tert-butyl 2-[(1S)-2-hydroxy-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-1-yl]acetate | 271244-67-8

• 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: tert-butyl 2-[(1S)-2-hydroxy-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-1-yl]acetate
• CAS: 271244-67-8
• 化学式: C₁₇H₂₅NO₅
• 分子量: 323.389
• InChiKey: MCQKWYGOTZWBDP-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(1S)-2-hydroxy-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-1-yl]acetate 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 生成 Methanesulfonic acid 2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl]-ethyl ester
  参考文献：
  名称：

  Asymmetric addition of a Reformatsky-type reagent to 3,4-dihydroisoquinoline N-oxides

  摘要：

  The asymmetric addition of a Reformatsky-type reagent, prepared in situ from diethylzinc and iodoacetic acid ester, to a carbon-nitrogen double bond in 3,4-dihydroisoquinoline N-oxides was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding (S)-1-substituted 2-hydroxy-1,2,3,4-tetrahydroisoquinolines with enantioselectivities up to 86% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00003-3
• 作为产物：
  描述：

  3,4-dihydro-6,7-dimethoxyisoquinoline N-oxide 、 碘乙酸叔丁酯 在 溴丁基-镁 、 L-(+)-酒石酸二异丙酯 、 diethylzinc 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 tert-butyl 2-[(1S)-2-hydroxy-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-1-yl]acetate 、
  参考文献：
  名称：

  Asymmetric addition of a Reformatsky-type reagent to 3,4-dihydroisoquinoline N-oxides

  摘要：

  The asymmetric addition of a Reformatsky-type reagent, prepared in situ from diethylzinc and iodoacetic acid ester, to a carbon-nitrogen double bond in 3,4-dihydroisoquinoline N-oxides was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding (S)-1-substituted 2-hydroxy-1,2,3,4-tetrahydroisoquinolines with enantioselectivities up to 86% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00003-3

文献信息

• Asymmetric addition of a Reformatsky-type reagent to 3,4-dihydroisoquinoline N-oxides
  作者：Yutaka Ukaji、Yayoi Yoshida、Katsuhiko Inomata

  DOI：10.1016/s0957-4166(00)00003-3

  日期：2000.2

  The asymmetric addition of a Reformatsky-type reagent, prepared in situ from diethylzinc and iodoacetic acid ester, to a carbon-nitrogen double bond in 3,4-dihydroisoquinoline N-oxides was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding (S)-1-substituted 2-hydroxy-1,2,3,4-tetrahydroisoquinolines with enantioselectivities up to 86% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.