阿特拉库铵杂质19 | 109717-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 阿特拉库铵杂质19
• 英文名称: (S)-3,4-dimethoxyphenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl-methanol
• 英文别名: (-)-threo-hydroxynorlaudanosine；(S)-(3,4-dimethoxyphenyl)-[(1S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methanol
• CAS: 109717-73-9
• 化学式: C₂₀H₂₅NO₅
• 分子量: 359.422
• InChiKey: KLRIVPGGWAEQKR-PMACEKPBSA-N

物化性质

• 沸点：
  519.3±50.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  阿特拉库铵杂质19 在 氯化亚砜 作用下， 以 水 为溶剂， 生成 (+)-(R)-xylopinine
  参考文献：
  名称：

  Pictet-Spengler Reaction of Biogenic Amines with (2R)-N-Glyoxyloylbornane-10,2-sultam. Enantioselective Synthesis of (S)-(+)-N-Methylcalycotomine and (R)-(+)-Xylopinine

  摘要：

  The Pictet-Spengler reaction of (2R)-N-glyoxyloylbornane-10,2-sultam with dopamine hydrochloride gave the condensation product, which was further converted into (S)-(+)-N)-methylcalycotomine and (R)-(+)-xylopinine of high enantiomeric purity.

  DOI：

  10.3987/com-99-8681
• 作为产物：
  描述：

  methyl (1S)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-6,7-bis(methoxycarbonyloxy)-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 ammonium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 50.0h， 生成 阿特拉库铵杂质19
  参考文献：
  名称：

  Pictet-Spengler Reaction of Biogenic Amines with (2R)-N-Glyoxyloylbornane-10,2-sultam. Enantioselective Synthesis of (S)-(+)-N-Methylcalycotomine and (R)-(+)-Xylopinine

  摘要：

  The Pictet-Spengler reaction of (2R)-N-glyoxyloylbornane-10,2-sultam with dopamine hydrochloride gave the condensation product, which was further converted into (S)-(+)-N)-methylcalycotomine and (R)-(+)-xylopinine of high enantiomeric purity.

  DOI：

  10.3987/com-99-8681

文献信息

• Asymmetric Synthesis of Isoquinoline Alkaloids: (R)- and (S)-2-Ethoxycarbonyl-1-Formyl-6, 7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline as Versatile Precursors
  作者：Zbigniew Czarnocki、David B. Maclean、Walter A. Szarek

  DOI：10.1002/bscb.19860950905

  日期：——

  AbstractA method is described for the preparation of (R)‐ and (S)‐2‐ethoxycarbonyl‐1‐formyl‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline involving a Swerntype oxidation of (R)‐ and (S)‐2‐ethoxycarbonyl‐1‐hydroxymethyl‐6, 7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline (R)‐ and (S)‐2‐(ethoxycarbonyl)calycotomine}. The utility of these aldehydes in asymmetric synthesis of isoquinoline alkaloids has been demonstrated by their conversion into (S)‐ and (R)‐xylopinine, respectively; also, the (R)‐aldehyde has been employed for the synthesis of (8S,14S)‐coralydine.
• 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