(-)-(S)-6-methoxy-3-phenyl-3,4-dihydroisoquinolin-1(2H)-one | 208345-54-4

• 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)-6-methoxy-3-phenyl-3,4-dihydroisoquinolin-1(2H)-one
• 英文别名: (S)-(-)-6-methoxy-3-phenyl-3,4-dihydro-1(2H)-isoquinolone；(S)-6-methoxy-3-phenyl-3,4-dihydroisoquinolin-1(2H)-one；(3S)-6-methoxy-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one
• CAS: 208345-54-4
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: NBRLIYHYGMOBPB-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(S)-6-methoxy-3-phenyl-3,4-dihydroisoquinolin-1(2H)-one 在 咪唑 、 dimethyl sulfide borane 、 (-)-(camphorylsulfonyl)oxaziridine 、 sodium hydride 、 lithium diisopropyl amide 作用下， 生成 (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Sulfinimine mediated asymmetric synthesis of 3-substituted-1(2H)-isoquinolones: (3R,4S)-(−)-4-hydroxy-3-phenyltetrahydroisoquinoline

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(98)00506-1
• 作为产物：
  描述：

  (S,E)-N-benzylidene-4-methylbenzenesulfinamide 在 叔丁基锂 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 生成 (-)-(S)-6-methoxy-3-phenyl-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Sulfinimine mediated asymmetric synthesis of 3-substituted-1(2H)-isoquinolones: (3R,4S)-(−)-4-hydroxy-3-phenyltetrahydroisoquinoline

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(98)00506-1

文献信息

• General Enantioselective C−H Activation with Efficiently Tunable Cyclopentadienyl Ligands
  作者：Zhi-Jun Jia、Christian Merten、Rajesh Gontla、Constantin G. Daniliuc、Andrey P. Antonchick、Herbert Waldmann

  DOI：10.1002/anie.201611981

  日期：2017.2.20

  applicable chiral Cp ligand collection (JasCp ligands) with highly variable and adjustable structures. Their modular nature and their amenability to rapid structure variation enabled the efficient discovery of ligands for three enantioselective RhIII‐catalyzed C−H activation reactions, including one unprecedented transformation. This novel approach should enable the discovery of efficient chiral Cp ligands

  环戊二烯基（Cp）配体可有效控制各种过渡金属催化的转化，特别是对映选择性的CH活化。目前只有几种手性Cp配体可用。因此，用于手性Cp配体发现的概念上通用的方法将是无价的，因为它将使得能够发现适用的Cp配体并有效且快速地改变和调节其结构。在这里，我们描述了具有高度可变和可调节结构的结构多样且广泛适用的手性Cp配体集合（JasCp配体）的三步克级合成。它们的模块性质和对快速结构变化的适应性使得能够有效发现三种对映选择性Rh III的配体催化的CH活化反应，包括一种前所未有的转化。这种新颖的方法应该能够发现用于各种进一步对映选择性转化的有效手性Cp配体。
• Chiral Cyclopentadienyl Cobalt(III) Complexes Enable Highly Enantioselective 3d-Metal-Catalyzed C–H Functionalizations
  作者：Kristers Ozols、Yun-Suk Jang、Nicolai Cramer

  DOI：10.1021/jacs.9b02569

  日期：2019.4.10

  The synthesis of a set of cobalt(III)-complexes equipped with trisubstituted chiral cyclopentadienyl ligands is reported, and their steric and electronic parameters are mapped. The application potential of these complexes for asymmetric C-H functionalizations with 3d-metals is shown by the synthesis of dihydroisoquinolones from N-chlorobenzamides with a broad range of alkenes. The transformation proceeds

  报道了一组配备三取代手性环戊二烯基配体的钴 (III) 配合物的合成，并绘制了它们的空间和电子参数。这些配合物在具有 3d 金属的不对称 CH 官能化方面的应用潜力通过从具有广泛烯烃的 N-氯苯甲酰胺合成二氢异喹诺酮类药物来展示。转化过程具有高达 99.5:0.5 er 的出色对映选择性和高区域选择性。对于这种反应类型，观察到的值优于基于铑 (III) 的最佳方法。此外，具有挑战性的底物（如烷基烯烃）也会与高区域选择性和对映选择性反应。
• 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.
• 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.