Vilsmeier-Haack reagent

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: Vilsmeier-Haack reagent
• 英文别名: Vilsmeier reagent；Chloromethylidene(dimethyl)azanium;dichlorophosphinate
• 化学式: C₃H₇ClN*Cl₂O₂P
• 分子量: 226.427
• InChiKey: DWODIMJPOPDEIC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Vilsmeier-Haack reagent 以84%的产率得到
  参考文献：
  名称：

  YOSHIHARA MASAKUNI; EDA TSUNEHITO; SAKAKI KEISHI; MAESHIMA TOSHIHISA, SYNTHESIS, 1980, NO 9, 746-748

  摘要：

  DOI：
• 作为产物：
  描述：

  生成 Vilsmeier-Haack reagent
  参考文献：
  名称：

  PENSIONEROVA, G. A.;ROZINOV, V. G.;KALABINA, A. V.;DONSKIX, V. I.;RATOVSK+, ZH. OBSHCH. XIMII, 1982, 52, N 11, 2491-2499

  摘要：

  DOI：
• 作为试剂：
  描述：

  L-脯氨酰胺 在 Vilsmeier-Haack reagent 、 potassium carbonate 作用下， 以 醋酸异丙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.03h， 生成 维达列汀
  参考文献：
  名称：

  Synthesis of Vildagliptin Utilizing Continuous Flow and Batch Technologies

  摘要：

  The preparation and utilization of the Vilsmeier reagent (VR) is well-known in the literature with its usefulness and scope being frequently demonstrated in organic synthesis. However, it is an irritant and has a high thermal energy of decomposition; consequently, these factors lead to operational issues on larger scale which suggests approaches whereby the reagent is not isolated. Herein, we report the in-line formation and instantaneous consumption of VR utilizing both conventional batch and flow technologies. The approach is demonstrated by way of the synthesis of Vildagliptin, thereby mitigating potential safety and hygiene hazards

  DOI：

  10.1021/acs.oprd.5b00058

文献信息

• [EN] 2,3-SUBSTITUTED AZAINDOLE DERIVATIVES FOR TREATING VIRAL INFECTIONS<br/>[FR] DÉRIVÉS D'AZAINDOLES SUBSTITUÉS EN 2 ET 3 DESTINÉS AU TRAITEMENT D'INFECTIONS VIRALES
  申请人：SCHERING CORP

  公开号：WO2009032125A1

  公开（公告）日：2009-03-12

  The present invention relates to 2,3-Substituted Azaindole Derivatives, compositions comprising at least one 2,3-Substituted Azaindole Derivatives, and methods of using the 2,3-Substituted Azaindole Derivatives for treating or preventing a viral infection or a virus-related disorder in a patient.

  本发明涉及2,3-取代吡唑吲哚衍生物，包括至少一种2,3-取代吡唑吲哚衍生物的组合物，以及使用这些2,3-取代吡唑吲哚衍生物治疗或预防患者病毒感染或与病毒相关的疾病的方法。
• Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes
  作者：Roger W. Alder、Michael E. Blake、Simone Bufali、Craig P. Butts、A. Guy Orpen、Jan Schütz、Stuart J. Williams

  DOI：10.1039/b104110j

  日期：——

  Methods are described for the preparation of a range of N,N,N′,N′-tetraalkylformamidinium and N,N-dialkyliminium ions 4–20 as anhydrous salts for use as precursors to diamino- and amino-carbenes. These methods include a novel method involving nucleophilic addition to formamides followed by trapping with electrophiles such as triflic anhydride, various methods of formamide activation, exchange reactions involving orthoesters and the transamination of amidinium salts, and alkylation methods.

  本文描述了一系列N,N,N',N'-四烷基甲酰胺鎓和N,N-二烷基亚胺鎓离子4-20的制备方法，这些无水盐可用作二氨基和氨基碳烯的前体。这些方法包括一种新颖方法，涉及亲核加成到甲酰胺，随后用三氟甲磺酸酐等亲电试剂捕获，多种甲酰胺活化方法，涉及原酸酯的交换反应以及脒盐的转氨反应和烷基化方法。
• Synthèse régiospécifique d'amines tertiaires à groupe secondaire bi-insaturé
  作者：D. Mesnard、L. Miginiac

  DOI：10.1016/0022-328x(89)85018-1

  日期：1989.9

  We describe the regiospecific preparation of tertiary amines with a symmetrical (or dissymmetrical) doubly unsaturated secondary group, by reaction of an allylic, vinylic or acetylenic organometallic derivative with a dialkylformamido acetal, a chlorinated iminium salt or an alkynyl aminoether.

  我们描述了通过烯丙基，乙烯基或炔属有机金属衍生物与二烷基甲酰胺基缩醛，氯化亚胺盐或炔基氨基醚的反应，制备具有对称（或不对称）双不饱和仲基的叔胺的区域特异性制备方法。
• [EN] 1- OR 3-THIA-BENZONAPHTHOAZULENES AS INHIBITORS OF TUMOUR NECROSIS FACTOR PRODUCTION AND INTERMEDIATES FOR THE PREPARATION THEREOF<br/>[FR] 1- OU 3-THIA-BENZONAPHTHOAZULENES UTILISES COMME INHIBITEURS DE PRODUCTION DU FACTEUR DE NECROSE ET INTERMEDIAIRES DESTINES A LA PREPARATION DE CEUX-CI
  申请人：PLIVA D D

  公开号：WO2003084961A1

  公开（公告）日：2003-10-16

  The present invention relates to 1- or 3-thiabenzonaphthoazulene derivatives to their pharmacologically acceptable salts and solvates, to processes and intermediates for the preparation thereof as well as to their antiinflammatory effects, especially to the inhibition of tumour necrosis factor-alpha (TNF-alpha) production and the inhibition of interleukin-1 (IL-1) production as well as to their analgetic action.

  本发明涉及1-或3-硫代苯并萘蓝类衍生物及其药学上可接受的盐和溶剂化合物，以及其制备的过程和中间体，以及其抗炎作用，特别是对肿瘤坏死因子α（TNF-alpha）产生的抑制和白细胞介素-1（IL-1）产生的抑制，以及其镇痛作用。
• A new periodic mesoporous organosilica containing diimine-phloroglucinol, Pd(ii)-grafting and its excellent catalytic activity and trans-selectivity in C–C coupling reactions
  作者：Arindam Modak、John Mondal、Vinod K. Aswal、Asim Bhaumik

  DOI：10.1039/c0jm01180k

  日期：——

  A new organosilane precursor has been designed via Vilsmeier–Haack formylation of phloroglucinol followed by its Schiff base condensation with 3-aminopropyl-triethoxysilane (APTES). A novel organic–inorganic hybrid periodic mesoporous organosilica (PMO) LHMS-3 containing the highly coordinating bis(propyliminomethyl)-phloroglucinol moiety inside the pore wall has been synthesized by using this precursor organosilane molecule. Phenolic-OH and imine-N donor sites present in this PMO material have been utilized to anchor Pd(II) species at the surface of the mesopores. Small angle neutron scattering, XRD, HR TEM, SEM, 13C and 29Si solid state MAS NMR, UV-vis and FT IR spectroscopic tools are utilized to characterize the 2D-hexagonal mesophase and the presence of the bis(propyliminomethyl)-phloroglucinol moiety inside the pore wall. This Pd-anchored material Pd-LHMS-3 showed excellent catalytic activity and trans-selectivity in Heck C–C bond formation reactions for the synthesis of a series of value-added aromatic and aliphatic olefins.

  一种新的有机硅烷前驱体通过对酚羟基酸（phloroglucinol）进行Vilsmeier-Haack醛化反应，随后与3-氨基丙基三乙氧基硅烷（APTES）进行席夫碱缩合反应而设计合成。利用该有机硅烷前驱体合成了一种新型的有机-无机杂化周期性介孔有机硅材料（PMO）LHMS-3，含有高配位性的双（丙基亚氨基甲基）-酚羟基酸基团嵌入孔壁内。该PMO材料中的酚羟基-OH和亚胺-N供体位点被用来在介孔表面锚定Pd(II)物种。采用小角中子散射、X射线衍射、HR透射电子显微镜、扫描电子显微镜、13C和29Si固体核磁共振、紫外-可见光及傅里叶变换红外光谱等工具对该2D-六角介相及孔壁内的双（丙基亚氨基甲基）-酚羟基酸基团进行了表征。这种Pd锚定材料Pd-LHMS-3在Heck C-C键形成反应中表现出优异的催化活性和反式选择性，可用于合成一系列附加值的芳香族和脂肪族烯烃。