2-(2-allyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)-2-methylpropionic acid methyl ester | 1261556-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(2-allyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)-2-methylpropionic acid methyl ester
• 英文别名: methyl 2-(2-allyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)-2-methylpropanoate；Methyl 2-(2-allyl-3-oxo-2,3-dihydro-1h-isoindol-1-yl)-2-methylpropanoate；methyl 2-methyl-2-(3-oxo-2-prop-2-enyl-1H-isoindol-1-yl)propanoate
• CAS: 1261556-95-9
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: VVDZUPRCLOPMNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-allyl-3-hydroxyisoindolin-1-one 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(2-allyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)-2-methylpropionic acid methyl ester
  参考文献：
  名称：

  Synthesis of 3-substituted N-allylisoindolinone derivatives by the acetate method

  摘要：

  A series of N-allylisoindolinone derivatives were prepared by a novel sequential reaction of 2-allyl-3-oxoisoindolin-1-yl acetate with C-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate. The nucleophiles included arenes, alkenes, and active methylene to give 3-substituted N-allylisoindolinone products. This method was applied to synthesize cyclohexane-fused indolizidine alkaloid mimics using Grubbs' catalyst..

  DOI：

  10.1007/s00706-013-1127-z

文献信息

• One-Pot Hydroxy Group Activation/Carbon-Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System
  作者：Alice Devineau、Guillaume Pousse、Catherine Taillier、Jérôme Blanchet、Jacques Rouden、Vincent Dalla

  DOI：10.1002/adsc.201000602

  日期：2010.11.22

  distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′-bi-2-naphthol (BINOL)-derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one-pot Brønsted base-Brønsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.

  提出了一种新的连续两步多催化策略，该策略包括有效的DBU催化的醇的三氯乙酰亚胺化，然后由硅基亲核试剂和CH亲核试剂进行双三氟乙胺（Tf 2 NH）催化的分子间烷基化。三氯乙酰基亚氨酸酯基团的独特特征允许使用弱酸催化剂，例如1,1'-联-2-萘酚（BINOL）衍生的磷酸，指出了对映选择性变体的可能发展。这种前所未有的连续一锅法布朗斯台德碱布朗斯台德酸催化进一步扩大了三氯乙酰亚胺基的合成范围。
• Synthesis of 3-substituted N-allylisoindolinone derivatives by the acetate method
  作者：Ibrahim A. I. Ali

  DOI：10.1007/s00706-013-1127-z

  日期：2014.5

  A series of N-allylisoindolinone derivatives were prepared by a novel sequential reaction of 2-allyl-3-oxoisoindolin-1-yl acetate with C-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate. The nucleophiles included arenes, alkenes, and active methylene to give 3-substituted N-allylisoindolinone products. This method was applied to synthesize cyclohexane-fused indolizidine alkaloid mimics using Grubbs' catalyst..