1-[5'-chloro-2'-(methylamino)phenyl]-1,2,3,4-tetrahydroisoquinoline isobutylidene aminal | 249587-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 1-[5'-chloro-2'-(methylamino)phenyl]-1,2,3,4-tetrahydroisoquinoline isobutylidene aminal
• 英文别名: (13bR)-2-chloro-5-methyl-6-propan-2-yl-6,8,9,13b-tetrahydroisoquinolino[2,1-c]quinazoline
• CAS: 249587-50-6
• 化学式: C₂₀H₂₃ClN₂
• 分子量: 326.869
• InChiKey: XBSDRVLMVXVBCE-FIWHBWSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[5'-chloro-2'-(methylamino)phenyl]-1,2,3,4-tetrahydroisoquinoline isobutylidene aminal 在 盐酸 、 nitronium tetrafluoborate 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 15.0h， 生成 1-[5'-nitro-2'-(methylamino)phenyl]-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Enantioselective Enolate Protonation:  Matching Chiral Aniline and Substrate Acidity

  摘要：

  A comparison of chiral anilines 1a-f in the asymmetric protonation of enolate 15 shows that the optimum Delta pK(a) value (chiral acid vs protonated enolate) for the highest enantioselectivity is ca. 3 (Table 2). An extension of this concept to amino acid enolates was possible, and le was found to give the best enantioselectivity (85% ee) with the alanine-derived N-lithioenolate 5a (Table 3). Changes in aniline pK(a) due to variation of substituents at the aniline nitrogen were evaluated briefly, but these changes did not show consistent trends in the enantioselectivity vs pK(a).

  DOI：

  10.1021/jo990897m
• 作为产物：
  描述：

  异丁醛 、 (-)-1-<5-chloro-2-(methylamino)phenyl>-1,2,3,4-tetrahydroquinoline 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到1-[5'-chloro-2'-(methylamino)phenyl]-1,2,3,4-tetrahydroisoquinoline isobutylidene aminal
  参考文献：
  名称：

  Enantioselective Enolate Protonation:  Matching Chiral Aniline and Substrate Acidity

  摘要：

  A comparison of chiral anilines 1a-f in the asymmetric protonation of enolate 15 shows that the optimum Delta pK(a) value (chiral acid vs protonated enolate) for the highest enantioselectivity is ca. 3 (Table 2). An extension of this concept to amino acid enolates was possible, and le was found to give the best enantioselectivity (85% ee) with the alanine-derived N-lithioenolate 5a (Table 3). Changes in aniline pK(a) due to variation of substituents at the aniline nitrogen were evaluated briefly, but these changes did not show consistent trends in the enantioselectivity vs pK(a).

  DOI：

  10.1021/jo990897m

文献信息

• Enantioselective Enolate Protonation:  Matching Chiral Aniline and Substrate Acidity
  作者：E. Vedejs、A. W. Kruger、E. Suna

  DOI：10.1021/jo990897m

  日期：1999.10.1

  A comparison of chiral anilines 1a-f in the asymmetric protonation of enolate 15 shows that the optimum Delta pK(a) value (chiral acid vs protonated enolate) for the highest enantioselectivity is ca. 3 (Table 2). An extension of this concept to amino acid enolates was possible, and le was found to give the best enantioselectivity (85% ee) with the alanine-derived N-lithioenolate 5a (Table 3). Changes in aniline pK(a) due to variation of substituents at the aniline nitrogen were evaluated briefly, but these changes did not show consistent trends in the enantioselectivity vs pK(a).