(R)-(+)-N-acetylcalycotomine | 841-93-0

• 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: (R)-(+)-N-acetylcalycotomine
• 英文别名: N-acetylcalycotomine；1-[(1R)-1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethanone
• CAS: 841-93-0
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: MGFDQLHBYAFIFZ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-N-acetylcalycotomine 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以91%的产率得到(R)-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methanol
  参考文献：
  名称：

  Czarnocki, Zbigniew, Journal of Chemical Research, Miniprint, 1992, # 10, p. 2801 - 2819

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (R)-(+)-N-acetylcalycotomine
  参考文献：
  名称：

  (S)-(−)-α-Methylbenzylamine as an efficient chiral auxiliary in enantiodivergent synthesis of both enantiomers of N-acetylcalycotomine

  摘要：

  (S)-(-)-alpha-Methylbenzylamine 2 was used as a chiral auxiliary in the enantiodivergent synthesis of simple isoquinoline alkaloids. The prochiral imine moiety in compound 4 was reduced with different reagents, giving diastereomeric amines 5a or 5b, which subsequently were transformed to either (S)-(-)-N-acetylcalycotomine 6 or (R)-(+)-N-acetylcalycotomine ent-6 in good enantiomeric excess. F-19 NMR of its Mosher's acid ester was used to establish the purities of final compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00370-5

文献信息

• Czarnocki, Zbigniew, Journal of Chemical Research, Miniprint, 1992, # 10, p. 2801 - 2819
  作者：Czarnocki, Zbigniew

  DOI：——

  日期：——
• (S)-(−)-α-Methylbenzylamine as an efficient chiral auxiliary in enantiodivergent synthesis of both enantiomers of N-acetylcalycotomine
  作者：Marek Ziółkowski、Zbigniew Czarnocki、Andrzej Leniewski、Jan K. Maurin

  DOI：10.1016/s0957-4166(99)00370-5

  日期：1999.8

  (S)-(-)-alpha-Methylbenzylamine 2 was used as a chiral auxiliary in the enantiodivergent synthesis of simple isoquinoline alkaloids. The prochiral imine moiety in compound 4 was reduced with different reagents, giving diastereomeric amines 5a or 5b, which subsequently were transformed to either (S)-(-)-N-acetylcalycotomine 6 or (R)-(+)-N-acetylcalycotomine ent-6 in good enantiomeric excess. F-19 NMR of its Mosher's acid ester was used to establish the purities of final compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.