3-(benzyloxy)benzaldehyde oxime | 93033-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(benzyloxy)benzaldehyde oxime
• 英文别名: (NZ)-N-[(3-phenylmethoxyphenyl)methylidene]hydroxylamine；N-[(3-phenylmethoxyphenyl)methylidene]hydroxylamine
• CAS: 93033-58-0
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: YUQATBOXIFGNQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  3-(benzyloxy)benzaldehyde oxime 在 苯酐 作用下， 反应 0.08h， 以88%的产率得到3-(苄氧基)苯甲腈
  参考文献：
  名称：

  邻苯二甲酸酐脱水醛肟制备腈的有效方法

  摘要：

  建立了一种新的高效醛肟转化为腈的方法。通过与邻苯二甲酸酐的融合，醛肟以高产率（超过 85%）和在短时间内（5 分钟内）高效且顺利地转化为腈类。邻苯二甲酸酐、环状酸酐和融合态醛肟的混合物为酰化醛肟选择性[3.3]-σ迁移重排为腈建立了理想的过渡态。

  DOI：

  10.1002/jccs.200400093
• 作为产物：
  描述：

  3-苄氧基苯甲醛 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-(benzyloxy)benzaldehyde oxime
  参考文献：
  名称：

  二苯并氮杂连接的异恶唑：新型有效的α-葡萄糖苷酶抑制剂

  摘要：

  α-葡萄糖苷酶抑制是控制糖尿病高血糖的有效方法。在目前的研究中，根据他们作为抗糖尿病药物的文献，设计了作为异恶唑和二苯并氮杂支架混合体的新分子。为此，使用氧化腈-炔环加成 (NOAC) 反应制备了一系列二苯并氮杂连接的异恶唑 ( 33-54 )，并评估了它们的α-葡萄糖苷酶抑制活性，以探索治疗糖尿病的新方法。大多数化合物显示出对强效的抑制效力α葡糖苷酶（EC 3.2.1.20）的酶（IC 50 = 35.62±1.48至333.30±1.67 μ M）使用阿卡波糖作为参考药物（IC 50= 875.75 ± 2.08 µ M)。还确定了活性异恶唑的构效关系、动力学和分子对接研究，以研究酶-抑制剂相互作用。化合物33，40，41，46，48-50，和54显示结合与关键的氨基酸残基相互作用α葡糖苷酶的酶，如Lys156，Ser157，Asp242和Gln353。

  DOI：

  10.1016/j.bmcl.2021.127979

文献信息

• Regioselective reductions of various 3-aminosuccinimides; application to the synthesis of two heterocyclic systems
  作者：Jean-François Brière、Patricia Charpentier、Georges Dupas、Guy Quéguiner、Jean Bourguignon

  DOI：10.1016/s0040-4020(96)01157-x

  日期：1997.2

  The synthesis of novel pyrrolo[3,2-c]isoquinolines is investigated starting from 3-aminosuccinimides. Various known routes leading to 3-aminosuccinimides were tested but a new approach via nucleophilic addition of arylalkylamines on maleimide gave better results. The regioselectivity of the reduction of these compounds was shown to depend on the degree of substitution of the concerned 3-aminosuccinimide

  从3-氨基琥珀酰亚胺开始研究新型吡咯并[3,2-c]异喹啉的合成。测试了导致3-氨基琥珀酰亚胺的各种已知途径，但是通过在马来酰亚胺上亲核加成芳基烷基胺的新方法给出了更好的结果。这些化合物还原的区域选择性显示出取决于所关注的3-氨基琥珀酰亚胺的取代度。羟基内酰胺在原位形成，然后转化为乙氧基内酰胺。后者在生成亚胺盐后，提供了目标吡咯并异喹啉和另一种新的杂环系统的另外两种衍生物：3,6-甲基-2,5-苯并重氮化合物。
• Cyclic Hydroxamic Acid Analogues of Bacterial Siderophores as Iron-Complexing Agents prepared through the Castagnoli-Cushman Reaction of Unprotected Oximes
  作者：Olga Bakulina、Anton Bannykh、Dmitry Dar'in、Mikhail Krasavin

  DOI：10.1002/chem.201704389

  日期：2017.12.14

  The first application of multicomponent chemistry (the Castagnoli–Cushman reaction) toward the convenient one‐step preparation of cyclic hydroxamic acids is described. Cyclic hydroxamic acids are close analogues of bacterial siderophores (iron‐binding compounds) and form stable complexes with Fe3+ ions as confirmed by spectrophotometric measurements. These compounds are potential components for the

  描述了多组分化学（卡斯塔尼奥利-库什曼反应）在一步一步制备环状异羟肟酸中的首次应用。环状异羟肟酸是细菌铁载体（铁结合化合物）的紧密类似物，并通过分光光度法测量证实与Fe 3+离子形成稳定的络合物。这些化合物是设计用于铁超负荷疾病治疗的螯合剂以及基于铁载体的载体系统的潜在成分，这些载体系统可用于跨细菌细胞壁的抗生素递送。
• Design, Synthesis, and Biological Evaluation of a Novel Series of 4-Guanidinobenzoate Derivatives as Enteropeptidase Inhibitors with Low Systemic Exposure for the Treatment of Obesity
  作者：Zenichi Ikeda、Keiko Kakegawa、Fumiaki Kikuchi、Sachiko Itono、Hideyuki Oki、Hiroaki Yashiro、Hideyuki Hiyoshi、Kazue Tsuchimori、Kenichi Hamagami、Masanori Watanabe、Masako Sasaki、Youko Ishihara、Kimio Tohyama、Tomoyuki Kitazaki、Tsuyoshi Maekawa、Minoru Sasaki

  DOI：10.1021/acs.jmedchem.2c00463

  日期：2022.6.23

  pharmacological effects. Further optimization focusing on the in vitro IC50 value and T1/2, an indicator of dissociation time, followed by enhanced in vivo pharmacological activity based on the ester stability of the compounds, revealed two series of potent enteropeptidase inhibitors, a dihydrobenzofuran analogue ((S)-5b, SCO-792) and phenylisoxazoline (6b), which exhibited potent anti-obesity effects despite

  为了发现一系列新的肠肽酶强效抑制剂，一种定位于十二指肠刷状缘的膜结合丝氨酸蛋白酶，以最小的全身暴露评估了 4-胍基苯甲酸酯衍生物。1c对接模型能够安装额外的羧酸部分以获得与肠肽酶的额外相互作用，从而产生2a。在饮食诱导的肥胖 (DIO) 小鼠中，口服2a显着提高了粪便蛋白输出（一种药效学标志物），而皮下给药并未改变该参数。因此，2a的药理作用不需要全身暴露。进一步优化体外IC 50值和T 1/2，解离时间的指标，然后基于化合物的酯稳定性增强的体内药理活性，揭示了两个系列的强效肠肽酶抑制剂，二氢苯并呋喃类似物 ( ( S )-5b， SCO-792 ) 和苯基异恶唑啉 ( 6b )，尽管它们在 DIO 大鼠口服给药后全身暴露量较低，但仍表现出有效的抗肥胖作用。
• Efficient synthesis and utilization of phenyl-substituted heteroaromatic carboxylic acids as aryl diketo acid isosteres in the design of novel HIV-1 integrase inhibitors
  作者：Li-Fan Zeng、Hu-Shan Zhang、Yun-Hua Wang、Tino Sanchez、Yong-Tang Zheng、Nouri Neamati、Ya-Qiu Long

  DOI：10.1016/j.bmcl.2008.07.047

  日期：2008.8

  Three new types of aryl diketo acid (ADK) isosteres were designed by conversion of the biologically labile 1,3-diketo unit into heteroaromatic motif such as isoxazole, isothiazole, or 1H-pyrazole to improve the physicochemical property of ADK-based HIV-1 integrase (IN) inhibitors. The synthesis of the heteroaromatic carboxylic acids was established by employing phenyl beta-diketoester or benzaldehyde as the starting material and 1,3-dipolar cycloaddition as the key reaction. Of the compounds tested, the 3-benzyloxyphenyl-substituted isoxazole carboxylic acid displayed the best IN inhibitory and antiviral activities, with N-hydroxylamidation enhancing the in vitro and in vivo potency. These findings are important for further optimization of ADK-based IN inhibitors. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and anticancer activity of benzyloxybenzaldehyde derivatives against HL-60 cells
  作者：Chin-Fen Lin、Jai-Sing Yang、Chiung-Yun Chang、Sheng-Chu Kuo、Miau-Rong Lee、Li-Jiau Huang

  DOI：10.1016/j.bmc.2004.12.026

  日期：2005.3.1

  A series of benzyloxybenzaldehyde derivatives were prepared and tested against the HL-60 cell line for anticancer activity. Preliminary structure-activity relationships were established. It was discovered that 2-(benzyloxy)benzaldehyde (17), 2-(benzyloxy)-4-methoxybenzaldehyde (26), 2-(benzyloxy)-5-methoxybenzaldehyde (27), 2-(benzyloxy)-5-chlorobenzaldehyde (28), 2-[(3-methoxybenzyl)oxy]benzaldehyde (29), 2-[(2-chlorobenzyl)oxy]benzaldehyde (30), and 2-[(4-chlorobenzyl)oxy]benzaldehyde (31) exhibited significant activity at 1-10 muM. Among them, compound 29 was the most potent one. The morphological assessment and DNA fragmentation analysis indicated that these compounds arrested cell cycle progression at G2/M phase and induced cell apoptosis. They resulted in the loss of mitochondrial membrane potential after 12 h of treatment. (C) 2004 Elsevier Ltd. All rights reserved.