N-Phenoxymethyl-phthalimid | 92498-03-8

• 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: N-Phenoxymethyl-phthalimid
• 英文别名: N-phenoxymethyl-phthalimide；Phthalimidylmethoxybenzene；2-(Phenoxymethyl)isoindole-1,3-dione
• CAS: 92498-03-8
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: XMNDBFBXVMFROO-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  415.6±28.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Phenoxymethyl-phthalimid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以96%的产率得到3-hydroxy-2-(phenoxymethyl)-3H-isoindol-1-one
  参考文献：
  名称：

  N-酰基亚胺离子的分子内芳基化合成异吲哚并[1,3]苯并恶嗪衍生物

  摘要：

  [1,3]与N-氯甲基邻苯二甲酰亚胺5和取代的酚6分三步合成了与3和4异吲哚环化的苯并恶嗪。关键步骤是ω-甲醇内酰胺8和9的酸催化环化反应。

  DOI：

  10.1002/jhet.5570350644
• 作为产物：
  描述：

  N-羟甲基邻苯二甲酰亚胺 在 18-冠醚-6 、 甲基磺酰氟 、 sodium hydride 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 生成 N-Phenoxymethyl-phthalimid
  参考文献：
  名称：

  Selective fluorination of substituted methanols with methanesulfonyl fluoride and cesium fluoride as modified with crown ethers

  摘要：

  DOI：

  10.1016/s0022-1139(00)81966-1

文献信息

• Tunable System for Electrochemical Reduction of Ketones and Phthalimides
  作者：Yaxin Wang、Jianyou Zhao、Tianjiao Qiao、Jian Zhang、Gong Chen

  DOI：10.1002/cjoc.202100508

  日期：2021.12

  Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously

  在此，我们报告了一种高效、可调的系统，用于在室温下电化学还原酮和邻苯二甲酰亚胺，无需化学计量的外部还原剂。通过使用 NaN 3作为电解质和石墨毡作为阴极和阳极，我们能够通过明智地选择溶剂和酸性添加剂，将基材的羰基选择性地还原为醇、频哪醇或亚甲基。反应条件与多种官能团兼容，邻苯二甲酰亚胺可以进行一锅还原环化反应，得到带有吲哚里西啶支架的产物。机理研究表明，反应涉及电子、质子和氢原子的转移。重要的是，N 3 /HN 3 循环作为氢原子穿梭运行，这对于将羰基还原为亚甲基至关重要。
• 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS
  申请人：Koltun Dmitry

  公开号：US20080255161A1

  公开（公告）日：2008-10-16

  The present invention discloses 3-hydroquinazolin-4-one derivatives for use as inhibitors of stearoyl-CoA desaturase. The compounds are useful in treating and/or preventing various human diseases, mediated by stearoyl-CoA desaturase (SCD) enzymes, especially diseases related to abnormal lipid levels, cancer, cardiovascular disease, diabetes, obesity, metabolic syndrome and the like.

  本发明揭示了3-羟基喹唑啉-4-酮衍生物，用作硬脂酰辅酶A去饱和酶的抑制剂。这些化合物在治疗和/或预防由硬脂酰辅酶A去饱和酶（SCD）酶介导的各种人类疾病方面具有用途，特别是与异常脂质水平、癌症、心血管疾病、糖尿病、肥胖、代谢综合征等相关的疾病。
• Activation of Carbon−Oxygen Bonds by Palladium:  Toward a Mild, Catalytic Approach to α-Amino Acid Derivatives
  作者：Yingdong Lu、Bruce A. Arndtsen

  DOI：10.1021/ol7021017

  日期：2007.10.1

  mediated method to induce the carbon-oxygen bond of amide-substituted ethers to undergo addition to palladium is described. The product of this reaction has been crystallographically characterized. This reaction suggests the potential use of such ethers as an alternative to organic halides in palladium catalyzed carbon-carbon bond formation. As an illustration of this potential, this reaction has been used

  描述了路易斯酸介导的方法，该方法诱导酰胺取代的醚的碳-氧键加成到钯上。该反应的产物已经在晶体学上进行了表征。该反应表明在钯催化的碳-碳键的形成中可以潜在地使用这些醚作为有机卤化物的替代物。作为这种潜力的例证，该反应已被用于设计从α-苯氧基酰胺和一氧化碳到α-氨基酸衍生物的温和催化路线。
• Mechanism of hydrolysis of O-imidomethyl derivatives of phenols
  作者：John J. Getz、Richard J. Prankerd、Kenneth B. Sloan

  DOI：10.1021/jo00070a029

  日期：1993.8

  Three series of O-imidomethyl derivatives of para-substituted phenolic compounds were synthesized and their rates of hydrolysis were studied. Saccharin, phthalimide, and succinimide served as the imide portions of the derivatives. Their rates of hydrolysis were found to be first order with respect to hydroxide from pH 7.0 to 10 or 11 and dependent on the acidity (leaving group potential) of both the imide and the phenol portions. The more acidic the imide or the phenol, the faster the rate of hydrolysis. However, the rates of hydrolysis were more sensitive to the acidity of the phenol. Trapping experiments with cyanide also suggested that the phenol anion was functioning as the leaving group in what is apparently an S(N)2 reaction. An amide derivative was found to hydrolyze more slowly than predicted from the analogous imide series and the pK(a) of the amide. This result is apparently due partially to stereoelectronic constraints in the imide series that cause the CH2-O bond to be oriented more nearly perpendicular to the plane of the C (=O)N group and hence more accessible to nucleophilic attack.
• Multimetallic Iridium-Tin (Ir-Sn₃) Catalyst in<i>N</i>-Acyliminium Ion Chemistry: Synthesis of 3-Substituted Isoindolinones<i>via</i>Intra- and Intermolecular Amidoalkylation Reaction
  作者：Arnab Kumar Maity、Sujit Roy

  DOI：10.1002/adsc.201400234

  日期：2014.8.11

  AbstractThe multimetallic iridium‐tritin (Ir‐Sn3) complex [Cp*Ir(SnCl3)2SnCl2(H2O)2}] (1) proved to be a highly effective catalyst towards COH bond activation of γ‐hydroxylactams, leading to a nucleophilic substitution reaction known as the α‐amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer [Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3‐dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3‐substituted isoindolinones and 5‐substituted pyrrolidin‐2‐ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir‐Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ‐hydroxylactam towards the formation of the N‐acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.magnified image