(3S,1'S)-2-(2-hydroxyl-1-phenylethyl)-3-methylisoindolin-1-one

• 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: (3S,1'S)-2-(2-hydroxyl-1-phenylethyl)-3-methylisoindolin-1-one
• 英文别名: (3S)-2-[(1S)-2-hydroxy-1-phenylethyl]-3-methyl-3H-isoindol-1-one
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: CKDXLXJMVKZAFW-BLLLJJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3S,9bR)-9b-methyl-3-phenyl-2,3-dihydro-[1,3]oxazolo[2,3-a]isoindol-5-one 在 三乙基硅烷 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(3S,1'S)-2-(2-hydroxyl-1-phenylethyl)-3-methylisoindolin-1-one
  参考文献：
  名称：

  A highly diastereoselective synthesis of 3-substituted isoindolin-1-one dericatives

  摘要：

  A highly diastereoselective method for the synthesis of 3-substituted isoindolin-1-ones has been developed through application of a tricyclic lactam substrate as an N-acyliminium ion precursor. Ring-opening of the tricyclic lactam with triethylsilane as hydride source generates the targets with up to exclusive levels of diastereoselectivity. This approach compliments that reported in the preceding paper. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)80042-7

文献信息

• Bis-Lewis acids-catalyzed highly diastereoselective one-pot reductive dehydroxylation of chiral N,O-acetals
  作者：Li-Jiao Jiang、Bo Teng、Jian-Feng Zheng、Jian-Liang Ye、Pei-Qiang Huang

  DOI：10.1016/j.tet.2009.11.003

  日期：2010.1

  A one-pot and highly diastereoselective method for the reductive dehydroxylation of three classes of heterocyclic N,O-acetals with general structure 4 is reported. The method features a 'two in one' concept, namely, by synergetic action of two complementary Lewis acids (BF.OEt2 and TiCl4), the bicyclic or tricyclic oxazololactams 5 were formed in situ and reductively cleaved to give the corresponding lactams 6 in a high-yielding and highly diastereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.
• A highly diastereoselective synthesis of 3-substituted isoindolin-1-one dericatives
  作者：Steven M. Allin、Christopher J. Northfield、Michael I. Page、Alexandra M.Z. Slawin

  DOI：10.1016/s0040-4039(98)80042-7

  日期：1999.1

  A highly diastereoselective method for the synthesis of 3-substituted isoindolin-1-ones has been developed through application of a tricyclic lactam substrate as an N-acyliminium ion precursor. Ring-opening of the tricyclic lactam with triethylsilane as hydride source generates the targets with up to exclusive levels of diastereoselectivity. This approach compliments that reported in the preceding paper. (C) 1998 Elsevier Science Ltd. All rights reserved.