2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline | 102922-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: (4S)-2-(3,4-dihydro-1H-isoquinolin-2-yl)-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 102922-30-5
• 化学式: C₁₅H₂₀N₂O
• 分子量: 244.337
• InChiKey: BITWJSBPNFIIPV-CQSZACIVSA-N

物化性质

• 沸点：
  353.2±52.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline 在 对甲苯磺酸 叔丁基锂 、 sodium ethanolate 、 对甲苯磺酸 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 18.33h， 生成 1-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1,2,3,6-tetrahydro-pyridine
  参考文献：
  名称：

  Chiral dipole-stabilized anions: experiment and theory in benzylic and allylic systems. Stereoselective deprotonations, pyramidal inversions, and stereoselective alkylations of lithiated (tetrahydroisoquinolyl)oxazolines

  摘要：

  DOI：

  10.1021/ja00188a040
• 作为产物：
  描述：

  (S)-4-isopropyl-2-((R)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-4,5-dihydrooxazole 在 对甲苯磺酸 sodium ethanolate 、 对甲苯磺酸 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 18.0h， 生成 2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Chiral dipole-stabilized anions: experiment and theory in benzylic and allylic systems. Stereoselective deprotonations, pyramidal inversions, and stereoselective alkylations of lithiated (tetrahydroisoquinolyl)oxazolines

  摘要：

  DOI：

  10.1021/ja00188a040

文献信息

• 1-Magnesiotetrahydroisoquinolyloxazolines as Chiral Nucleophiles in Stereoselective Additions to Aldehydes:  Auxiliary Optimization, Asymmetric Synthesis of (+)-Corlumine, (+)-Bicuculline, (+)-Egenine, and (+)-Corytensine, and Preliminary ¹³C NMR Studies of 1-Lithio- and 1-Magnesiotetrahydroisoquinolyloxazolines
  作者：Robert E. Gawley、Pingsheng Zhang

  DOI：10.1021/jo961164u

  日期：1996.11.15

  Transmetalation of 1-lithiotetrahydroisoquinolyloxazolines with magnesium halides affords Grignard reagents that add to aldehydes with up to 80% selectivity for one of the four possible diastereomeric products. An oxazoline chiral auxiliary derived from camphor provides an optimal blend of diastereoselectivity and isomer separability. Synthetic applications of the optimal auxiliary, patterned after a literature approach in the racemic series, comprise an improved (formal) synthesis of bicuculline, egenine, and corytensine, as well as an efficient synthesis of corlumine. Preliminary NMR studies show that both 1-lithio- and 1-magnesiotetrahydroisoquinolyloxazolines are dynamic mixtures in THF solution at low temperatures. The barrier to pyramidal inversion of the secondary Grignard reagent is in the 9.8-10.1 kcal/mol range, while an upper limit of about 8.2 kcal/mol can be assigned to the barrier to the organolithium inversion.
• Oxazoline-mediated asymmetric alkylation of amines
  作者：Robert E. Gawley、Georgina Hart、Marta Goicoechea-Pappas、Arthur L. Smith

  DOI：10.1021/jo00365a049

  日期：1986.7
• Thermodynamic control in the asymmetric alkylation of the dipole-stabilized anions of chiral aminooxazolines
  作者：Robert E. Gawley

  DOI：10.1021/ja00238a057

  日期：1987.2
• GAWLEY R. E., J. AMER. CHEM. SOC., 109,(1987) N 4, 1265-1266
  作者：GAWLEY R. E.

  DOI：——

  日期：——