N-methylsulfonylphthalimide | 109722-87-4

• 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-methylsulfonylphthalimide
• 英文别名: N-Benzyloxycarbonyl-phthalimid；1,3-dioxo-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester；benzyl 1,3-dioxoisoindole-2-carboxylate
• CAS: 109722-87-4
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: KFEKJLGEEHSLMK-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C(Solv: ethanol (64-17-5))
• 沸点：
  453.8±38.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methylsulfonylphthalimide 在 2-碘苯甲酸 、 potassium carbonate 、 zinc dibromide 作用下， 以 氯仿 、 氯苯 为溶剂， 反应 43.0h， 生成 benzyl 4-methylene-3′,5-dioxo-4,5-dihydro-3H-spiro[furan-2,1′-isoindoline]-2′-carboxylate
  参考文献：
  名称：

  亚甲基内酯和亚甲基内酰胺基螺化合物的不同合成：酰胺基官能化的γ-羟基内酰胺作为细胞毒性N，O-和N，N-Spiro化合物的前体的效用。

  摘要：

  通过使用酰胺基官能化的γ-羟基内酰胺作为常见中间体，已经合成了具有药物吸引力的基于亚甲基内酯和亚甲基内酰胺的螺环化合物。通过在酸性条件下处理中间体，完成了分叉合成两种类型的N，O-螺环化合物的新路线的开发，从而产生了有效的基于细胞毒性亚甲基内酯的螺环化合物。可以通过中间体中间体末端酰胺部分的N-叔丁氧基羰基保护，然后在碱性条件下内酰胺环化，来递送基于亚甲基内酰胺的新的N，N-螺环化合物。

  DOI：

  10.1021/acs.joc.9b02038
• 作为产物：
  描述：

  potassium phtalimide 、 氯甲酸苄酯 以 二氯甲烷 为溶剂， 以76%的产率得到N-methylsulfonylphthalimide
  参考文献：
  名称：

  Synthesis and evaluation of some variants of the Nefkens’ reagent

  摘要：

  A series of N-substituted phthalimides have been prepared in an effort to explore synthetic variants of the Nefkens' reagent. Three N-acylphthalimides [R = -CH3, -CH2CH3, and -C(CH3)(3)] were prepared and employed for the protection of a series of representative amines. In addition, an N-methanesulfonylphthalimide and N-(diethylphosphoryl)phthalimide were also prepared. It was determined that among the phthalimides that were prepared N-propanoylphthalimide was the most effective reagent for the protection reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.066

文献信息

• Development of new catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds via ring opening-asymmetric reclosure of hydroxylactams
  作者：Tetsuya Sengoku、Ayako Miyoshi、Tamaki Tsuda、Toshiyasu Inuzuka、Masami Sakamoto、Masaki Takahashi、Hidemi Yoda

  DOI：10.1016/j.tet.2020.131252

  日期：2020.6

  Catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds is developed. Hydroxylactams prepared from N-carbonyl phthalimides and β-amido functionalized allylboronates underwent ring opening-asymmetric reclosure in the presence of catalytic amounts of MgBr2 and a chiral aminophenol to afford the corresponding N,O-spirocyclic compounds in excellent yields and high enantioselectivities

  开发了基于亚甲基内酰胺的N，O-螺环化合物的催化对映选择性形成。由N-羰基邻苯二甲酰亚胺和β-氨基官能化的烯丙基硼酸酯制备的羟基内酰胺在催化量的MgBr 2和手性氨基苯酚存在下进行开环-不对称重合反应，从而以优异的收率和高对映选择性提供相应的N，O-螺环化合物。
• Use of β-Amido Allylboronate as a Nucleophilic Reagent in Catalytic Amide Allylation of <i>N</i> -Carbonyl Imides
  作者：Tetsuya Sengoku、Yuta Kamiya、Ai Kawakami、Masaki Takahashi、Hidemi Yoda

  DOI：10.1002/ejoc.201701112

  日期：2017.11.2

  This communication describes the utility of β-amido allylboronate as a nucleophile in the catalytic amide allylation of N-carbonyl imides. The reaction of the imide substrates with the boronates has been accomplished by using catalytic zinc bromide and basic additives (ethanol, potassium carbonate and 18-crown 6-ether), affording azaspiro-γ-lactones through a ring opening-reclosure process with yields

  本通讯描述了 β-酰氨基烯丙基硼酸酯在 N-羰基酰亚胺的催化酰胺烯丙基化中作为亲核试剂的用途。通过使用催化溴化锌和碱性添加剂（乙醇、碳酸钾和 18-冠 6-醚）完成酰亚胺底物与硼酸盐的反应，通过开环-重闭过程得到氮杂螺-γ-内酯，产率提高到 100%。这里建立的具有成本效益且易于操作的方法可用于克级合成，而不会显着降低反应效率。
• Catalyst comprising a cyclic imide compound and process for producing organic compounds using the catalyst
  申请人：——

  公开号：US20020128149A1

  公开（公告）日：2002-09-12

  A catalyst includes a cyclic imide compound having an N-substituted cyclic imide skeleton represented by following Formula (I): 1 wherein X is an oxygen atom or a hydroxyl group, and having a solubility parameter of less than or equal to 26 [(MPa) ½ ] as determined by Fedors method. The catalyst may further comprise a metallic compound. By allowing (A) a compound capable of forming a radical to react with (B) a radical scavenging compound in the presence of the catalyst, an addition or substitution reaction product between the compound (A) and the compound (B) or a derivative thereof can be obtained.

  催化剂包括具有由下式（I）表示的N-取代的环状亚酰亚胺骨架的环状亚酰亚胺化合物，其中X是氧原子或羟基，并且具有由Fedors方法确定的溶解度参数小于或等于26 [（MPa）½]。该催化剂还可以包括金属化合物。通过允许（A）能够形成自由基的化合物与（B）自由基清除化合物在催化剂存在的情况下发生反应，可以获得化合物（A）和化合物（B）之间的加成或取代反应产物或其衍生物。
• Versatile Ru‐Photoredox‐Catalyzed Functionalization of Dehydro‐Amino Acids and Peptides
  作者：Tobias Brandhofer、Olga García Mancheño

  DOI：10.1002/cctc.201900446

  日期：2019.8.21

  A versatile photoredox‐catalyzed synthesis of unnatural amino acids and peptides is presented. Commercially available Ru(bpy)3(PF6)2 was efficiently used as visible light photocatalyst in combination with a broad number of different types of radical precursors in the coupling with several dehydrogenated amino acid residues. This method provides new entries to the mild, selective and direct modification

  提出了一种通用的光氧化还原催化的非天然氨基酸和肽的合成方法。在与几个脱氢氨基酸残基偶合的过程中，将市售的Ru（bpy）3（PF 6）2与多种不同类型的自由基前体组合有效地用作可见光光催化剂。该方法为简单和复杂的肽样化合物向具有改进或异常特性的新型结构的温和，选择性和直接修饰提供了新的思路。因此，（氟化）烷基卤化物，芳基磺酰氯或各种N-（酰氧基）邻苯二甲酰亚胺（NHPI酯）与一系列天然和非天然的α，β-脱氢氨基酸和二肽有效反应。而且，该方法的适用性还通过天然存在的肽硫代链丝菌肽的后期功能化来证明。
• Melanocortin receptor-specific compounds
  申请人：Palatin Technologies, Inc.

  公开号：US20040224957A1

  公开（公告）日：2004-11-11

  A melanocortin receptor-specific compound of the general formula of structure I: 1 where X, R 1 , R 2a , R 2b , R 3 , R 4a , R 4b , R 5a and R 5b are as defined in the specification, which compound binds with high affinity to one or more melanocortin receptors and is optionally an agonist, an antagonist, an inverse agonist or an antagonist of an inverse agonist, and may be employed for treatment of one or melanocortin receptor-associated conditions or disorders, and methods for the use of the compounds of the invention.

  一种具有结构I：1的一般式的黑素皮质素受体特异性化合物，其中X、R1、R2a、R2b、R3、R4a、R4b、R5a和R5b如说明书中所定义，该化合物与一个或多个黑素皮质素受体高亲和结合，并可选择性地为激动剂、拮抗剂、逆拮抗剂或逆拮抗剂的拮抗剂，并可用于治疗一个或多个黑素皮质素受体相关疾病或疾病，并且使用该发明化合物的方法。