7-hydroxy-6-((S)-2-methoxymethylpyrrolidin-1-yl)-7-(4-methoxyphenyl)-6,7-dihydro-1,3-dioxolo-[4,5-f]-5H-isoindol-5-one | 1131192-64-7

• 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: 7-hydroxy-6-((S)-2-methoxymethylpyrrolidin-1-yl)-7-(4-methoxyphenyl)-6,7-dihydro-1,3-dioxolo-[4,5-f]-5H-isoindol-5-one
• 英文别名: 7-hydroxy-6-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-7-(4-methoxyphenyl)-[1,3]dioxolo[4,5-f]isoindol-5-one
• CAS: 1131192-64-7
• 化学式: C₂₂H₂₄N₂O₆
• 分子量: 412.442
• InChiKey: HJUBLMWESHREQX-UEDXYCIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-hydroxy-6-((S)-2-methoxymethylpyrrolidin-1-yl)-7-(4-methoxyphenyl)-6,7-dihydro-1,3-dioxolo-[4,5-f]-5H-isoindol-5-one 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(R)-6-((S)-2-methoxymethylpyrrolidin-1-yl)-7-(4-methoxyphenyl)-6,7-dihydro-1,3-dioxolo[4,5-f]isoindol-5-one
  参考文献：
  名称：

  A conceptually new approach to the asymmetric synthesis of 3-aryl and alkyl poly-substituted isoindolinones

  摘要：

  A conceptually new and efficient asymmetric synthesis of C-3 arylated or alkylated poly-substituted iso-indolinones is reported. The key step is the diastereoselective reduction of an N-acylhydrazonium species derived from the previously assembled corresponding hydroxyl derivative hearing the (S)-2-methoxymethylpyrrolidine (SMP) auxiliary. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.021
• 作为产物：
  描述：

  N-(6-iodo-1,3-benzodioxole-5-carbonyl)-4-methoxy-N-((S)-2-methoxymethylpyrrolidin-1-yl)benzamide 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 以84%的产率得到7-hydroxy-6-((S)-2-methoxymethylpyrrolidin-1-yl)-7-(4-methoxyphenyl)-6,7-dihydro-1,3-dioxolo-[4,5-f]-5H-isoindol-5-one
  参考文献：
  名称：

  A conceptually new approach to the asymmetric synthesis of 3-aryl and alkyl poly-substituted isoindolinones

  摘要：

  A conceptually new and efficient asymmetric synthesis of C-3 arylated or alkylated poly-substituted iso-indolinones is reported. The key step is the diastereoselective reduction of an N-acylhydrazonium species derived from the previously assembled corresponding hydroxyl derivative hearing the (S)-2-methoxymethylpyrrolidine (SMP) auxiliary. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.021

文献信息

• A conceptually new approach to the asymmetric synthesis of 3-aryl and alkyl poly-substituted isoindolinones
  作者：Eric Deniau、Axel Couture、Pierre Grandclaudon

  DOI：10.1016/j.tetasy.2008.11.021

  日期：2008.12

  A conceptually new and efficient asymmetric synthesis of C-3 arylated or alkylated poly-substituted iso-indolinones is reported. The key step is the diastereoselective reduction of an N-acylhydrazonium species derived from the previously assembled corresponding hydroxyl derivative hearing the (S)-2-methoxymethylpyrrolidine (SMP) auxiliary. (C) 2008 Elsevier Ltd. All rights reserved.