(3S,4R)-(-)-4-hydroxy-6-methoxy-3-phenyl-3,4-dihydro-1(2H)-isoquinolone | 253308-77-9

• 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
• 英文名称: (3S,4R)-(-)-4-hydroxy-6-methoxy-3-phenyl-3,4-dihydro-1(2H)-isoquinolone
• 英文别名: (3S,4R)-4-hydroxy-6-methoxy-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one
• CAS: 253308-77-9
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: IMUFVLCHLMJVQW-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R)-(-)-4-hydroxy-6-methoxy-3-phenyl-3,4-dihydro-1(2H)-isoquinolone 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3S,4R)-(-)-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
• 作为产物：
  描述：

  (S)-N-[(S)-[(1R)-6-methoxy-3-oxo-1H-2-benzofuran-1-yl]-phenylmethyl]-4-methylbenzenesulfinamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以85%的产率得到(3S,4R)-(-)-4-hydroxy-6-methoxy-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

• Asymmetric Synthesis of 4-Hydroxy-3-phenyltetrahydroisoquinoline Derivatives Using Enantiopure Sulfinimines (<i>N</i>-Sulfinyl Imines)
  作者：Franklin A. Davis、Yemane W. Andemichael

  DOI：10.1021/jo991119x

  日期：1999.11.1

  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.