N-(2-hydroxyethyl)-4,5,6,7-tetrachlorophthalimide | 3891-09-6

• 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-(2-hydroxyethyl)-4,5,6,7-tetrachlorophthalimide
• 英文别名: N-(2-Hydroxyethyl)tetrachlorophthalimide；4,5,6,7-tetrachloro-2-(2-hydroxy-ethyl)-isoindoline-1,3-dione；4,5,6,7-Tetrachlor-2-(2-hydroxy-aethyl)-isoindolin-1,3-dion；4,5,6,7-Tetrachloro-2-(2-hydroxyethyl)isoindole-1,3-dione
• CAS: 3891-09-6
• 化学式: C₁₀H₅Cl₄NO₃
• 分子量: 328.967
• InChiKey: ZRPAQGZLVSNGGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-4,5,6,7-tetrachlorophthalimide 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 生成 (E)-1,2,3,4-Tetrachloro-5-phenyl-6,7,9,10-tetrahydro-8-oxa-10a-aza-cycloocta[a]inden-11-one
  参考文献：
  名称：

  Synthesis of medium and large ring heterocycles by photoinduced intermolecular and intramolecular electron transfer reactions of tetrachlorophthalimides with alkenes

  摘要：

  Photoinduced intermolecular and intramolecular electron transfer reactions of N-(omega -hydroxyalkyl)-tetrachlorophthalimide with alkenes led to the formation of medium to large sized heterocyclic rings. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01520-3
• 作为产物：
  描述：

  四氯苯二甲酸酐 生成 N-(2-hydroxyethyl)-4,5,6,7-tetrachlorophthalimide
  参考文献：
  名称：

  SALAXOV M. S.; GUSEJNOV M. M.; TREJVUS EH. M.; SALAXOVA R. S.; UMAEVA V. +, ZH. ORGAN. XIMII , 1976, 12, HO 8, 1719-1723

  摘要：

  DOI：

文献信息

• Photoinduced regioselective arylation of N-vinyllactams and methylthiazoles by tetrachlorophthalimides
  作者：Yong-Miao Shen、Guenter Grampp、Fei-Fei Tao、Ning-De He、Da-Qing Chen、Miao Ye

  DOI：10.1016/j.jphotochem.2013.07.017

  日期：2013.11

  Photoinduced reactions of 4,5,6,7-tetrahalophthalimides (1a–1h) with selected N-vinyllactams (N-vinylpyrrolidinone, N-vinylcaprolactam) and methylthiazoles respectively lead to dehydrohalogenative coupling reactions between the phthalimide and these heterocycles. These mild and metal-free coupling reactions result in regioselective and stereoselective arylation of the heterocycles by the phthalimide

  4,5,6,7-四卤代邻苯二甲酰亚胺（1a-1h）与选定的N-乙烯基内酰胺（N-乙烯基吡咯烷酮，N-乙烯基己内酰胺）和甲基噻唑的光诱导反应分别导致邻苯二甲酰亚胺与这些杂环之间的脱卤化氢偶合反应。这些温和且无金属的偶联反应导致邻苯二甲酰亚胺以Z-异构体为主要产物的杂环的区域选择性和立体选择性芳基化。讨论了光反应的反应机理
• Intermolecular Photocyclizations of N-(ω-Hydroxyalkyl)tetrachlorophthalimide with Alkenes Leading to Medium- and Large-Ring Heterocycles-Reaction Modes and Regio- and Stereoselectivity of the 1,n-Biradicals
  作者：Yong-Miao Shen、Xiao-Liang Yang、Da-Qing Chen、Jie Xue、Liang Zhu、Hoong-Kun Fun、Hong-Wen Hu、Jian-Hua Xu

  DOI：10.1002/chem.200902849

  日期：——

  A new photocyclization strategy by using intermolecular tandem reactions between N‐(ω‐hydroxyalkyl)‐4,5,6,7‐tetrachlorophthalimides (1, 2, and 3) and a series of acyclic and cyclic alkenes is reported. Electron transfer of the triplet‐excited phthalimide with the alkene and regioselective trapping of the alkene cation radical by the hydroxyl group at the phthalimide side chain gives a triplet 1,n‐biradical

  通过使用之间的分子间串联反应的新战略photocyclization Ñ（ω-羟烷基）-4,5,6,7- tetrachlorophthalimides（ - 1，2，和3被报告）和一系列无环和环状烯烃的。三重态激发的邻苯二甲酰亚胺与烯烃的电子转移，以及邻苯二甲酰亚胺侧链上的羟基对烯烃阳离子自由基的区域选择性捕集，得到三重态1，n-双自由基，在系统间交叉（ISC）之后导致具有含N，O的中环至大环的多环杂环的区域和非对映选择性合成。通过X射线衍射或广泛的2D NMR测量确定产物的明确空间结构，可以明确环化中的区域和非对映选择性。非对映选择性是由三重态1，n双自由基的ISC过程的立体化学过程决定的。这些分子间的光反应也提供了产生三重态1，n-双基的新策略。因此，在1和2与苯基环己烯的光反应中，在1中，分子内氢原子转移会前所未有地立体选择性地形成产物发现了正双基中间体（9和23）。这些事实直接验
• Allen; Nicholls, Journal of the American Chemical Society, 1934, vol. 56, p. 1410
  作者：Allen、Nicholls

  DOI：——

  日期：——
• [EN] AMINOHYDROCARBON PHOSPHONATE OLIGONUCLEOTIDES AND USES THEREFOR<br/>[FR] OLIGONUCLEOTIDES CONTENANT UNE FRACTION PHOSPHONATE D'AMINOHYDROCARBURE ET UTILISATION DESDITS OLIGONUCLEOTIDES
  申请人：PHARMGENICS, INC.

  公开号：WO1995031572A1

  公开（公告）日：1995-11-23

  (EN) A method for modulating the activity of a protein or nucleic acid $i(in vivo) by binding it with an oligonucleotide wherein at least one nucleotide unit includes an aminohydrocarbon phosphonate moiety having formula (I), wherein X is (II), and wherein R1 is a hydrocarbon, preferably alkylene, and R2, R3 and R4 are each independently hydrogen or a hydrocarbon. Preferably, R1 is methyl, ethyl or propyl moiety. It is also preferred to use the pure stereoisomers of such compounds rather than their racemic mixtures. Such pure stereoisomers having improved binding capabilities and improved resistance to nucleases. Alternatively, X may be (III), wherein R1, R2, and R3 are as hereinabove described, and R5 is a detectable marker, thus making such oligonucleotides useful as diagnostic probes or for screening libraries of cells.(FR) Procédé de modulation de l'activité d'une protéine ou d'un acide nucléique $i(in) $i(vivo) consistant à lier ladite protéine ou ledit acide nucléique avec un oligonucléotide, dans lequel au moins une unité oligonucléotidique comprend une fraction phosphonate d'aminohydrocarbure de formule (I) dans laquelle X est (II), dans laquelle R1 est un hydrocarbure, de préférence alkylène, et R2, R3 et R4 sont chacun indépendamment hydrogène ou un hydrocarbure. De préférence R1 est une fraction méthyle, éthyle ou propyle. Il est également préférable d'utiliser les stéréoisomères purs desdits composés plutôt que leurs mélanges racémiques, lesdits stéréoisomères purs ayant des capacités de liaison améliorées et une résistance améliorée aux nucléases. Alternativement, X peut être (III), dans laquelle R1, R2 et R3 sont tels que décrits ci-dessus, et R5 est un marqueur détectable, ce qui rend lesdits nucléotides utiles en tant que sondes diagnostiques et pour cribler des bibliothèques de cellules.
• Synthesis of medium and large ring heterocycles by photoinduced intermolecular and intramolecular electron transfer reactions of tetrachlorophthalimides with alkenes
  作者：Jie Xue、Liang Zhu、Hoong-Kun Fun、Jian-Hua Xu

  DOI：10.1016/s0040-4039(00)01520-3

  日期：2000.10

  Photoinduced intermolecular and intramolecular electron transfer reactions of N-(omega -hydroxyalkyl)-tetrachlorophthalimide with alkenes led to the formation of medium to large sized heterocyclic rings. (C) 2000 Elsevier Science Ltd. All rights reserved.