N-benzyl-4-nitrophthalimide | 60283-84-3

• 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: N-benzyl-4-nitrophthalimide
• 英文别名: 4-nitro-N-benzylphthalimide；4-Nitro-N-benzylphthalimid；2-benzyl-5-nitroisoindole-1,3-dione；2-benzyl-5-nitroisoindoline-1,3-dione；2-Benzyl-5-nitro-isoindolin-1,3-dion
• CAS: 60283-84-3
• 化学式: C₁₅H₁₀N₂O₄
• 分子量: 282.255
• InChiKey: GEJBNUCMDKIJRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-nitrophthalimide 在 三氟甲磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 S-ethyl 5-(2-benzyl-5-nitro-3-oxoisoindolin-1-yl)-2-methyl-4-phenylfuran-3-carbothioate
  参考文献：
  名称：

  通过级联α-氧代酮二硫缩醛与异吲哚啉-1,3-二酮衍生的炔丙基醇的级联反应获得多取代的呋喃-3-碳硫酸酯

  摘要：

  据报道，布朗斯台德（Brønsted）酸促进了前所未有的正式（3 + 2）环化策略，用于合成多取代呋喃3-硫代碳酸盐。该转化代表以级联方式作为1，3-双亲核体的α-氧代烯酮二硫缩醛的第一次区域选择性环化。异吲哚啉-1,3-二酮衍生的炔丙醇的选择对于炔烃型双亲电子试剂和1,3-双亲核试剂在无金属条件下的罕见环合反应模式至关重要。进一步研究了合成的规模化和合成产物的一些有趣的转化。根据实验观察结果，提出了一种类似于Nazarov的环化方法用于闭环过程。

  DOI：

  10.1021/acs.joc.8b00401
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 硫酸 、 硝酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 生成 N-benzyl-4-nitrophthalimide
  参考文献：
  名称：

  A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors

  摘要：

  Several members of a new family of non-sugar-type alpha-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast alpha-glycosidase and rat intestinal alpha-glycosidase. Almost all the compounds had strong inhibitory activities against yeast alpha-glycosidase. Regarding rat intestinal alpha-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal alpha-amylase. Structure-activity relationship studies indicated that 5-(p-toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the alpha-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.011

文献信息

• Palladium-Catalyzed One-Step Synthesis of Isoindole-1,3-diones by Carbonylative Cyclization of <i>o</i>-Halobenzoates and Primary Amines
  作者：Shilpa A. Worlikar、Richard C. Larock

  DOI：10.1021/jo800936h

  日期：2008.9.19

  The palladium-catalyzed aminocarbonylation of o-halobenzoates produces 2-substituted isoindole-1,3-diones in good yields. This methodology provides a good one-step approach to this important class of heterocycles and tolerates a variety of functional groups, including methoxy, alcohol, ketone, and nitro groups.

  邻卤代苯甲酸酯的钯催化氨基羰基化反应以良好的收率生成 2-取代的异吲哚-1,3-二酮。该方法为这一类重要的杂环化合物提供了一种良好的一步法，并且可以耐受多种官能团，包括甲氧基、醇、酮和硝基。
• [EN] A PROCESS FOR PREPARING 5-PHENOXY-1(3H)ISOBENZOFURANONE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 5-PHÉNOXY-1(3H) ISOBENZOFURANONE
  申请人：KINGCHEM LIFE SCIENCE LLC

  公开号：WO2018140186A1

  公开（公告）日：2018-08-02

  The disclosure provides a simple and efficient method for producing a compound of Formula I. The method includes treating an N-substitututed-4-nitro-phthalimide of Formula VII with sodium or potassium phenoxide to form an N-substituted-4-phenoxy-phthalimide of Formula VIII and then treating the N-substituted-4-phenoxy-phthalimide of Formula VIII with zinc in the presence of a base to give 5-phenoxy- l(3H)-isobenzofuranone of Formula I, its isomer of 6-phenoxy- l (3H)-isobenzofuranone of Formula la, and alkyl amine or aryl amine NH2R (Formula IX)

  该公开提供了一种简单高效的方法，用于制备化合物I的方法。该方法包括将式VII的N-取代-4-硝基邻苯二甲酰亚胺与钠或钾苯酚处理，形成式VIII的N-取代-4-苯氧基邻苯二甲酰亚胺，然后在碱存在下将式VIII的N-取代-4-苯氧基邻苯二甲酰亚胺与锌处理，得到式I的5-苯氧基-1(3H)-异苯并呋喃酮，其异构体6-苯氧基-1(3H)-异苯并呋喃酮和烷基胺或芳基胺NH2R（式IX）。
• Colorimetric detection of achiral anions and chiral carboxylates by a chiral thiourea—phthalimide dyad
  作者：Axel G. Griesbeck、Sebastian Hanft、Yrene Díaz Miara

  DOI：10.1039/c0pp00175a

  日期：2010.10

  The chiral chemosensor 1, based on a thiourea-activated phthalimide, is available by four reaction steps from 4-nitrophthalimide. 1 detects fluoride, chloride, acetate, and dihydrogen phosphate anions by changes in UV-vis absorption. Fluoride in excess induces deprotonation whereas the other anions show only complex formation in the ground state. 1H-NMR studies confirm the formation of these H-bonded complexes and the fluoride-induced receptor deprotonation in the recognition process. Moderate chiral recognition was observed for sodium d/L-lactate with Kass(d)/Kass(L) = 1.93.

  手性化学传感器 1 基于硫脲激活的邻苯二甲酰亚胺，由 4-硝基邻苯二甲酰亚胺通过四个反应步骤获得。 1 通过紫外-可见光吸收的变化检测氟化物、氯化物、乙酸盐和磷酸二氢阴离子。过量的氟化物会引起去质子化，而其他阴离子仅在基态下显示出复杂的形成。 1H-NMR 研究证实了这些氢键复合物的形成以及识别过程中氟化物诱导的受体去质子化。 d/L-乳酸钠观察到中等手性识别，Kass(d)/Kass(L) = 1.93。
• Novel Synthesis and Characterization of <i>N</i>‐Substituted‐calix[4]azacrown Derivatives
  作者：Zhi‐Qiang Shi、Ya‐Qing Feng、Na Song、He‐Wen Wang

  DOI：10.1080/00397910701845878

  日期：2008.2.1

  Abstract Novel calix[4]azacrown derivatives from the reaction between calix[4]amidocrown and the different N‐(4‐bromoacetamidephthalimido)alkanes derivatives, which may be useful intemediate compounds of pseudorotaxane, have been synthesized and structurally characterized by IR, 1H NMR, 13C NMR, MS, and elemental analyses. From their analysis data, it was found that compounds 6a–d adopted a cone conformation

  摘要 杯[4]酰胺冠与不同的N-(4-溴乙酰胺邻苯二甲酰亚胺)烷烃衍生物反应合成了新型杯[4]氮杂冠衍生物，这些衍生物可能是假轮烷的有用中间体，已通过IR、1H NMR进行结构表征。 、13C NMR、MS 和元素分析。从他们的分析数据中，发现化合物 6a-d 采用锥形构象。
• Process for preparing 5-phenoxy-1(3)isobenzofuranone
  申请人：KINGCHEM LIFE SCIENCE LLC

  公开号：US10611745B2

  公开（公告）日：2020-04-07

  The disclosure provides a simple and efficient method for producing a compound of Formula I. The method includes treating an N-substituted-4-nitro-phthalimide of Formula VII with sodium or potassium phenoxide to form an N-substituted-4-phenoxy-phthalimide of Formula VIII and then treating the N-substituted-4-phenoxy-phthalimide of Formula VIII with, for example zinc, in the presence of a base to give 5-phenoxy-1(3H)-isobenzofuranone of Formula I, its isomer of 6-phenoxy-1 (3H)-isobenzofuranone of Formula Ia, and alkyl amine or aryl amine NH2R (Formula IX)

  本公开提供了一种生产式 I 化合物的简单而有效的方法。该方法包括用氧化钠或氧化钾处理式 VII 的 N-取代-4-硝基邻苯二甲酰亚胺，形成式 VIII 的 N-取代-4-苯氧基邻苯二甲酰亚胺，然后用例如锌，在碱存在下，得到式 I 的 5-苯氧基-1(3H)-异苯并呋喃酮、其异构体式 Ia 的 6-苯氧基-1(3H)-异苯并呋喃酮和烷基胺或芳基胺 NH2R（式 IX）