008087342

文献信息

• Asymmetric Friedel-Crafts reaction mediated by new chiral auxiliaries derived from (1S)-(−)-β-pinene: Enantioselective synthesis of (−)-8-Norethyl, 1′-normethyl Etodolac
  作者：Paulo R.R. Costa、Lúcio M. Cabral、Karla G. Alencar、Luciana L. Schmidt、Mário L.A.A. Vasconcellos

  DOI：10.1016/s0040-4039(97)01658-4

  日期：1997.10

  (−)-8-Norethyl, 1′-normethyl Etodolac (−)-7 was synthesized in ee up to 95% from a Friedel-Crafts alkylation reaction between tryptophol 4 and the chiral β-ketobutyrate 5h, followed by hydrolysis.

  通过三苯酚4和手性β-酮丁酸酯5h之间的Friedel-Crafts烷基化反应，在ee中最多可合成95％的（-）-8-正乙基，1'-正甲基Etodolac（-）-7 ，然后进行水解。
• The Use of Chiral Auxiliaries Prepared from (-)-β-Pinene in Stereoselective Reduction of β-Ketobutyrates
  作者：Karla G. Alencar、Ubiracir F.L. Filho、Mário L. A. A. Vasconcellos、Paulo R.R. Costa

  DOI：10.1080/00397910008087342

  日期：2000.2

  Chiral auxiliaries previously prepared from (-)-beta-pinene (3), alcohols 5a-e and 6, were transformed into beta-ketobutyrates 7a-e and 8 respectively. These compounds were stereoselectively reduced by NaBH4 in the presence of additives (MnCl2 or CaCl2), leading to the corresponding beta-hydroxy butyrates 10a-e and 11 in good chemical yield and poor to moderate stereoselectivities (de 0%-60%). The configuration at the newly generated stereogenic center in 10a was determined to be S through its transformation into S-(+)-butanediol.