(Z)-N-hydroxy-2-naphthimidoyl chloride | 854602-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-N-hydroxy-2-naphthimidoyl chloride
• 英文别名: (2Z)-N-hydroxynaphthalene-2-carboximidoyl chloride
• CAS: 854602-87-2
• 化学式: C₁₁H₈ClNO
• 分子量: 205.644
• InChiKey: YEEMQNSRCRZGRQ-QBFSEMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-hydroxy-2-naphthimidoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3,4-di-(2-naphthyl)furoxan
  参考文献：
  名称：

  设计为新型杀菌剂的呋喃喃衍生物的合成及抗真菌活性。

  摘要：

  设计并合成了呋喃喃衍生物3-11作为潜在的杀菌剂。通过原位由N-羟基亚氨酰氯2生成的相应的腈氧化物的二聚作用，制备对称取代的呋喃喃衍生物3a-j。关键中间体醛4的进一步官能团修饰生成了呋喃喃衍生物5-11。在250 ppm的广谱植物真菌中观察到了呋喃喃衍生物3-11的杀真菌活性。

  DOI：

  10.1271/bbb.62.1693
• 作为产物：
  描述：

  2-(nitromethyl)naphthalene 在 sodium methylate 、 四氯化钛 作用下， 生成 (Z)-N-hydroxy-2-naphthimidoyl chloride
  参考文献：
  名称：

  新型一锅法将伯硝基烷烃转化为羟肟基氯

  摘要：

  用碱处理伯硝基烷烃，然后与TiCl 4反应，得到高产率的羟肟基氯。

  DOI：

  10.1016/0040-4039(96)01359-7

文献信息

• Synthesis and binding properties of chiral macrocyclic barbiturate receptors: application to nitrile oxide cyclizations
  作者：Brian S. Rasmussen、Unai Elezcano、Troels Skrydstrup

  DOI：10.1039/b110865b

  日期：2002.7.11

  A series of chiral macrocyclic receptors containing a barbiturate binding domain based on two 2,6-diaminopyridine groups has been synthesized with the purpose of exploiting these for asymmetric 1,3-dipolar cycloadditions. Each macrocyclic host was built possessing an (R)-BINOL or a modified deoxycholate moiety as the chiral unit connected to the barbiturate binding domain with varying lengths of spacer. All the hosts with the exception of one were found to effectively bind a barbiturate–cinnamic acid conjugate with association constants in the order of 104 M−1 in CDCl3. The 1,3-dipolar cycloaddition between several arylnitrile oxides and the cinnamate conjugates were examined in the presence of stoichiometric amounts of a chiral receptor affording two regioisomeric isoxazolines. Enantiomeric excesses of up to 30% were obtained in one case for the major regioisomer. In most cases, the enantiomeric excesses could be measured directly from the crude 1H-NMR spectra owing to the diastereomeric interaction between the isoxazoline cycloadduct and the chiral receptor. The relatively low enantiofacial selectivities at the CC double bond of the cinnamate were attributed to the non-planar orientation of the barbiturate–cinnamate conjugate with respect to the receptor, as previously noted for the binding of barbital to an achiral macrocyclic host (S.-K., Chang, E. Fan, D. Van Engen and A. D. Hamilton, J. Am. Chem. Soc., 1991, 113, 7640), directing the cinnamate unit away from the chiral unit.

  一系列基于两个2,6-二氨基吡啶基团的巴比妥酸盐结合域的手性大环受体已被合成，旨在利用它们进行不对称的1,3-偶极环加成反应。每个大环主体构建时含有一个(R)-BINOL或修饰的脱氧胆酸部分作为手性单元，通过不同长度的间隔基与巴比妥酸盐结合域相连。除一种外，所有受体均能有效结合巴比妥酸盐-肉桂酸共轭物，其在CDCl3中的结合常数为10^4 M^-1数量级。在手性受体的定量存在下，考察了几种芳基腈氧化物与肉桂酸共轭物之间的1,3-偶极环加成反应，生成两种区域异构的异恶唑啉。在某例中，主要区域异构体的对映体过量达到30%。在多数情况下，由于异恶唑啉环加合物与手性受体之间的非对映异构相互作用，对映体过量可以直接从粗1H-NMR谱图中测得。肉桂酸在CC双键处的相对较低的对映选择性归因于巴比妥酸盐-肉桂酸共轭物相对于受体的非平面取向，这一点与以前报道的巴比妥酸盐与非手性大环受体的结合情况相似（Chang等，1991），导致肉桂酸部分远离手性单元。
• Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides
  作者：Ting Pan、Xing Gao、Sen Yang、Lan Wang、Yimin Hu、Min Liu、Wei Wang、Yongjun Wu、Bing Zheng、Hongchao Guo

  DOI：10.1021/acs.orglett.1c01921

  日期：2021.8.6

  In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed

  在本文中，我们设计并合成了一种新型环状碳酸酯，烯丙基碳酸亚乙酯（AECs）。以 AECs 作为反应性前体，我们开发了钯催化的 (3+3) AECs 与腈氧化物的环化。在温和的反应条件下，各种 AEC 在该反应中效果良好。可以以高产率 (≤ 98%) 以简便的方式获得各种具有烯丙基季立构中心的 5,6-二氢-1,4,2-二恶嗪衍生物。
• Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides
  作者：Takahiro Soeta、Suguru Takashita、Yoko Sakata、Yutaka Ukaji

  DOI：10.1039/c5ob02032h

  日期：——

  The reaction of (Z)-hydroximoyl chlorides with isocyanides promoted by phosphinic acid in the presence of triethylamine proceeds smoothly to afford α-(hydroxyimino)amides in good to high yields. Phosphinic acid plays an important role in effectively promoting the reaction. A wide range of (Z)-hydroximoyl chlorides and isocyanides were found to be suitable for this reaction.

  在三乙胺的存在下，（Z）-羟肟基氯与次膦酸促进的异氰酸酯的反应顺利进行，从而以高至高收率获得了α-（羟基亚氨基）酰胺。膦酸在有效促进反应中起重要作用。发现各种各样的（Z）-羟肟基氯和异氰酸酯适合于该反应。
• Leaving Group Assisted Strategy for Photoinduced Fluoroalkylations Using <i>N</i> -Hydroxybenzimidoyl Chloride Esters
  作者：Weigang Zhang、Zhenlei Zou、Yuanheng Wang、Yi Wang、Yong Liang、Zhengguang Wu、Youxuan Zheng、Yi Pan

  DOI：10.1002/anie.201812192

  日期：2019.1.8

  (RAEs) as alkyl radical precursors have been extensively developed for C−C bond formations. However, the analogous transformations of fluoroalkyl radicals from the corresponding acid or ester precursors remain challenging because of the high oxidation potential of the fluoroalkyl carboxylate anions. The newly developed N‐hydroxybenzimidoylchloride (NHBC) ester provides a general leaving group assisted

  作为烷基自由基前体的氧化还原活性酯（RAE）已广泛开发用于C-C键的形成。然而，由于氟代烷基羧酸根阴离子的高氧化潜力，从相应的酸或酯前体的氟代烷基自由基的类似转化仍然具有挑战性。新开发的N-羟基苯甲酰亚胺基氯（NHBC）酯提供了一般的离去基团辅助策略来生成氟烷基自由基组合，并且可以成功地用于光诱导的脱羧氢氟烷基化反应和未活化烯烃的杂芳基化反应。此外，DFT计算表明，NHBC酯是通过碳氟自由基途径进行的，而其他众所周知的RAE则是通过氮自由基途径进行的。
• Pd-Catalysed [3 + 2]-cycloaddition towards the generation of bioactive bis-heterocycles/identification of COX-2 inhibitors <i>via in silico</i> analysis
  作者：Elagandhula Sathish、Arshad J. Ansari、Gaurav Joshi、Akansha Pandit、Monika Shukla、Neha Kumari、Ashoke Sharon、Ved Prakash Verma、Devesh M. Sawant

  DOI：10.1039/d2ob00467d

  日期：——

  dihydroisoxazole ring by [3 + 2] cycloaddition of VECs (vinyl ethylene carbonates) and nitrile oxides, assisted by a Pd catalyst. Herein we explored hydroximoyl chlorides as versatile precursors for the in situ generation of nitrile oxides that were exploited to achieve the cycloaddition reaction on a vinyl group of VECs to generate bis-heterocycles. In silico-based studies of bis-heterocycles on the cyclooxygenase

  在目前的研究中，我们设想在 Pd 催化剂的辅助下，通过 VEC（碳酸乙烯亚乙酯）和氧化腈的 [3 + 2] 环加成反应合成含有二氢异恶唑环的双杂环。在这里，我们探索了羟肟酰氯作为原位生成腈氧化物的多功能前体，这些前体被用来在 VEC 的乙烯基上实现环加成反应以生成双杂环。双杂环化合物对环氧合酶 (COX) 酶的计算机模拟研究显示选择性 COX-2 抑制。