(3R,1'R)-3-n-propyl-2-[2-hydroxy-1-(4-benzyloxyphenyl)ethyl]-2,3-dihydro-1H-isoindolin-1-one | 677009-88-0

• 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-n-propyl-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-propyl-3H-isoindol-1-one
• CAS: 677009-88-0
• 化学式: C₂₆H₂₇NO₃
• 分子量: 401.505
• InChiKey: OTKSLHBMUOIQMP-RPBOFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 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-n-propyl-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86%的产率得到(R)-n-propyl-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
• 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-n-propyl-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.