N-tert-butyl-(2-thienylmethylideneamine) N-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-tert-butyl-(2-thienylmethylideneamine) N-oxide
• 英文别名: (Z)-N-tert-butyl-1-(thiophen-2-yl)methanimine oxide；N-tert-butyl-1-thiophen-2-ylmethanimine oxide
• 化学式: C₉H₁₃NOS
• 分子量: 183.274
• InChiKey: SAOCTAYPIKITDD-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 N-叔丁基羟胺盐酸盐 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以85%的产率得到N-tert-butyl-(2-thienylmethylideneamine) N-oxide
  参考文献：
  名称：

  摘要：

  The spin-spin coupling constants (3)J(C,H) between the hydrogen atom of the aldonitrone group and the carbon atom bound to the nitrogen atom of the N-oxide fragment were determined for a wide range of cyclic and acyclic aldonitrones. Based on comparison of these constants (trans-(3)J(C,H) (E isomer) > cis-(3)J(C,H) (Z isomer)), the Z configuration was assigned to acyclic nitrones. Coordination of organolithium compounds to the oxygen atom of the N-->O group was revealed by C-13 NMR spectroscopy. This coordination is the necessary condition for the metallation of aldonitrones. The configuration of the nitrone group is responsible for the ability of the E form of acyclic aldonitrones to undergo CD3ONa-catalyzed isotope exchange of the methine proton in CD3OD and metallation with (BuLi)-Li-s.

  DOI：

  10.1023/a:1015459811377

文献信息

• NITRONE DERIVATIVES
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0945426A1

  公开（公告）日：1999-09-29

  A compound represented by the figure (1) or a pharmaceutically acceptable salt thereof is useful as a medicament for treating retinal degenerative disorders: wherein Ar is optionally substituted phenyl or optionally substituted heteroaryl;. n is 0, 1 or 2; W is -CH2NH- or -CH=N(O)-; R1, R2 and R3 are independently optionally substituted alkyl, carboxyl or alkoxycarbonyl; any two groups of R1, R2 and R3 may be taken together with the carbon atom to form optionally substituted cycloalkane; all of R1, R2 and R3 may be taken together with the adjusent carbon atom to form optionally substituted bicycloalkane or optionally substituted tricycloalkane; R4 and R5 are independently hydrogen atom or optionally substituted alkyl.

  图（1）所代表的化合物或其药学上可接受的盐可作为治疗视网膜变性疾病的药物： 其中 Ar 是任选取代的苯基或任选取代的杂芳基；. n 是 0、1 或 2； W是-CH2NH-或-CH=N(O)-； R1、R2 和 R3 独立地是任选取代的烷基、羧基或烷氧基羰基；R1、R2 和 R3 中的任意两个基团可与碳原子结合形成任选取代的环烷；所有 R1、R2 和 R3 可与相邻碳原子结合形成任选取代的双环烷或任选取代的三环烷； R4 和 R5 独立地为氢原子或任选取代的烷基。
• 10.1021/acs.joc.4c00512
  作者：Xing, Jian、Tang, Hong-Yu、Chen, Jing-Lin、Huang, Zheng、Liang, Jun-Jie、Quan, Yao-Sheng、Mao, Jian-Gang

  DOI：10.1021/acs.joc.4c00512

  日期：——

  methodology for the synthesis of nitrones via palladium-catalyzed redox cross-coupling of nitro compounds and alcohols is established. The protocol is a mild, convenient, ligand-free, and scalable synthesis method that can be compatible with various nitro compounds and alcohols. Nitrone is a significant multifunctional platform synthon which can be synthesized directly and efficiently via this tactic from

  建立了一种通过硝基化合物和醇的钯催化氧化还原交叉偶联合成硝酮的新方法。该方案是一种温和、方便、无配体、可扩展的合成方法，可以与各种硝基化合物和醇兼容。硝酮是一种重要的多功能平台合成子，可以通过这种策略从市售且廉价的原材料直接有效地合成。
• US6194461B1
  申请人：——

  公开号：US6194461B1

  公开（公告）日：2001-02-27
• ——
  作者：M. A. Voinov、I. A. Grigor"ev

  DOI：10.1023/a:1015459811377

  日期：——

  The spin-spin coupling constants (3)J(C,H) between the hydrogen atom of the aldonitrone group and the carbon atom bound to the nitrogen atom of the N-oxide fragment were determined for a wide range of cyclic and acyclic aldonitrones. Based on comparison of these constants (trans-(3)J(C,H) (E isomer) > cis-(3)J(C,H) (Z isomer)), the Z configuration was assigned to acyclic nitrones. Coordination of organolithium compounds to the oxygen atom of the N-->O group was revealed by C-13 NMR spectroscopy. This coordination is the necessary condition for the metallation of aldonitrones. The configuration of the nitrone group is responsible for the ability of the E form of acyclic aldonitrones to undergo CD3ONa-catalyzed isotope exchange of the methine proton in CD3OD and metallation with (BuLi)-Li-s.