N-benzyl-α-(2-chlorophenyl)nitrone | 22687-07-6

• 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-benzyl-α-(2-chlorophenyl)nitrone
• 英文别名: N-benzyl-1-(2-chlorophenyl)methanimine oxide
• CAS: 22687-07-6
• 化学式: C₁₄H₁₂ClNO
• 分子量: 245.708
• InChiKey: HGLLFQYGKHVMKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-α-(2-chlorophenyl)nitrone 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 73.3h， 生成 2-benzyl-3-o-chloro-phenyl-isoxazolidine-5,5-diyl-bisphosphonic acid
  参考文献：
  名称：

  Efficient synthesis of isoxazolidine-substituted bisphosphonates by 1,3-dipolar cycloaddition reactions

  摘要：

  Several bisphosphonates bearing a substituted isoxazolidine ring have been synthesized in good yield by direct 1,3-dipolar cyclization reaction, under microwaves catalysis, in the absence of solvent. The method allows the simultaneous incorporation, on the geminal position of the bisphosphonate framework, of a basic nitrogen and of an oxygen atom, as third hook. Hydrophobicity-hydrophilicity of BPs is discussed with the help of distribution coefficients. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.098
• 作为产物：
  描述：

  氯化苄 在 水 、 碳酸氢钠 作用下， 生成 N-benzyl-α-(2-chlorophenyl)nitrone
  参考文献：
  名称：

  Neubauer, Justus Liebigs Annalen der Chemie, 1897, vol. 298, p. 193

  摘要：

  DOI：

文献信息

• Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes
  作者：Teppei Otsuki、Jun Kumagai、Yoshihito Kohari、Yuko Okuyama、Eunsang Kwon、Chigusa Seki、Koji Uwai、Yasuteru Mawatari、Nagao Kobayashi、Tatsuo Iwasa、Michio Tokiwa、Mitsuhiro Takeshita、Atushi Maeda、Akihiko Hashimoto、Kana Turuga、Hiroto Nakano

  DOI：10.1002/ejoc.201500926

  日期：2015.11

  The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical

  在对映选择性 1 中检查了简单氨基醇的催化活性，该基团包含一个庞大的超级甲硅烷基 [即，三（三甲基甲硅烷基）甲硅烷基（TTMSS）] 键合到 γ 位的氧原子以及伯胺部分，硝酮与 α,β-不饱和醛的 3-偶极环加成反应。该有机催化剂以良好的化学产率（高达 86%）成功地提供了具有优异非对映选择性（内/外，高达 96:4）和对映选择性（高达 97% ee）的光学活性异恶唑烷。此外，获得的异恶唑烷很容易转化为含有三个连续立体中心的 γ-氨基二醇。
• Efficient and mild Strecker-type reaction of nitrones catalyzed by MgI₂ etherate
  作者：Zhili Chen、Xinyu Zhou、Xiaoqiang Xie、Xingxian Zhang

  DOI：10.1080/00397911.2017.1350276

  日期：2017.10.2

  ABSTRACT An efficient Strecker-type reaction of nitrones with trimethylsilyl cyanide (TMSCN) catalyzed by MgI2 etherate has been achieved in a short time under mild condition. The condensations of aromatic nitrones, heterocyclic nitrones, and aliphatic nitrones with TMSCN are performed in good to excellent yields. Further dehydration of α-cyanohydroxylamine smoothly produced the α-imine nitrile in

  摘要 在 MgI2 醚合物催化下，硝酮与三甲基氰化甲硅烷 (TMSCN) 的高效 Strecker 型反应已在短时间内在温和条件下实现。芳族硝酮、杂环硝酮和脂肪族硝酮与 TMSCN 的缩合反应收率非常好。α-氰基羟胺的进一步脱水通过在甲醇中的 2.0 mol/L HCl 处理水解顺利地产生了 α-亚胺腈。图形概要
• Hybrid Diamines Derived from 1,1′-Binaphthyl-2,2′-diamine and α-Amino Acids as Organocatalysts for 1,3-Dipolar Cycloaddition of Aromatic Nitrones to (E)-Crotonaldehyde
  作者：Janusz Jurczak、Łukasz Weseliński、Paweł Stępniak

  DOI：10.1055/s-0029-1217808

  日期：2009.9

  2'-diamine and various α-amino acids were prepared using a convenient procedure. They were tested as organocatalysts for 1,3-dipolar cycloaddition of aromatic nitrones to (E)-crotonaldehyde. The L-pbenylalanine-based catalyst 10 afforded superior results, with good endo diastereoselectivity, and enantioselectivity of up to 95% ee.

  使用方便的程序制备 1,1'-联萘-2,2'-二胺和各种 α-氨基酸的同手性衍生物。将它们作为有机催化剂进行测试，用于芳族硝酮与 (E)-巴豆醛的 1,3-偶极环加成反应。L-苯丙氨酸基催化剂 10 提供了优异的结果，具有良好的内非对映选择性和高达 95% ee 的对映选择性。
• Modified N,O-Nucleosides: Design, Synthesis, and Anti-tumour Activity
  作者：Loredana Maiuolo、Olga Bortolini、Antonio De Nino、Beatrice Russo、Riccardo Gavioli、Fabio Sforza

  DOI：10.1071/ch13511

  日期：——

  A preliminary library of modified N,O-nucleosides was prepared and tested on a selected number of human cancer lines that include SKOV3, SW480, and K562. Thymine, N-benzyl substituents, and aromatic rings contribute to an increase of the biological activity, up to 10–25 μM, that appeared also reliant on the calculated lipophilicity of the nucleosides, expressed as cLogP, where P represents the partition

  制备了修饰的N，O-核苷的初步文库，并在包括SKOV3，SW480和K562在内的选定数量的人类癌症株系上进行了测试。胸腺嘧啶，N-苄基取代基和芳环有助于提高生物活性，最高可达10–25μM，这也取决于计算出的核苷亲脂性，表示为cLogP，其中P代表a的分配系数。在正辛醇和水之间溶解。
• Synthesis and antitumor activities of α-hydroxyamino phosphine oxides by catalyst-free hydrophosphinylation of nitrones
  作者：Pengfei Zhao、Peiyuan Li、Jian Xiao、Yali Wang、Xiaohui Hao、Aiguo Meng、Chunyan Liu

  DOI：10.1039/d2cc06981d

  日期：——

  Inspired by the diverse bioactivities of α-amino phosphine oxides, an efficient strategy for the synthesis of less researched α-(hydroxyamino)diarylphosphine oxides has been developed and their antitumor activities are explored. Under water as a solvent and catalyst-free conditions, the addition of nitrones and diphenylphosphine oxide occurs smoothly to afford α-(hydroxyamino) diarylphosphine oxides

  受 α-氨基氧化膦多种生物活性的启发，开发了一种合成较少研究的 α-（羟基氨基）二芳基氧化膦的有效策略，并探索了它们的抗肿瘤活性。在水作为溶剂和无催化剂条件下，硝酮和二苯基氧化膦的加成反应顺利进行，以高收率得到 α-(羟基氨基) 二芳基氧化膦。该反应具有底物适用范围广、原料易得、原子经济、纯化容易等特点。此外，生物学评估表明，两种合成衍生物5e和5f可以作为有趣的抗癌剂进一步开发。