(3S,4R)-(-)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-3-phenyl-1,2,3,4-tetrahydroisoquinoline | 158666-75-2

• 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: (3S,4R)-(-)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-3-phenyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: tert-butyl-[[(3S,4R)-6-methoxy-3-phenyl-1,2,3,4-tetrahydroisoquinolin-4-yl]oxy]-diphenylsilane
• CAS: 158666-75-2
• 化学式: C₃₂H₃₅NO₂Si
• 分子量: 493.721
• InChiKey: ZTCBUYBKGLRYKP-IOWSJCHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R)-(-)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-3-phenyl-1,2,3,4-tetrahydroisoquinoline 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以82%的产率得到(3S,4R)-(+)-4-hydroxy-6-methoxy-3-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  A simple enzymatic synthesis of (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines

  摘要：

  An efficient versatile method is presented for the stereospecific synthesis of (+)-4hydroxy-3-phenyltetrahydroisoquinoline 11 and 12 using (R)-arylcyanohydrins as the chiral starting material. From this asymmetric core, the synthetic process proceeds with development of the S absolute stereochemistry for the phenyl group at C-3 and the R configuration at C-1 of the target heterocycle. As the protective group protocol allows the stereospecific deprotection at C4, (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines have been prepared using this process.

  DOI：

  10.1016/0957-4166(94)80127-4
• 作为产物：
  描述：

  (1S,2R)-(-)-2-(tert-butyldiphenylsilyloxy)-2-(3-methoxyphenyl)-phenylethylamine hydrochloride 在 sodium tetrahydroborate 、 五氯化磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 (3S,4R)-(-)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-3-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  A simple enzymatic synthesis of (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines

  摘要：

  An efficient versatile method is presented for the stereospecific synthesis of (+)-4hydroxy-3-phenyltetrahydroisoquinoline 11 and 12 using (R)-arylcyanohydrins as the chiral starting material. From this asymmetric core, the synthetic process proceeds with development of the S absolute stereochemistry for the phenyl group at C-3 and the R configuration at C-1 of the target heterocycle. As the protective group protocol allows the stereospecific deprotection at C4, (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines have been prepared using this process.

  DOI：

  10.1016/0957-4166(94)80127-4

文献信息

• A simple enzymatic synthesis of (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines
  作者：Imanol Tellitu、Dolores Badía、Esther Domíguez、Francisco J. García

  DOI：10.1016/0957-4166(94)80127-4

  日期：1994.8

  An efficient versatile method is presented for the stereospecific synthesis of (+)-4hydroxy-3-phenyltetrahydroisoquinoline 11 and 12 using (R)-arylcyanohydrins as the chiral starting material. From this asymmetric core, the synthetic process proceeds with development of the S absolute stereochemistry for the phenyl group at C-3 and the R configuration at C-1 of the target heterocycle. As the protective group protocol allows the stereospecific deprotection at C4, (3S,4R)-(+)-4-hydroxy-3-phenyltetrahydroisoquinolines have been prepared using this process.