(3R,1'R)-3-methyl-2-[2-hydroxy-1-(4-benzyloxyphenyl)ethyl]-2,3-dihydro-1H-isoindolin-1-one | 677009-86-8

• 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: (3R,1'R)-3-methyl-2-[2-hydroxy-1-(4-benzyloxyphenyl)ethyl]-2,3-dihydro-1H-isoindolin-1-one
• 英文别名: (3R)-2-[(1R)-2-hydroxy-1-(4-phenylmethoxyphenyl)ethyl]-3-methyl-3H-isoindol-1-one
• CAS: 677009-86-8
• 化学式: C₂₄H₂₃NO₃
• 分子量: 373.452
• InChiKey: LKIRTSWLXMRTMT-HXOBKFHXSA-N

物化性质

• 沸点：
  577.8±50.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,1'R)-3-methyl-2-[2-hydroxy-1-(4-benzyloxyphenyl)ethyl]-2,3-dihydro-1H-isoindolin-1-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以84%的产率得到3(R)-甲基异吲哚啉-1-酮
  参考文献：
  名称：

  A versatile approach for the asymmetric synthesis of 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones

  摘要：

  Based on the use of (R)-p-benzyloxyphenylglycinol (10) as a new oxidatively cleavable chiral auxiliary, a flexible approach to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones via a diastereoselective reductive-alkylation is developed. The oxidative cleavage of the chiral auxiliary by CAN under mild conditions ensured the access to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones with ee at least 92%. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.092
• 作为产物：
  描述：

  (4-benzyloxy)-D-phenylglycine 在 三乙基硅烷 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 (3R,1'R)-3-methyl-2-[2-hydroxy-1-(4-benzyloxyphenyl)ethyl]-2,3-dihydro-1H-isoindolin-1-one
  参考文献：
  名称：

  A versatile approach for the asymmetric synthesis of 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones

  摘要：

  Based on the use of (R)-p-benzyloxyphenylglycinol (10) as a new oxidatively cleavable chiral auxiliary, a flexible approach to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones via a diastereoselective reductive-alkylation is developed. The oxidative cleavage of the chiral auxiliary by CAN under mild conditions ensured the access to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones with ee at least 92%. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.092

文献信息

• A versatile approach for the asymmetric synthesis of 3-alkyl-2,3-dihydro-1H-isoindolin-1-ones
  作者：Ming-De Chen、Xiang Zhou、Ming-Zhu He、Yuan-Ping Ruan、Pei-Qiang Huang

  DOI：10.1016/j.tet.2003.11.092

  日期：2004.2

  Based on the use of (R)-p-benzyloxyphenylglycinol (10) as a new oxidatively cleavable chiral auxiliary, a flexible approach to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones via a diastereoselective reductive-alkylation is developed. The oxidative cleavage of the chiral auxiliary by CAN under mild conditions ensured the access to (R)-3-alkyl-2,3-dihydro-1H-isoindolin-1-ones with ee at least 92%. (C) 2003 Elsevier Ltd. All rights reserved.