2-(1,3-dioxoisoindolin-2-yl)benzoyl chloride | 90303-35-8

• 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: 2-(1,3-dioxoisoindolin-2-yl)benzoyl chloride
• 英文别名: 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzoyl chloride；2-phthalimido-benzoyl chloride；Phthalimidyl-benzoyl chloride；2-(1,3-dioxoisoindol-2-yl)benzoyl chloride
• CAS: 90303-35-8
• 化学式: C₁₅H₈ClNO₃
• 分子量: 285.686
• InChiKey: RUAPDRZGCVPCCV-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  462.8±47.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,3-dioxoisoindolin-2-yl)benzoyl chloride 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以60%的产率得到o-phthalimidobenzoic acid azide
  参考文献：
  名称：

  Fahmy, A. F. M.; Aly, N. F.; Mohamed, M. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 308 - 311

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯二甲酰氯 在 氯化亚砜 、 三乙胺 作用下， 生成 2-(1,3-dioxoisoindolin-2-yl)benzoyl chloride
  参考文献：
  名称：

  Self-Assembly of Zinc Porphyrins around the Periphery of Hydrogen-Bonded Aggregates That Bear Imidazole Groups

  摘要：

  This paper describes the preparation and characterization of four aggregates that are based an the rosette of derivatives of isocyanuric acid (CA) and melamine (M). These aggregates comprise a trismelamine, hub(M-Im)(3), that presents imidazole groups around its periphery; these imidazoles organize zinc tetraphenyl porphyrin (ZnTPP) by coordination of the imidazole to the zinc center. Aggregate 1 forms a single rosette upon mixing 1 equiv of hub(M-Im)(3) and 3 equiv of CA. Adding 3 equiv of ZnTPP yields 2. Aggregate 3 forms as a stacked bisrosette upon mixing 2 equiv of hub(M-Im)(3) and 3 equiv of bisCA. Adding 6 equiv of ZnTPP yields 4. The stoichiometries of aggregates 1-4 were obtained by titrating the trismelamines with CA and by titrating the aggregates with ZnTPP. The stoichiometry is defined as the ratio at which additional CA remains insoluble or additional ZnTPP appears as free ZnTPP in the H-1 NMR spectrum. Electrospray ionization mass spectrometry (ESI-MS) is compatible with the measured stoichiometries, The structures of these aggregates were determined using variable-temperature H-1 NMR spectroscopy;analogous structures were inferred for 5 and 6, the tert-butyl analogues of 1 and 2. The shapes of the traces from gel permeation chromatography (GPC) suggest that imidazole groups destabilize the aggregates when they are not involved in coordination to zinc; that is, the stability seems to be 6 approximate to 4 > 3 and 5 approximate to 2 > 1. A direct comparison of the relative stability of 1, 2, and 5 confirms the results of the GPC analysis: mixing 1 (hub(M-IM)(3).3CA) with the trismelamine component of 5 (hub(M)(3)) leads to the formation of a 3:2 mixture of 5:1. Adding ZnTPP to this solution leads to a 3:2 mixture of 5:2 with free trismelamines remaining in solution: 1 is not observed, The results of UV/vis spectroscopy are consistent with the other spectroscopic and chromatographic results and indicate that 3 equiv of ZnTPP are organized around the periphery of 2 and at least 4 equiv around the periphery of 4.

  DOI：

  10.1021/jo9615458

文献信息

• Furan ring opening–pyrrole ring closure: a new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines
  作者：Alexander V. Butin、Tatyana A. Nevolina、Vitaly A. Shcherbinin、Igor V. Trushkov、Dmitry A. Cheshkov、Gennady D. Krapivin

  DOI：10.1039/c002994g

  日期：——

  presence of alkyl or aryl groups on amide nitrogen due to competitive furfuryl cation elimination. But alkylation of pyrrolo[1,2-a][1,4]benzodiazepines yields efficiently the corresponding N-alkyl derivatives. Steric effects also prevent cyclization due to reversibility of diazepine ring formation under these reaction conditions. However, the corresponding pyrrolo[1,2-a][1,4]benzodiazepines can be obtained

  描述了吡咯并[1,2- a ] [1,4]苯并二氮杂s的合成方法。该方法是基于用Na 2 O 3处理的N-（糠基）蒽酰胺的再循环。盐酸/醋酸 系统，并允许两者同时形成 地西平和吡咯环一步就形成。反应通过 呋喃开环成二酮部分，随后NH 2-基团与两个羰基官能团连续相互作用。由于竞争性糠基阳离子消除，该方法在酰胺氮上存在烷基或芳基的情况下效率不高。但是吡咯并[1,2- a ] [1,4]苯并二氮杂卓的烷基化有效地产生了相应的N-烷基衍生物。在这些反应条件下，由于二氮杂ring环形成的可逆性，立体效应也阻止了环化作用。但是，相应的吡咯并[1,2- a ] [1,4]苯并二氮杂卓可通过逐步方法获得，即1）呋喃环开环为aq。盐酸/醋酸 和2）在冰河处理下，将分离的氨基二酮环化 醋酸。合成吡咯并[1,2- a ] [1,4]苯并二氮杂卓的另一种有效方法是酸催化N-（糠基）-2-硝基苯甲酰胺的呋喃环开环，然后处理所形成的吡咯并[1
• A novel approach to isoindolo[2,1-a]indol-6-ones
  作者：Philip Duncanson、Yuen-Ki Cheong、Majid Motevalli、D. Vaughan Griffiths

  DOI：10.1039/c2ob25314c

  日期：——

  A convenient route to isoindolo[2,1-a]indol-6-ones has been developed starting from the appropriate 2-(N-phthaloyl)benzoic acids. Formation of the acid chlorides with thionyl chloride followed by heating with triethyl phosphite in a suitable solvent resulted in a multistep reaction giving tetracyclic β-ketophosphonates that on reduction with sodium borohydride gave the required indolones in good overall

  从合适的2-（N-邻苯二甲酰基）苯甲酸开始，已经开发出一种方便的方法制备异吲哚并[2，1 - a ]吲哚-6-酮。形成酰氯与亚硫酰氯 然后用 亚磷酸三乙酯 在合适的溶剂中进行多步反应，得到四环β-酮膦酸酯，将其还原为 硼氢化钠以良好的总收率获得了所需的吲哚酮。还从N，N-（1,8-萘基）-2-氨基苯甲酸和2-（2,5-二氧代-2,5-二氢-1 H-吡咯-1-基）开始制备类似的β-酮膦酸酯苯甲酸，尽管其中只有萘基产物可被还原硼氢化钠 而不在环系统中裂解酰胺键。
• Design, synthesis and antiinflammatory activity of novel phthalimide derivatives, structurally related to thalidomide
  作者：Alexandre Légora Machado、Lı́dia Moreira Lima、João Xavier Araújo-Jr、Carlos Alberto M. Fraga、Vera Lúcia Gonçalves Koatz、Eliezer J. Barreiro

  DOI：10.1016/j.bmcl.2004.12.012

  日期：2005.2

  As part of an ongoing effort to develop new thalidomide analogues as antiinflammatory lead-candidates, this paper describes the synthesis and antiinflammatory activity of novel N-phenyl-phthalimide functionalized derivatives (4a-d, 5a,b, 6a,b). The target compounds were assayed in an acute lung inflammatory model and all compounds were able to inhibit TNF-alpha production and subsequent neutrophil

  作为开发新的沙利度胺类似物作为抗炎先导候选药物的持续努力的一部分，本文描述了新型N-苯基-邻苯二甲酰亚胺官能化衍生物（4a-d，5a，b，6a，b）的合成和抗炎活性。在急性肺炎模型中测定了目标化合物，并且所有化合物均能够在LPS急性肺炎模型中抑制TNF-α的产生和随后的中性粒细胞募集。
• Synthesis of Some New Heterocycles Derived from Novel 2-(1,3-Dioxisoindolin-2-yl)Benzoyl Isothiocyanate
  作者：Magdy M. Hemdan、Amira A. El-Sayed

  DOI：10.1002/jhet.2287

  日期：2016.3

  Novel 2‐(1,3‐Dioxisoindolin‐2‐yl)benzoyl isothiocyanate was prepared and underwent addition–cyclization reactions with some nucleophilic reagents. Simultaneous or subsequent cyclization of the obtained adducts gave a diverse range of differently sized heterocycles and thioureas. The structures of the synthesized compounds were confirmed by microanalytical and spectral data.

  制备了新颖的2-（1,3-二氧异吲哚-2-基）苯甲酰基异硫氰酸酯，并与某些亲核试剂进行了加成环化反应。同时或随后将获得的加合物环化，可得到各种不同尺寸的杂环和硫脲。通过微观分析和光谱数据证实了合成化合物的结构。
• INDICATOR FOR ASSESSING BODY ODOR, PROCESS FOR PRODUCING THE SAME, BODY ODOR ASSESSMENT METHOD, METHOD OF ASSESSING EFFICACIOUSNESS OF DEODORANT AND KIT FOR CONVENIENTLY ASSESING BODY ODOR
  申请人：Kao Corporation

  公开号：EP1553411A1

  公开（公告）日：2005-07-13

  An indicator material for assessing body odor of the present invention comprises at least one member selected from the group consisting of a substance (A) which is a β-hydroxycarboxylic acid compound represented by the formula (1), a substance (B) which is a derivative of the compound represented by the formula (1), a substance (C) which is an alcohol compound having a mercapto group at the 3-position represented by the formula (2),and a substance (D) which is a derivative of the compound represented by the formula (2). The present invention also provides a method of producing the compound represented by the formula (2) by incubating perspiration originated from a human in an environment with an oxygen concentration of 10 v/v% or less. The present invention also provides a kit for assessing body odor of a human, wherein the kit for assessing body odor of a human includes a coloration reagent which reacts with β-hydroxycarboxylic acid originated from perspiration of a human. wherein R1 is an alkyl having 1 to 4 carbons; R2 is a hydrogen atom or an alkyl having 1 to 4 carbons, and the total number of carbons in the formula (1) is 10 or less; wherein R3 is a hydrogen atom or methyl group; R4 is an alkyl group having 1 to 3 carbons; and R5 is a hydrogen atom or a methyl group, the total number of carbons is 8 or less.

  本发明的一种用于评估体味的指示剂材料包括至少一种选自以下组成的成员：一种物质（A），它是β-羟基羧酸化合物，由式（1）表示；一种物质（B），它是由式（1）表示的化合物的衍生物；一种物质（C），它是由式（2）表示的在3-位上具有巯基的醇化合物；以及一种物质（D），它是由式（2）表示的化合物的衍生物。本发明还提供了一种通过在氧气浓度为 10 v/v% 或更低的环境中培养人的汗液来生产式（2）所代表的化合物的方法。本发明还提供了一种用于评估人的体味的试剂盒，其中用于评估人的体味的试剂盒包括一种与源自人的汗液的β-羟基羧酸反应的着色试剂。 其中 R1 是具有 1 至 4 个碳原子的烷基；R2 是氢原子或具有 1 至 4 个碳原子的烷基，且式（1）中的碳原子总数为 10 或更少； 其中 R3 是氢原子或甲基；R4 是具有 1 至 3 个碳原子的烷基；R5 是氢原子或甲基，碳原子总数为 8 或更少。