1-[(1S)-6,7-dimethoxy-1-[(1R,2R,3R,4S)-1,2,3,4,5-pentahydroxypentyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone | 182892-22-4

• 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: 1-[(1S)-6,7-dimethoxy-1-[(1R,2R,3R,4S)-1,2,3,4,5-pentahydroxypentyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone
• CAS: 182892-22-4
• 化学式: C₁₈H₂₇NO₈
• 分子量: 385.414
• InChiKey: ZFTLIMIUIWXZEQ-IHXXTUNLSA-N

物化性质

• 沸点：
  735.0±60.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  140
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[(1S)-6,7-dimethoxy-1-[(1R,2R,3R,4S)-1,2,3,4,5-pentahydroxypentyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 、 periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.58h， 生成 R-四氢罂粟碱
  参考文献：
  名称：

  Enantioselective synthesis of (R)-(−)-laudanosine and (R)-(−)-glaucine from L-ascorbic acid

  摘要：

  L-Ascorbic acid 1 was converted into L-gulonolactone 2 by catalytic hydrogenation. Treatment of 2 with 3,4-dimethoxyphenylethyl amine 3 afforded amide 4, which in several steps was transformed into the title alkaloids in good enantiomeric excesses. Also, chromium(III) oxide is proposed as an effective catalyst for the conversion of (R)-(-)-laudanosine into (R)-(-)-glaucine. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00349-7
• 作为产物：
  描述：

  Acetic acid (1R,2R,3R,4S)-2,3,4,5-tetraacetoxy-1-((S)-2-acetyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-pentyl ester 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以83%的产率得到1-[(1S)-6,7-dimethoxy-1-[(1R,2R,3R,4S)-1,2,3,4,5-pentahydroxypentyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone
  参考文献：
  名称：

  Enantioselective synthesis of (R)-(−)-laudanosine and (R)-(−)-glaucine from L-ascorbic acid

  摘要：

  L-Ascorbic acid 1 was converted into L-gulonolactone 2 by catalytic hydrogenation. Treatment of 2 with 3,4-dimethoxyphenylethyl amine 3 afforded amide 4, which in several steps was transformed into the title alkaloids in good enantiomeric excesses. Also, chromium(III) oxide is proposed as an effective catalyst for the conversion of (R)-(-)-laudanosine into (R)-(-)-glaucine. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00349-7

文献信息

• Enantioselective synthesis of (R)-(−)-laudanosine and (R)-(−)-glaucine from L-ascorbic acid
  作者：Zbigniew Czarnocki、Józef B. Mieczkowski、Marek Ziólkowski

  DOI：10.1016/0957-4166(96)00349-7

  日期：1996.9

  L-Ascorbic acid 1 was converted into L-gulonolactone 2 by catalytic hydrogenation. Treatment of 2 with 3,4-dimethoxyphenylethyl amine 3 afforded amide 4, which in several steps was transformed into the title alkaloids in good enantiomeric excesses. Also, chromium(III) oxide is proposed as an effective catalyst for the conversion of (R)-(-)-laudanosine into (R)-(-)-glaucine. Copyright (C) 1996 Published by Elsevier Science Ltd