(3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone | 208345-57-7

• 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: (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone
• 英文别名: (3R,4S)-4-[tert-butyl(diphenyl)silyl]oxy-6-methoxy-2-methyl-3-phenyl-3,4-dihydroisoquinolin-1-one
• CAS: 208345-57-7
• 化学式: C₃₃H₃₅NO₃Si
• 分子量: 521.731
• InChiKey: ZZDBEVKJJYEANN-JSOSNVBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone 在 dimethyl sulfide borane 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 (3R,4S)-(-)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Asymmetric Synthesis of 4-Hydroxy-3-phenyltetrahydroisoquinoline Derivatives Using Enantiopure Sulfinimines (N-Sulfinyl Imines)

  摘要：

  Addition of lateral lithiated amides and phthalide anions to enantiopure sulfinimines (N-sulfinyl imines) represents a new approach for the asymmetric synthesis of 3-substituted isoquinolones and 3-substituted 4-hydroxy isoquinolones, respectively, important chiral building blocks for isoquinoline alkaloid synthesis. In one example 3-phenylisoquinolone (-)-15b was prepared in >95% ee by treatment of amide ion 10b with sulfinimine (S)-(+)-11 and subsequent deprotection of the N-sulfinyl auxiliary and cyclization. Oxaziridine-mediated hydroxylation of the anion of 16 afforded 4-hydroxy isoquinolone 19, which was transformed into 4-hydroxy-3-phenyltetrahydroisoquinoline (-)-22. In another approach 22 was prepared more directly by addition of phthalide ion 26 to (S)(+)-11, creating the two stereogenic centers simultaneously. The selectivity proved to be highly counterion dependent.

  DOI：

  10.1021/jo991119x
• 作为产物：
  描述：

  (S_S,S)-(+)-N-[1-phenyl-2-(5-methoxy-2-N,N-diethylbenzamido)ethyl]-p-toluenesulfinamide 在 咪唑 、 (camphorylsulfonyl)oxaziridine 、 叔丁基锂 、 sodium hydride 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 6.83h， 生成 (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone
  参考文献：
  名称：

  Asymmetric Synthesis of 4-Hydroxy-3-phenyltetrahydroisoquinoline Derivatives Using Enantiopure Sulfinimines (N-Sulfinyl Imines)

  摘要：

  Addition of lateral lithiated amides and phthalide anions to enantiopure sulfinimines (N-sulfinyl imines) represents a new approach for the asymmetric synthesis of 3-substituted isoquinolones and 3-substituted 4-hydroxy isoquinolones, respectively, important chiral building blocks for isoquinoline alkaloid synthesis. In one example 3-phenylisoquinolone (-)-15b was prepared in >95% ee by treatment of amide ion 10b with sulfinimine (S)-(+)-11 and subsequent deprotection of the N-sulfinyl auxiliary and cyclization. Oxaziridine-mediated hydroxylation of the anion of 16 afforded 4-hydroxy isoquinolone 19, which was transformed into 4-hydroxy-3-phenyltetrahydroisoquinoline (-)-22. In another approach 22 was prepared more directly by addition of phthalide ion 26 to (S)(+)-11, creating the two stereogenic centers simultaneously. The selectivity proved to be highly counterion dependent.

  DOI：

  10.1021/jo991119x

文献信息

• Sulfinimine mediated asymmetric synthesis of 3-substituted-1(2H)-isoquinolones: (3R,4S)-(−)-4-hydroxy-3-phenyltetrahydroisoquinoline
  作者：Franklin A. Davis、Yemane W. Andemichael

  DOI：10.1016/s0040-4039(98)00506-1

  日期：1998.5

  A general approach to enantiomerically pure 3-substituted-1 (2H)-isoquinolones is illustrated by the addition of lateral lithiated amide 7 to sulfinimine 5. Isoquinolone 8 is readily transformed into (3R,4S)-(-)-4-hydroxy-3-phenyltetrahydroisoquinoline 15 via hydroxylation and reduction. (C) 1998 Elsevier Science Ltd. All rights reserved.