(R)-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide | 199386-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (R)-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide
• 英文别名: (R)-3,4-dihydro-2,5-dimethyl-5H-pyrrole 1-oxide；3,4-dihydro-2,5-dimethyl-2H-pyrrole 1-oxide；(2R)-2,5-dimethyl-1-oxido-3,4-dihydro-2H-pyrrol-1-ium
• CAS: 199386-10-2
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: QZIQCGJHQODACE-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (R)-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Characterization of the Crystalline Nature of the Racemates of Novel Chiral Five-Membered Cyclic Nitroxides

  摘要：

  Racemic samples of chiral five-membered cyclic nitroxides, 2,2,5,5-tetrasubstituted pyrrolidine-1-oxyls bearing one or two 4-hydroxyphenyl groups on the stereogenic centers [C(2) or C(2) & C(5)] adjacent to the NO radical moiety, exist as a racemic conglomerate in the crystalline state, whereas those having one or two 3-hydroxyphenyl groups at the same positions belong to a racemic compound. The key intermolecular interactions in controlling whether these racemates crystallize in a homochiral way or a heterochiral manner have been investigated by X-ray crystallographic analysis and magnetic susceptibility measurements.

  DOI：

  10.1080/15421400590957602
• 作为产物：
  描述：

  (2R,5R)-(-)-反-2,5-二甲基吡咯烷 在 双氧水 、 甲基三氧化铼(VII) 、 尿素 作用下， 以 甲醇 为溶剂， 以60%的产率得到(R)-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide
  参考文献：
  名称：

  Characterization of the Crystalline Nature of the Racemates of Novel Chiral Five-Membered Cyclic Nitroxides

  摘要：

  Racemic samples of chiral five-membered cyclic nitroxides, 2,2,5,5-tetrasubstituted pyrrolidine-1-oxyls bearing one or two 4-hydroxyphenyl groups on the stereogenic centers [C(2) or C(2) & C(5)] adjacent to the NO radical moiety, exist as a racemic conglomerate in the crystalline state, whereas those having one or two 3-hydroxyphenyl groups at the same positions belong to a racemic compound. The key intermolecular interactions in controlling whether these racemates crystallize in a homochiral way or a heterochiral manner have been investigated by X-ray crystallographic analysis and magnetic susceptibility measurements.

  DOI：

  10.1080/15421400590957602

文献信息

• A Practical Oxidative Method for the Cleavage of Hydrazide NN Bonds
  作者：Rosario Fernández、Ana Ferrete、José M. Llera、Antonio Magriz、Eloísa Martín-Zamora、Elena Díez、José M. Lassaletta

  DOI：10.1002/chem.200305501

  日期：2004.2.6

  hydrazide, without detection of the expected hydrazide N-oxides. In addition, the over oxidation of 26 into nitronate 25 proceeds through an unknown intermediate. This oxidative N[bond]N bond cleavage by peracids is an alternative method for the deamination of hydrazides, and constitutes the only solution compatible with substrates carrying functionalities sensitive to reducing conditions.

  酰肼中最亲核的氨基氮原子的选择性N-氧化对于开发在氧化条件下裂解其N [N] N键的前所未有的方法至关重要。用过酸如单过氧邻苯二甲酸镁六水合物（MMPP.6 H（2）O）或间氯过苯甲酸（m-CPBA）处理一系列酰肼1-9，可获得相应的酰胺10-16，收率良好。 （80-92％）。还研究了将该方法扩展至类似氨基甲酸酯的底物，例如17和18，但是在这种情况下，鉴于观察到的氨基甲酸酯19和20的产率低（约15％），该方法在合成上是无用的。从二烷基氨基部分开始，以等量的氧化剂产生的硝酮（例如26）进行了实验，（1）1 H NMR实验表明，该产物是通过母体酰肼的快速转化而形成的，而未检测到预期的酰肼N-氧化物。另外，通过未知的中间体将26过度氧化为亚硝酸盐25。过酸的这种氧化N [N] N键断裂是酰肼脱氨基的另一种方法，并且是与具有对还原条件敏感的官能团的底物相容的唯一溶液。
• Preparation and Ferroelectric Properties of New Chiral Liquid Crystalline Organic Radical Compounds
  作者：Rui Tamura、Naohiko Ikuma、Katsuaki Suzuki、Yoshiaki Uchida、Yoshio Aoki、Hiroyuki Nohira

  DOI：10.3987/com-09-s(s)64

  日期：——

  synthesized new chiral liquid crystalline (LC) organic radical compounds 2 and 3, which are the derivatives of the previously reported compounds 1 containing a chiral cyclic nitroxide unit and an ester group in the mesogen core, and their ferroelectric properties have been studied. The enantiomerically enriched (2S,5S)-2 and (2S,5S)-3 showed an SmC * phase for which their ferroelectric properties such as spontaneous

  我们合成了新的手性液晶（LC）有机自由基化合物 2 和 3，它们是先前报道的化合物 1 的衍生物，它们在介晶核中含有一个手性环状硝基氧单元和一个酯基，并对其铁电性能进行了研究。对映体富集的 (2S,5S)-2 和 (2S,5S)-3 显示出 SmC * 相，将它们的铁电特性如自发极化 (Ps) 和倾斜角 (θ) 与 (2S,5S) 进行了比较)-1。
• Through-Space Magnetic Interaction of <i>cis</i>-Azobenzene Biradical
  作者：Yoshiaki Uchida、Kenjiro Hino、Tatsuhisa Kato、Rui Tamura

  DOI：10.1021/acs.cgd.2c01247

  日期：2023.3.1

  Two chiral PROXYL groups bridged with azobenzene show the change of the magnetic properties with the trans-cis photoisomerization of the azobenzene moiety. The isomerization brought the radicals closer together and increased the exchange interactions. The spin state of the cis-isomer was determined from two-dimensional nutation spectra as a mixture of S = 1/2 and S = 1. This is an example of the optical control of through-space intramolecular magnetic interactions.

  与偶氮苯桥接的两个手性 PROXYL 基团显示了偶氮苯分子的反式-顺式光异构化所带来的磁性变化。异构化使两个基团靠得更近，增加了交换相互作用。顺式异构体的自旋态是由 S = 1/2和 S = 1 的混合物组成的，这是光控制的一个例子。这是通过空间分子内磁性相互作用进行光学控制的一个实例。
• Alternate Self-Regeneration of Stereocenters:  Enantioselective Generation of a <i>C</i>₂-Symmetric Chiral Nitroxide and Its Reduction to the Corresponding, Highly Sterically Hindered Amine
  作者：Jacques Einhorn、Cathy Einhorn、Fabien Ratajczak、Isabelle Gautier-Luneau、Jean-Louis Pierre

  DOI：10.1021/jo971812p

  日期：1997.12.1
• N,N-Dialkylhydrazones as the Imine Component in the Staudinger-Like [2+2] Cycloaddition to Benzyloxyketene We thank the Dirección General de Investigación Científica y Técnica (grants BQU 2001-2376 and PPQ 2000-1341) and the Junta de Andalucía for financial support. We also thank the Ministerio de Educación y Ciencia for a doctoral fellowship to A.F.
  作者：Rosario Fernández、Ana Ferrete、José M. Lassaletta、José M. Llera、Eloísa Martín-Zamora

  DOI：10.1002/1521-3773(20020301)41:5<831::aid-anie831>3.0.co;2-6

  日期：2002.3.1