(S)-6,7-dimethoxy-3-tert-butyldimethylsiloxymethyl-3,4-dihydroisoquinoline | 173377-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: (S)-6,7-dimethoxy-3-tert-butyldimethylsiloxymethyl-3,4-dihydroisoquinoline
• 英文别名: tert-butyl-[[(3S)-6,7-dimethoxy-3,4-dihydroisoquinolin-3-yl]methoxy]-dimethylsilane
• CAS: 173377-04-3
• 化学式: C₁₈H₂₉NO₃Si
• 分子量: 335.519
• InChiKey: VHIHWMQBRPGVIQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-6,7-dimethoxy-3-tert-butyldimethylsiloxymethyl-3,4-dihydroisoquinoline 以 二氯甲烷 为溶剂， 反应 71.0h， 生成 allo-(1R,3S,12R,17R)-7,8-dimethoxy-3-<(tert-butyldimethylsiloxy)methyl>13,14-didehydro-18-oxoberbane
  参考文献：
  名称：

  An efficient asymmetric synthesis of allo- and pseudo-7,8-dimethoxyberbane systems through tin-mediated three component coupling

  摘要：

  Three component coupling reactions of chiral 3-substituted 6,7-dimethoxy-3,4-dihydroisoquinoline with allylic tin reagents and unsaturated acid chlorides followed by intramolecular Diels-Alder reactions afford allo- and pseudo-7,8-dimethoxyberbane systems in high diastereomeric excess.

  DOI：

  10.1016/0957-4166(96)00027-4
• 作为产物：
  描述：

  methyl (S)‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylate 在 咪唑 、 氢氧化钾 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 四丁基碘化铵 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 (S)-6,7-dimethoxy-3-tert-butyldimethylsiloxymethyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  An efficient asymmetric synthesis of allo- and pseudo-7,8-dimethoxyberbane systems through tin-mediated three component coupling

  摘要：

  Three component coupling reactions of chiral 3-substituted 6,7-dimethoxy-3,4-dihydroisoquinoline with allylic tin reagents and unsaturated acid chlorides followed by intramolecular Diels-Alder reactions afford allo- and pseudo-7,8-dimethoxyberbane systems in high diastereomeric excess.

  DOI：

  10.1016/0957-4166(96)00027-4

文献信息

• High 1,3-Asymmetric Induction in Addition of Allylic Tin Reagents to Chiral 3-Substituted 3,4-Dihydroisoquinolines Activated by Acyl Chlorides
  作者：Bunpei Hatano、Yoshikazu Haraguchi、Sinpei Kozima、Ryohei Yamaguchi

  DOI：10.1246/cl.1995.1003

  日期：1995.11

  Nucleophilic addition reactions of allylic tin reagents to chiral 3-substituted 3,4-dihydroisoquinolines activated by acyl chlorides afford anti 1,3-disubstituted 1,2,3,4-tetrahydroisoquinolines stereoselectively through high 1,3-asymmetric induction.

  烯丙基锡试剂与酰氯活化的手性 3-取代 3,4-二氢异喹啉的亲核加成反应通过高 1,3-不对称诱导立体选择性地提供抗 1,3-二取代 1,2,3,4-四氢异喹啉。
• An efficient asymmetric synthesis of allo- and pseudo-7,8-dimethoxyberbane systems through tin-mediated three component coupling
  作者：Yoshikazu Haraguchi、Sinpei Kozima、Ryohei Yamaguchi

  DOI：10.1016/0957-4166(96)00027-4

  日期：1996.2

  Three component coupling reactions of chiral 3-substituted 6,7-dimethoxy-3,4-dihydroisoquinoline with allylic tin reagents and unsaturated acid chlorides followed by intramolecular Diels-Alder reactions afford allo- and pseudo-7,8-dimethoxyberbane systems in high diastereomeric excess.