2-{3-[(Z)-Hydroxyimino]-3-phenyl-propyl}-isoindole-1,3-dione | 339567-72-5

• 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: 2-{3-[(Z)-Hydroxyimino]-3-phenyl-propyl}-isoindole-1,3-dione
• CAS: 339567-72-5
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: BPTMMVGRVQMLOL-UHFFFAOYSA-N

物化性质

• 沸点：
  495.1±28.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.97
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-{3-[(Z)-Hydroxyimino]-3-phenyl-propyl}-isoindole-1,3-dione 在 吡啶 作用下， 反应 12.0h， 以0.19 g的产率得到1-phenyl-3-(phthalimido)-propan-1-one O-acetyloxime
  参考文献：
  名称：

  Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic amounts of TMSOTf

  摘要：

  The O-phthalimidomethyl trichloroacetimidate (1), as a latent aminomethylating agent, exhibits high electrophilicity towards a variety of C-nucleophiles in the presence of catalytic amounts of TMSOTf and mild reaction conditions. The nucleophiles include aromatics, alkenes and active methylene compounds 2-11 whereby a phthalimidomethyl group could be introduced to give compounds 12-22. Removal of the phthaloyl group gave the respective amines, beta-amino ketones, and beta-amino acids. The O-(trichloroacetamido)methyl trichloroacetimidate (35) was also found to be a good amidomethylating agent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.011
• 作为产物：
  描述：

  O-phthalimidomethyl trichloroacetamidate 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 盐酸羟胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 2-{3-[(Z)-Hydroxyimino]-3-phenyl-propyl}-isoindole-1,3-dione
  参考文献：
  名称：

  Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic amounts of TMSOTf

  摘要：

  The O-phthalimidomethyl trichloroacetimidate (1), as a latent aminomethylating agent, exhibits high electrophilicity towards a variety of C-nucleophiles in the presence of catalytic amounts of TMSOTf and mild reaction conditions. The nucleophiles include aromatics, alkenes and active methylene compounds 2-11 whereby a phthalimidomethyl group could be introduced to give compounds 12-22. Removal of the phthaloyl group gave the respective amines, beta-amino ketones, and beta-amino acids. The O-(trichloroacetamido)methyl trichloroacetimidate (35) was also found to be a good amidomethylating agent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.011