(1'S)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one | 929206-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (1'S)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one
• 英文别名: 3-hydroxy-2-((S)-1- phenylethyl)isoindolin-1-one；3-hydroxy-2-[(1S)-1-phenylethyl]-3H-isoindol-1-one
• CAS: 929206-57-5
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: KMTCRDRWKJLWTR-VPHXOMNUSA-N

物化性质

• 沸点：
  445.0±45.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1'S)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one 在 bismuth(lll) trifluoromethanesulfonate 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 3(R)-2-(1(S)-phenylethyl)isoindolin-1-one
  参考文献：
  名称：

  Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst

  摘要：

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).

  DOI：

  10.1021/jo062077x
• 作为产物：
  描述：

  (S)(-)-alpha-苯乙基邻苯二甲酰亚胺 在 甲醇 、 sodium tetrahydroborate 作用下， 生成 (1'S)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one
  参考文献：
  名称：

  DAST 介导的 N-取代 3-烷氧基异吲哚酮的制备

  摘要：

  3-烷氧基-2-苯基乙基异吲哚啉酮可以通过相应的羟基内酰胺与二乙氨基三氟化硫（DAST）在一系列醇的存在下反应来方便地制备。DAST 介导的反应不会导致任何反应物氟化，而是将衍生自反应物醇的烷氧基顺利安装在杂环的苄基位置上。中心起始羟基内酰胺底物由相应的手性邻苯二甲酰亚胺、2-((S)-1-苯基乙基)isoindoline-1,3-二酮通过使用铝汞齐或硼氢化钠选择性还原制备。将所得羟基内酰胺的非对映混合物用于 DAST 烷氧基化反应，并与使用质子酸樟脑磺酸的更常规的烷氧基化方法进行比较。

  DOI：

  10.24820/ark.5550190.p010.809

文献信息

• One-pot three-component highly diastereoselective synthesis of isoindolin-1-one-3-phosphonates under solvent and catalyst free-conditions
  作者：José Luis Viveros-Ceballos、Carlos Cativiela、Mario Ordóñez

  DOI：10.1016/j.tetasy.2011.08.003

  日期：2011.7

  The one-pot three-component reaction of 2-formylbenzoic acid with (S)- and (R)-methylbenzylamine and dimethyl phosphite (Kabachnik-Fields reaction) proceeded in short reaction times under solvent and catalyst free-conditions to afford the corresponding (3R,1'S)- and (3S,1'R)-isoindolin-1-one-3-phosphonates 3, respectively, in good yield and with high diastereoselectivity (95:5 dr). The use of a solvent decreases the diastereoselectivity and slows the reaction rate. The reaction rate was also influenced by CO2H functionality through protonation of the imine intermediate. The absolute configuration at the new stereogenic center was determined by X-ray crystal analysis, and a mechanism was proposed to explain the high diastereoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.
• Access to the New Isoindolo[1,3]benzothiazocinones via the Combination of N-Acyliminium Chemistry and Friedel-Crafts Type π-Cyclization
  作者：Adam Daïch、Armelle Cul、Bernard Decroix、Gérard Sanz、Luc Van Hijfte

  DOI：10.3987/com-04-s(p)18

  日期：——
• Studies on (1S)-N-(1-Phenylethyl)- phthalimide: Synthesis of Both Chiral Spiro Indane and Benzazepine Derivatives
  作者：Adam Daïch、Abderrahim Chihab-Eddine、Abderrahim Jilale、Bernard Decroix

  DOI：10.3987/com-02-s(m)43

  日期：——