N-(4-trifluoromethylphenyl)-benzimidoyl chloride | 80819-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-trifluoromethylphenyl)-benzimidoyl chloride
• 英文别名: N-[4-(trifluoromethyl)phenyl]benzenecarboximidoyl chloride
• CAS: 80819-62-1
• 化学式: C₁₄H₉ClF₃N
• 分子量: 283.68
• InChiKey: RUZJVPRASYDISM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-trifluoromethylphenyl)-benzimidoyl chloride 在 碘苯二乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.17h， 生成 2,4-diphenyl-6-(trifluoromethyl)quinazoline
  参考文献：
  名称：

  Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines

  摘要：

  A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp(3))-C(sp(2)) and C(sp(2))-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp(3)C-H/sp(2)C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.

  DOI：

  10.1021/ol500864r
• 作为产物：
  描述：

  N-[4-(三氟甲基)苯基]苯甲酰胺 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 N-(4-trifluoromethylphenyl)-benzimidoyl chloride
  参考文献：
  名称：

  N-芳基苯甲腈离子。苯环中取代基的光化学生成及其对水中寿命和与叠氮化物离子的反应性的影响

  摘要：

  硝酸根离子Ar–C N + –Ar'已通过激光闪光光解 在含有20％的水溶液中 乙腈。这阳离子 是通过苯甲酰亚胺盐的光热解产生的 酯类Ar–CZ N–Ar'（Z = –OC 6 H 4 -4-CN），其中4-氰基苯氧化物为光化学离去基团。反应速率常数水测定（k w），叠氮化物离子（ka z）和氢氧化物（k OH）。这阳离子Ph–C N + –Ph居住的时间仅短50倍水相较于Ph–C N + –iPr（2）；因此，用N-苯基取代N-烷基的作用不大。这两个阳离子还显示了与亚硝基类似物相似的寿命，例如Ph–CH N +（Me）–Ph。因此，除了水与sp和sp 2相似的杂合系统的发生率相似，并且增加进入腈的空间最多只起到适度的作用。对于Ar'中的取代基随Ar等于而变化的系列苯基，log k w的哈米特图与σ相关，其中ρ = −1.4。对于Ar变化的系列，数据与σ +的相关性更好，尽管ρ +仅为-0

  DOI：

  10.1039/b107028m

文献信息

• Naphthyridone derivatives
  申请人：USV Pharmaceutical Corporation

  公开号：US04304914A1

  公开（公告）日：1981-12-08

  Compounds of the formula ##STR1## wherein each of R, R.sub.1 and R.sub.2 is independently H, alkyl, alkenyl, alkoxy, halo, hydroxy, trifluoromethyl, amino, alkylamino, cyano and nitro; R.sub.3 is carbalkoxy, carboxamide alkanoyl, trifluoromethyl and cyano; and Ar is heteroaryl or ##STR2## wherein R.sub.4 and R.sub.5 have the same meaning as each of R, R.sub.1 and R.sub.2 ; and acid addition salts thereof have cardiotonic and hypertensive activity.

  式（I）的化合物，其中R、R.sub.1和R.sub.2各自独立地为H、烷基、烯基、烷氧基、卤素、羟基、三氟甲基、氨基、烷基氨基、氰基和硝基；R.sub.3为羧酰烷氧基、酰胺基烷酰基、三氟甲基和氰基；Ar为杂芳基或式（II）其中R.sub.4和R.sub.5与R、R.sub.1和R.sub.2的含义相同；以及它们的酸盐具有心脏强心和高血压活性。
• BF₃-Promoted Ring Expansion of Iminylphosphiranes and Acylphosphiranes for Divergent Access to 1,2-Azaphospholidines and 1,2-Dihydrophosphetes
  作者：Mingyue Cui、Yang Xu、Rongqiang Tian、Zheng Duan

  DOI：10.1021/acs.orglett.3c04347

  日期：2024.3.8

  Ring expansion of strained small rings provides an efficient method for the synthesis of various high-value carbocycles and heterocycles. Here we report BF3·Et2O as both an activating reagent and fluorine source, enabling ring expansion of phosphirane and P–F bond formation. Treatment of 1-iminylphosphirane complexes with BF3·Et2O resulted in 1,2-azaphospholidines, while the reaction of 1-acylphosphirane

  应变小环的扩环为合成各种高价值碳环和杂环提供了一种有效的方法。在这里，我们报告BF 3 ·Et 2 O既作为活化剂又作为氟源，使得磷杂环扩环并形成P-F键。用BF 3 ·Et 2 O处理1-亚氨基正膦配合物得到1,2-氮杂磷烷，而1-酰基正膦配合物与BF 3 ·Et 2 O反应得到1,2-二氢磷酸酯。通过 N 和 O 原子对中间体鏻阳离子的亲核性来调整反应路径。
• Asymmetric aza-Claisen rearrangement of allyl imidates catalyzed by homochiral cationic palladium(II) complexes
  作者：Yasuhiro Uozumi、Kazuhiko Kato、Tamio Hayashi

  DOI：10.1016/s0957-4166(98)00059-7

  日期：1998.3

  The asymmetric aza-Claisen rearrangement of (E)-3-alkyl-2-propenyl N-[4-trifluoromethyl)phenyl]benzimidates was catalyzed by a homochiral cationic palladium(II) complex generated from PdCl2(S)-2-(2-diphenylphosphino)phenyl-4-benzyloxazoline} and silver tetrafluoroborate (Pd:silver=1:1) to give (S)-N-(1-alkyl-2-propenyl)-N-[4-(trifluoromethyl)phenyl]benzamide of up to 81% ee. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• First Enantioselective Catalyst for the Rearrangement of Allylic Imidates to Allylic Amides
  作者：Michael Calter、T. Keith Hollis、Larry E. Overman、Joseph Ziller、G. Greg Zipp

  DOI：10.1021/jo962090p

  日期：1997.3.1

  A series of Pd(II) complexes containing chiral diamine ligands were investigated as asymmetric catalysts for the rearrangement of allylic imidates to allyl amides. The best catalysts were cations obtained by dechlorination of dichloro[(S)-2-(isoindolinylmethyl)-N-methylpyrrolidine]palladium-(II) (II) (17) with silver salts in CH2Cl2. Catalyst 18 was studied thoroughly and shown by H-1 NMR and X-ray crystallography analysis to be a C-1 symmetric dimer (Figure 1). A series of related catalysts 22-27 having various counterions and anionic ligands were also prepared and studied as asymmetric catalysts for the rearrangement of allylic N-(4-trifluorophenyl)benzimidate 29 to allylic benzamide 30 (eq 4). Rearrangement of 29 in CH2Cl2 (48 h at 40 degrees C) in the presence of 5 mol % of 18 affords (-)-30 in 69% yield and 55% ee. Enantioselection is increased to 60% when an isomerically pure sample of 18 is employed. Chemical correlation of allylic benzamide 30 with (R)-norvaline established that (-)-30 has the R absolute configuration (Scheme 3). A cyclization-induced rearrangement mechanism (Scheme 1) requires that in the major pathway the imidate nitrogen attacks the re face of the olefin with Pd coordinated to the si face. These studies constitute the first report of asymmetric catalysis of the rearrangement of allylic imidates to allylic amides. However, significant hurdles remain to be overcome before the enantioselective rearrangement of allylic imidates becomes a practical route to enantioenriched nitrogen compounds.