4-Ethynyl-4-hydroxy-2,2,6,6-tetramethylpiperidine | 53654-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-Ethynyl-4-hydroxy-2,2,6,6-tetramethylpiperidine
• 英文别名: 4-ethynyl-4-hydroxy-2,2,6,6-tetramethylpiperine；4-ethynyl-2,2,6,6-tetramethyl-piperidin-4-ol；4-Aethinyl-2,2,6,6-tetramethyl-piperidin-4-ol；4-Hydroxy-2,2,6,6-tetramethyl-4-aethinyl-piperidin；4-Hydroxy-2,2,6,6-tetramethyl-4-ethinyl-piperidin；4-Ethynyl-2,2,6,6-tetramethylpiperidin-4-ol
• CAS: 53654-26-5
• 化学式: C₁₁H₁₉NO
• mdl: MFCD00470315
• 分子量: 181.278
• InChiKey: WKHGZAFSCCRZQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Ethynyl-4-hydroxy-2,2,6,6-tetramethylpiperidine 在 苄基三乙基氯化铵 、 三乙胺 、 三氟乙酸 、 copper(I) bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 20.0~80.0 ℃ 、8.11 MPa 条件下， 反应 96.0h， 生成 Oxazolo[4,3-a]isoquinolin-3-one, 1,5,6,10b-tetrahydro-8,9-dimethoxy-10b-methyl-1,4'-spiro-(2,2,6,6-tetramethylpiperidine)-
  参考文献：
  名称：

  通过4-羟基恶唑烷酮-2-酮的分子内酰胺烷基化反应合成杂环顺式-β-氨基醇的前体

  摘要：

  DOI：

  10.1023/a:1002881002737
• 作为产物：
  描述：

  四甲基哌啶酮 、 乙炔 在 乙醚 、 氨 、 sodium amide 作用下， 生成 4-Ethynyl-4-hydroxy-2,2,6,6-tetramethylpiperidine
  参考文献：
  名称：

  161.哌啶系列实验。第四部分

  摘要：

  DOI：

  10.1039/jr9480000806

文献信息

• Synthesis of nitroxides using dioxiranes
  申请人：Curators of the University of Missouri

  公开号：US05087752A1

  公开（公告）日：1992-02-11

  The subject invention relates to a method of synthesizing nitroxides from secondary amines. This method uses a suitable dioxirane compound such as dimethyldioxirane (DMD), which is relatively stable and simple to synthesize, as the oxidizing agent. A quantity of a secondary amine having no hydrogen atoms directly attached to the alpha carbon atoms is mixed with a 2x molar ratio of the dioxirane. In a first reaction, the secondary amine is oxidized to form a hydroxylamine; in a second reaction, the hydroxylamine is further oxidized to form a nitroxide. When the dioxirane loses an oxygen atom it converts into a ketone; for example, dimethyldioxirane is converted into acetone. This is very convenient, since the ketone byproduct is a solvent that can be easily removed after the reaction without causing interfering reactions. This method provides a simple, highly selective, rapid reaction with very high yields. It can be carried out in a single reaction vessel and can be used with a wide variety of secondary amines (including secondary amines having more than one amine group) to create a corresponding variety of nitroxides.

  该专利涉及一种从二级胺合成亚硝基的方法。该方法使用适当的二氧环丙烷化合物，如二甲基二氧环丙烷（DMD），作为氧化剂，这种化合物相对稳定且易于合成。将一定量的二级胺与二氧环丙烷的2倍摩尔比混合。在第一反应中，二级胺被氧化形成羟胺；在第二反应中，羟胺进一步被氧化形成亚硝基。当二氧环丙烷失去一个氧原子时，它会转化为酮；例如，二甲基二氧环丙烷转化为丙酮。这非常方便，因为酮副产物是一种溶剂，在反应后可以很容易地去除而不引起干扰反应。该方法提供了一个简单、高度选择性、快速反应且产率非常高的方法。它可以在单个反应容器中进行，并可与各种二级胺（包括具有多个胺基的二级胺）一起使用，以创建相应多样的亚硝基。
• Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes
  作者：Denis S. Baranov、Anna S. Smorygina、Sergei A. Dzuba

  DOI：10.3390/molecules27134127

  日期：——

  be applied to study its interaction with biological membranes and proteins if its spin-labeled analogs were synthesized. Here, a simple sequence of ibuprofen transformations—nitration, esterification, reduction, Sandmeyer reaction, Sonogashira cross-coupling, oxidation and saponification—was developed to attain this goal. The synthesis resulted in spin-labeled ibuprofen (ibuprofen-SL) in which the spin

  布洛芬是一种非甾体抗炎药，具有镇痛和解热活性。如果合成了其自旋标记的类似物，则可以应用电子顺磁共振 (EPR) 光谱来研究其与生物膜和蛋白质的相互作用。在这里，开发了布洛芬转化的简单序列——硝化、酯化、还原、Sandmeyer 反应、Sonogashira 交叉偶联、氧化和皂化——来实现这一目标。该合成产生了自旋标记的布洛芬 (ibuprofen-SL)，其中自旋标记 TEMPOL 连接到苯环上。EPR 光谱证实了布洛芬-SL 与 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) 双层的相互作用。使用2H 电子自旋回波包络调制 (ESEEM) 光谱，发现布洛芬-SL 嵌入疏水双层内部。
• Hamill, Gregory P.; Yost, Elizabeth A.; Sandman, Daniel J., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1992, vol. 211, p. 339 - 346
  作者：Hamill, Gregory P.、Yost, Elizabeth A.、Sandman, Daniel J.

  DOI：——

  日期：——
• Zwitterionic copper(I) π-complexes with monosubstituted alkynes. Synthesis and X-ray diffraction study of a π-complex of copper(I) chloride with 4-ethynyl-4-hydroxy-2,2,6,6-tetramethylpiperidinium chloride
  作者：G. V. Noshchenko、B. M. Mykhalichko、V. N. Davydov

  DOI：10.1134/s0036023612010159

  日期：2012.1

  The first mononuclear pi-complex of copper(I) chloride with monosubstituted alkyne of the formula [(C9H16NH2(OH)C CH)CuCl2] was obtained in the system CuCl-HCl-H2O(C9H16NH2(OH)C CH)Cl (C9H16(OH)C CH is the 4-ethynyl-4-hydroxy-2,2,6,6-tetramethylpiperidinium cation) and studied by single-crystal X-ray and X-ray powder diffraction. The crystals are monoclinic: a = 16.868(8) angstrom, b = 13.177(8) angstrom, c = 13.32(1) angstrom, gamma = 103.50(4)degrees, space group P2(1)/b, Z = 8. The structure of the complex contains two crystallographically independent zwitterionic entities of the formula [(C9H16NH2(OH)C CH)CuCl2], which result from pi-coordination of the potential pi-bidentate bond C C of the organic cation to one Cu(I) atom of the inorganic anion. The distances Cu-m (m is the mid-point of the C C bond) are 1.91(2) angstrom. Along with weak intermolecular hydrogen bonds CH center dot center dot center dot Cl and intramolecular contacts OH center dot center dot center dot Cl, the structure is stabilized by a directed ionic interaction through strong NH center dot center dot center dot Cl bonds.
• SHAPIRO, A. B.;EHRMAN, M. B.;GULYJ, S. E.;KRAVCHENKO, Z. A.;AULCHENKO, I.+
  作者：SHAPIRO, A. B.、EHRMAN, M. B.、GULYJ, S. E.、KRAVCHENKO, Z. A.、AULCHENKO, I.+

  DOI：——

  日期：——