methyl 1,3-dioxoisoindoline-5-carboxylate | 56720-83-3

• 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: methyl 1,3-dioxoisoindoline-5-carboxylate
• 英文别名: 4-carbomethoxyphthalimide；1,3-dioxo-1,3-dihydro-isoindole-5-carboxylic acid methyl ester；4-Methoxycarbonylphthalimid；Methyltrimellitatimid；methyl 1,3-dioxoisoindole-5-carboxylate
• CAS: 56720-83-3
• 化学式: C₁₀H₇NO₄
• mdl: MFCD00455850
• 分子量: 205.17
• InChiKey: JRFHQEZVUKIDMX-UHFFFAOYSA-N

物化性质

• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1,3-dioxoisoindoline-5-carboxylate 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 methyl 5,11-dioxo-6a,7,8,9-tetrahydro-6H-pyrrolo[1,2-b][2]benzazepine-3-carboxylate
  参考文献：
  名称：

  Photochemical additions of alkenes to phthalimides. Mechanistic investigations on the stereochemistry of alkene additions and the effect of aryl substituents on the regiochemistry of alkene additions

  摘要：

  DOI：

  10.1021/jo00166a009
• 作为产物：
  描述：

  1,3-二氢-1,3-二氧代异苯并呋喃-5-羧酸甲酯 在 尿素 作用下， 以 xylene 为溶剂， 反应 20.0h， 生成 methyl 1,3-dioxoisoindoline-5-carboxylate
  参考文献：
  名称：

  Photochemical additions of alkenes to phthalimides. Mechanistic investigations on the stereochemistry of alkene additions and the effect of aryl substituents on the regiochemistry of alkene additions

  摘要：

  DOI：

  10.1021/jo00166a009

文献信息

• Compounds and methods for inducing chondrogenesis
  申请人：Schultz Peter

  公开号：US09464065B2

  公开（公告）日：2016-10-11

  The present invention provides compounds and compositions for the amelioration of arthritis and joint injuries by inducing mesenchymal stem cells into chondrocytes.

  本发明提供了一种通过诱导间充质干细胞转化为软骨细胞来改善关节炎和关节损伤的化合物和组合物。
• Rhodium(CAAC)‐Catalyzed Arene Hydrogenation of Benzo‐Fused <i>N</i> ‐Heterocycles to Saturated Building Blocks with an all‐ <i>cis</i> Configuration
  作者：Christian H. Schiwek、Simone Stegbauer、Thomas Pickl、Thorsten Bach

  DOI：10.1002/adsc.202200582

  日期：2022.10.4

  and heterocyclic building blocks can be readily obtained by the hydrogenation of aromatic carbo- and heterocycles. Although a variety of methods have been established to accomplish this transformation for simple arenes, the hydrogenation of aromatic N-heterocycles is less explored. We herein report a diastereoselective arene hydrogenation which was applied to an array of benzo-fused N-heterocycles. A

  饱和碳环和杂环结构单元可以很容易地通过芳族碳环和杂环的氢化获得。尽管已经建立了多种方法来完成简单芳烃的这种转化，但对芳族N-杂环的氢化研究较少。我们在此报告了一种非对映选择性芳烃氢化，该氢化作用应用于一系列苯并稠合的N-杂环。在铑络合物Cy (CAAC)Rh(cod)Cl的存在下，通过氢化得到总共 48 个饱和杂环，产率为 72-98%，具有中到高的非对映选择性，氢原子呈全顺式。安排。对官能团的高耐受性能够形成有价值的饱和产物，这为进一步衍生化提供了起点。
• METHOD FOR PRODUCING ORGANIC COMPOUND AND METHOD FOR DECOMPOSING COMPOUND HAVING DICARBOXYIMIDE SKELETON
  申请人：DAICEL CHEMICAL INDUSTRIES, LTD.

  公开号：EP1870394A1

  公开（公告）日：2007-12-26

  It is desirable to provide a method for easily removing catalyst-derived impurities from a product of a reaction by the catalysis of a compound having a dicarboximide skeleton and thereby efficiently yielding a target compound with high purity. Disclosed is a method for producing an organic compound through a reaction of a substrate in the presence of a catalyst, the catalyst including a compound having a dicarboximide skeleton represented by following Formula (i): wherein R represents hydrogen atom or a hydroxyl-protecting group. The method includes the step of treating a reaction product with hot water so as to decompose and remove an impurity derived from the catalyst. The temperature of the hot water is preferably 100°C or higher.

  希望提供一种方法，通过具有二甲酰亚胺骨架的化合物的催化作用，轻松去除反应产物中的催化剂衍生杂质，从而高效地获得高纯度的目标化合物。 本发明公开了一种在催化剂存在下通过底物反应生产有机化合物的方法，催化剂包括具有二甲酰亚胺骨架的化合物，其代表式如下式(i)： 其中 R 代表氢原子或羟基保护基团。该方法包括用热水处理反应产物的步骤，以便分解和除去来自催化剂的杂质。热水的温度最好为 100℃或更高。
• Coyle, John D.; Smart Lesley E.; Challiner, John F., Journal of the Chemical Society. Perkin transactions I, 1985, p. 121 - 130
  作者：Coyle, John D.、Smart Lesley E.、Challiner, John F.、Haws, Edmud J.

  DOI：——

  日期：——
• Novel and Efficient Azomethine Ylide Forming Photoreactions of N-(Silylmethyl)phthalimides and Related Acid and Alcohol Derivatives
  作者：Ung Chan Yoon、Dong Uk Kim、Chan Woo Lee、Young Sun Choi、Yean-Jang Lee、Herman L. Ammon、Patrick S. Mariano

  DOI：10.1021/ja00115a004

  日期：1995.3

  An investigation of the photochemistry of N-(silylmethyl)phthalimides and related alpha-phthaloylacetic acids and 2-phenylethanol derivatives has uncovered new excited state processes resulting in the formation of azomethine ylide intermediates. Irradiation of N-[(trimethylsilyl)methyl]phthalimide in MeCN promotes C to O silyl transfer to generate the corresponding azomethine ylide which is efficiently trapped by reaction with water to yield the N-methylphthalimide or by dipolar cycloaddition with acetone, methyl acrylate, or acrylonitrile. Cycloadditions with the latter two dipolarophiles are both regioselective and endo-stereoselective. These processes can be triplet photosensitized by use of acetophenone. The related N-[(trimethylsilyl)methyl]-1,8-naphthalimide reacts in a similar manner upon irradiation in MeCN solutions containing the dipolarophiles methyl acrylate and acrylonitrile to produce cycloadducts which undergo spontaneous elimination of TMSOH, yielding alpha,beta-unsaturated ester or nitrile products. The ylide formed by irradiation of the (silylmethyl)phthalimide is trapped in a stereospecific (retention) manner by the dipolarophiles trans-hex-4-en-3-one, dimethyl maleate, and dimethyl fumarate. The effect of aryl ring substitution on the regiochemical course of the photoinduced C to O silyl migration process was probed by use of the 4-methoxy- and 4-carbomethoxyl-N-(silylmethyl)phthalimides. Irradiation of the former substance in an MeCN solution containing acrylonitrile gives rise to a single adduct whose structure suggests that silyl migration to oxygen of the carbonyl meta to the OMe substituent is highly favored. In contrast, the 4-carbomethoxyphthalimide is converted under these conditions to a mixture of regioisomeric adducts. Thus, silyl migration in the excited state of this substance is nonselective. In accord with hints found in earlier observations made by Kanaoka (Chem. Pharm. Bull. 1982, 30, 1263), N-phthalimide derivatives of the alpha-amino acids glycine, alanine, and phenylalanine undergo similar ylide forming photoreactions upon irradiation in MeCN solutions. The azomethine ylides produced by photodecarboxylation of these substances are efficiently trapped by dipolarophiles, and the overall photoreactions starting with the alanine and phenylalanine derivatives are highly stereoselective. Finally, the N-phthalimide derivative of 2-amino-1-phenylethanol also is transformed to a related ylide upon irradiation in MeCN. The nature, regiochemical and stereochemical course, and mechanistic interpretation of these new azomethine ylide forming photoreactions are discussed in this publication.