N-iodomorpholine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-iodomorpholine
• 英文别名: 4-iodomorpholine
• 化学式: C₄H₈INO
• 分子量: 213.018
• InChiKey: YCQHTIDVLROXSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-iodomorpholine 、 Diphenylphosphine oxide 在 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以47%的产率得到morpholinodiphenylphosphine oxide
  参考文献：
  名称：

  通过N–H / P–H之间的氧化交叉偶联，有效地电合成次膦酰胺

  摘要：

  由二芳基膦氧化物和胺经电合成开发了一种简便有效的次膦酰胺方法。在温和和无金属的条件下，一步获得了多种次膦酰胺，并具有良好或优异的收率。研究了相应的机制。

  DOI：

  10.1039/c7gc01989k
• 作为产物：
  描述：

  吗啉 在 碘 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-iodomorpholine
  参考文献：
  名称：

  蓝藻丙酮酸脱氢酶复合物E1抑制剂的设计，合成和效价

  摘要：

  需要安全有效的除藻剂来控制具有农业和环境意义的藻类。四个系列（6，10，17，和21 29新的4-氨基嘧啶衍生物）的合理设计和合成。的一部分10，17，和21中显示的有效抑制大肠杆菌丙酮酸脱氢酶复合物E1（大肠杆菌PDHC-E1）（IC 50 = 2.12-18.06μM）和抑制良好的集胞藻属。PCC 6803（EC 50 = 0.7–7.1μM）和微囊藻。FACH 905（EC 50= 3.7–7.6μM）。这些化合物的杀藻活性与它们对大肠杆菌PDHc-E1的抑制作用正相关。特别是21l和10b表现出对PCC 6803的强效杀藻活性（分别为EC 50 = 0.7和0.8μM），其值是硫酸铜（EC 50 = 1.8μM）的2倍，并且表现最佳抑制蓝细菌PDHc-E1（IC 50分别为5.10和6.06μM ）。17h和21e是大肠杆菌的最佳抑制剂通过分子对接，定点诱变和酶促测定研究了PDHc

  DOI：

  10.1021/acs.biochem.7b00636
• 作为试剂：
  描述：

  1,3-二乙炔苯 在 N-iodomorpholine 、 copper(l) iodide 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 1,3-bis(5-iodo-1-((R)-1-phenylethyl)-1H-1,2,3-triazol-4-yl)benzene
  参考文献：
  名称：

  5-Iodo-1,2,3-triazolium-based multidentate halogen-bond donors as activating reagents

  摘要：

  基于5-碘-1,2,3-三唑鎓基团的双齿和三齿多阳离子卤素键供体已通过1,3-极性环加成反应合成。这些基于卤素的路易斯酸已在卤化物提取基准反应中作为催化剂进行了评估。

  DOI：

  10.1039/c2cc34392d

文献信息

• COPPER CATALYZED CYCLOADDITION OF ORGANIC AZIDES AND 1-HALOALKYNES
  申请人：Hein Jason E.

  公开号：US20120142935A1

  公开（公告）日：2012-06-07

  This invention provides a method for preparing a 1,2,3-triazole compound comprising contacting an organic azide with a 2-substituted-1-haloalkyne, in the presence of a copper catalyst and a copper-coordinating ligand (preferably a tertiary amine) in a liquid reaction medium, thereby forming a 1,4,5-substituted-1,2,3-triazole compound including a halo substituent at the 5-position of the triazole, the organic portion of the organic azide at the 1-position of the triazole, and the substituent of the 1-iodoalkyne at the 4-position of the triazole. A method for preparing 1-iodoalkynes is also provided.

  本发明提供了一种制备1,2,3-三唑化合物的方法，包括在液态反应介质中，在铜催化剂和铜配位配体（优选为三级胺）的存在下，将有机叠氮化合物与2-取代-1-卤代烯烃接触，从而形成1,4,5-取代的1,2,3-三唑化合物，包括三唑环的5-位上的卤代取代基，有机叠氮化合物的1-位上的有机部分，以及1-碘代烯烃的取代基在三唑环的4-位上。本发明还提供了制备1-碘代烯烃的方法。
• Copper catalyzed cycloaddition of organic azides and 1-haloalkynes
  申请人：Hein Jason E.

  公开号：US08927736B2

  公开（公告）日：2015-01-06

  This invention provides a method for preparing a 1,2,3-triazole compound comprising contacting an organic azide with a 2-substituted-1-haloalkyne, in the presence of a copper catalyst and a copper-coordinating ligand (preferably a tertiary amine) in a liquid reaction medium, thereby forming a 1,4,5-substituted-1,2,3-triazole compound including a halo substituent at the 5-position of the triazole, the organic portion of the organic azide at the 1-position of the triazole, and the substituent of the 1-iodoalkyne at the 4-position of the triazole. A method for preparing 1-iodoalkynes is also provided.

  本发明提供了一种制备1,2,3-三唑化合物的方法，包括在液体反应介质中，在铜催化剂和铜配位配体（优选为三级胺）的存在下，将有机偶氮化物与2-取代的1-卤代烷炔接触，从而形成1,4,5-取代的1,2,3-三唑化合物，其中三唑的5-位上含有卤素取代基，有机偶氮化物的有机部分在三唑的1-位上，1-碘代烷炔的取代基在三唑的4-位上。本发明还提供了一种制备1-碘代烷炔的方法。
• Synthesis of <i>ortho</i>-Haloaminoarenes by Aryne Insertion of Nitrogen–Halide Bonds
  作者：Charles E. Hendrick、Qiu Wang

  DOI：10.1021/jo502541t

  日期：2015.1.16

  A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of NX insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.
• Structure optimization and bioactivity evaluation of ThDP analogs targeting cyanobacterial pyruvate dehydrogenase E1
  作者：Jiangtao Feng、Haifeng He、Yuan Zhou、Meng Cai、Hao Peng、Honglin Liu、Lei Liu、Lingling Feng、Hongwu He

  DOI：10.1016/j.bmc.2019.115159

  日期：2019.12

  Harmful cyanobacteria bloom (HCB) has occurred frequently in recent years and it is urgent to develop novel algicides to deal with this problem. In this paper, a series of novel thiamin diphosphate (ThDP) analogs 5a-5g were designed and synthesized targeting cyanobacterial pyruvate dehydrogenase complex E1 (Cy-PDHc E1). Our results showed that compounds 5a-5g have higher inhibitory activities against Cy-PDHc E1 (IC50 9.56-3.48 mu M) and higher inhibitory activities against two model cyanobacteria strains Synechocystis sp PCC6803 (EC50 2.03-1.58 mu M) and Microcystis aeruginosa FACHB905 (EC50 1.86-0.95 mu M). Especially, compound 5b displayed highest inhibitory activities (IC50 = 3.48 mu M) against Cy-PDHc E1 and powerful inhibitory activities against cyanobacteria Synechocystis sp PCC6803 (EC50 = 1.58 mu M) and Microcystis aeruginosa FACHB905 (EC50 = 1.04 mu M). Moreover, the inhibitory activities of compound 5b were even higher than those of copper sulfate (EC50 = 2.02 and 1.71 mu M separately) which has been widely used as algicide against cyanobacteria PCC6803 and FACHB905. The more important was that compound 5b display much higher inhibitory selectivity between Cy-PDHc E1 (Inhibitory rate 97.4%) and porcine PDHc E1 (Inhibitory rate 11.8%) under the same concentration (100 mu M). The inhibition kinetic experiment and molecular docking research showed that compound 5b can inhibit Cy-PDHc E1 by occupying the ThDP-binding pocket and then blocking Cy-PDHc E1 bound to ThDP as competitive inhibitor. The imagines of SEM and TEM showed that cellular microstructures were heavily destroyed under compound 5b stress. Our results demonstrated compound 5b could be taken as a potential lead compound targeting Cy-PDHc E1 to obtain environment-friendly algicide for harmful cyanobacterial blooms control.
• Pyrazoles with a “click” 4-[N-(4-fluorobutyl)-1,2,3-triazole] substituent in position 3 are nanomolar CB1 receptor ligands
  作者：Rita Distinto、Chiara Zanato、Serena Montanari、Maria Grazia Cascio、Paolo Lazzari、Roger Pertwee、Matteo Zanda

  DOI：10.1016/j.jfluchem.2014.07.010

  日期：2014.11

  Replacement of the 3-carbonylaminopiperidine substitutent with a "click" 4-[N-(4-fluorobutyl)-(1,2,3-triazolyl)] group in Rimonabant-type pyrazoles produced a novel class of nanomolar CB1 receptor ligands. Molecule 1d is the most promising lead with a K-i=23 nM for CB1, which is very close to that displayed by Rimonabant (SR141716), and fairly good CB1/CB2 selectivity (K-i CB2/K-i CB1 = 35.5), thus representing a promising candidate for [F-18]radiolabeling and PET Imaging studies of the CB1 receptor. (C) 2014 Elsevier B.V. All rights reserved.