(S)-3-(2-(2-hydroxyethyl)-5-isopropoxy-4-methoxyphenyl)-7-isopropoxy-8-methoxy-3,4-dihydroisoquinolin-1(2H)-one | 1260522-93-7

• 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
• 英文名称: (S)-3-(2-(2-hydroxyethyl)-5-isopropoxy-4-methoxyphenyl)-7-isopropoxy-8-methoxy-3,4-dihydroisoquinolin-1(2H)-one
• 英文别名: (3S)-3-[2-(2-hydroxyethyl)-4-methoxy-5-propan-2-yloxyphenyl]-8-methoxy-7-propan-2-yloxy-3,4-dihydro-2H-isoquinolin-1-one
• CAS: 1260522-93-7
• 化学式: C₂₅H₃₃NO₆
• 分子量: 443.54
• InChiKey: TTXALVPAGNJVLY-IBGZPJMESA-N

物化性质

• 沸点：
  647.6±55.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-(2-(2-hydroxyethyl)-5-isopropoxy-4-methoxyphenyl)-7-isopropoxy-8-methoxy-3,4-dihydroisoquinolin-1(2H)-one 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化硼 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 4.0h， 生成 左旋千金藤啶碱
  参考文献：
  名称：

  Total Synthesis of (S)-(-)-Stepholidine Using (S)-tert-Butanesulfinylimine

  摘要：

  A new synthetic strategy of (S)-()-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (5)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (S)-(-)-St epholidine was prepared after another 5 steps, with an overall yield of 18.3% and > 98% ee.

  DOI：

  10.3987/com-10-12056
• 作为产物：
  描述：

  4-异丙氧基-3-甲氧基苯甲醛 在 titanium(IV) isopropylate 、 盐酸 、 ammonium hydroxide 、 正丁基锂 、 三聚氯氰 、 草酰氯 、 palladium 10% on activated carbon 、 水 、 氢气 、 三乙胺 、 potassium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， -78.0~30.0 ℃ 、101.33 kPa 条件下， 反应 77.17h， 生成 (S)-3-(2-(2-hydroxyethyl)-5-isopropoxy-4-methoxyphenyl)-7-isopropoxy-8-methoxy-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Total Synthesis of (S)-(-)-Stepholidine Using (S)-tert-Butanesulfinylimine

  摘要：

  A new synthetic strategy of (S)-()-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (5)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (S)-(-)-St epholidine was prepared after another 5 steps, with an overall yield of 18.3% and > 98% ee.

  DOI：

  10.3987/com-10-12056

文献信息

• Total Synthesis of (S)-(-)-Stepholidine Using (S)-tert-Butanesulfinylimine
  作者：Yushe Yang、Liqiang Fu、Chenyu Ling

  DOI：10.3987/com-10-12056

  日期：——

  A new synthetic strategy of (S)-()-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (5)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (S)-(-)-St epholidine was prepared after another 5 steps, with an overall yield of 18.3% and > 98% ee.