(-)-menthone nitrone | 188858-92-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-menthone nitrone
• 英文别名: 6-isopropyl-4,9-dimethyl-3-oxo-1,4-diazaspiro[4.5]dec-1-ene 1-oxide；(5S,6S,9R)-6-isopropyl-4,9-dimethyl-1,4-diazaspiro[4.5]dec-1-en-3-one 1-oxide；(5S,6S,9R)-1,9-dimethyl-4-oxido-6-propan-2-yl-1-aza-4-azoniaspiro[4.5]dec-3-en-2-one
• CAS: 188858-92-6
• 化学式: C₁₃H₂₂N₂O₂
• 分子量: 238.33
• InChiKey: GYGJMCPUOGIUAN-MDZLAQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-menthone nitrone 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 38.0h， 生成 (3S,5R,6S,9R)-3-[(S)-2-Hydroxy-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-6-isopropyl-1,9-dimethyl-1,4-diaza-spiro[4.5]decan-2-one
  参考文献：
  名称：

  Chiral Auxiliary Based Approach Toward the Synthesis of C-Glycosylated Amino Acids

  摘要：

  [GRAPHICS]In a chiral auxiliary based method C-glycosylated amino acids can be obtained by a 1,3-dipolar cycloaddition of a chiral glycine equivalent and C-1 allyl- or vinyl-derived carbohydrate building blocks as the key step. The products are formed regio- and diastereoselectively. Reductive cleavage of the N-O bond of the isoxazolidine and of the chiral auxiliary leads to C-glycosylated amino acids. The use of (-)-menthone to (+)-menthone as the auxiliary leads to the corresponding diastereomers.

  DOI：

  10.1021/ol015743j
• 作为产物：
  描述：

  (-)-薄荷酮 、 甘氨酸甲酯盐酸盐 、 甲胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 32.0h， 以89%的产率得到(-)-menthone nitrone
  参考文献：
  名称：

  涉及环硝基的1,3-偶极环加成反应的受限C-糖基氨基酸衍生物的合成为关键步骤

  摘要：

  遵循两步策略，其中一个步骤是分离构象受限的C-糖基氨基酸衍生物，该策略涉及在L -（-）-薄荷酮衍生的硝酮和C-乙烯基糖苷之间进行1,3-偶极环加成，这是关键步骤。环加成反应具有高度的区域选择性和立体选择性，可导致相应的环加合物高产。简单拆分手性助剂可以制备C-糖基氨基酸类似物。

  DOI：

  10.1002/ejoc.202001162

文献信息

• Unprecedented stereoselective synthesis of 3-methylisoxazolidine-5-aryl-1,2,4-oxadiazoles via 1,3-dipolar cycloaddition and study of their in vitro antioxidant activity
  作者：Jihed Brahmi、Siwar Ghannay、Sana Bakari、Kaïss Aouadi、Adel Kadri、Moncef Msaddek、Sébastien Vidal

  DOI：10.1080/00397911.2016.1244692

  日期：2016.12.16

  ABSTRACT The stereoselective 1,3-dipolar cycloaddition between allyl cyanide and a menthone-derived nitrone led to the desired isoxazolidine in good yield. Once the nitrile group transformed to an amidoxime group, the cyclocondensation of various aldehydes with chiral amidoxime led to unprecedented enantiopure 3-methylisoxazolidine-5-aryl-1,2,4-oxadiazoles. The menthone chiral auxiliary was then removed

  摘要烯丙基氰化物和薄荷酮衍生的硝酮之间的立体选择性 1,3-偶极环加成以良好的收率获得了所需的异恶唑烷。一旦腈基转变为胺肟基团，各种醛与手性胺肟的环缩合反应产生了前所未有的对映体纯 3-甲基异恶唑烷-5-芳基-1,2,4-恶二唑。然后通过酸水解除去薄荷酮手性助剂。还使用 DPPH 和 FRAP 分析筛选了新化合物的体外抗氧化活性。一些化合物显示出有希望的抗氧化活性。图形概要
• NOVEL PYRROLIDINE DERIVATIVES
  申请人：UNIVERSITE CLAUDE BERNARD LYON I

  公开号：US20150175537A1

  公开（公告）日：2015-06-25

  The present invention relates to novel pyrrolidine derivatives of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 and X are as defined in claim 1 , optionally in a zwitterionic form, in the form of a pure optical isomer, or in the form of a mixture of optical isomers in any proportions, or in a form enriched with an optical isomer, as well as their pharmaceutically acceptable salts, solvates or hydrates, and pharmaceutical compositions containing such compounds. These compounds are notably useful for treating, in particular in human beings, epilepsy, ischemia, neurodegenerative diseases such as Parkinson's disease or Huntington's chorea, multiple sclerosis, Devic's disease, Alzheimer's disease, psychiatric diseases such as schizophrenia, depression, addiction, allodynia and hyperalgia.

  本发明涉及公式(I)的新型吡咯烷衍生物：其中R1、R2、R3、R4、R5和X如权利要求书中定义的，可选地为带电离形式，以纯的光学异构体形式、或以任何比例的光学异构体混合物形式、或以富含光学异构体的形式存在，以及它们的药学上可接受的盐、溶剂合物或水合物，以及含有这些化合物的药物组合物。这些化合物特别适用于治疗，特别是在人类中，癫痫、缺血、帕金森病或亨廷顿舞蹈病等神经退行性疾病、多发性硬化症、德维克病、阿尔茨海默病、精神疾病如精神分裂症、抑郁症、成瘾、痛觉过敏和疼痛过敏。
• Stereoselective synthesis of enantiopure N -substituted pyrrolidin-2,5-dione derivatives by 1,3-dipolar cycloaddition and assessment of their in vitro antioxidant and antibacterial activities
  作者：Siwar Ghannay、Sana Bakari、Ameni Ghabi、Adel Kadri、Moncef Msaddek、Kaïss Aouadi

  DOI：10.1016/j.bmcl.2017.04.044

  日期：2017.6

  of the nitrone. The obtaining heterocycles were screened for their in vitro antioxidant properties and the results revealed that the potent antioxidant activity was generally recorded to compounds (3g) and (3e). The in vitro antibacterial activities of these two compounds were also investigated and the results demonstrated the strongest potential of compound (3g) against all the tested bacteria. Molecular

  手性硝酮与N-取代的马来酰亚胺之间的1,3-偶极环加成反应以高收率和高对映选择性和非对映选择性提供了空前的对映纯螺环稠合杂环。反应在受阻较小的硝酮表面上进行。筛选获得的杂环的体外抗氧化性能，结果表明，强抗氧化活性通常记录在化合物（3g）和（3e）中。还研究了这两种化合物的体外抗菌活性，结果证明了该化合物（3g）对所有测试细菌的最强潜力。分析了分子性质，并显示了良好的口服候选药物（如性质），可以用作潜在的抗氧化剂和抗菌剂。最后，
• Stereoselective synthesis of 1,2,3-triazolyl-functionalized isoxazolidines, via two consecutive 1,3-dipolar cycloadditions, as precursors of unnatural amino acids
  作者：Kaïss Aouadi、Sébastien Vidal、Moncef Msaddek、Jean-Pierre Praly

  DOI：10.1016/j.tetlet.2013.01.125

  日期：2013.4

  isoxazolidines, which were isolated in modest yields. For a general and reliable access to 5-(triazolyl)methyl-substituted isoxazolidines, which are new compounds and valuable precursors of unnatural amino acids, performing the CuAAC cycloaddition as the final step is recommended.

  在微波辐射下，将（-）-薄荷酮衍生的硝酮与烯丙基溴进行1,3-偶极环加成，立体选择性地得到相应的手性异恶唑烷，收率为98％。用叠氮化物基团取代溴原子后（收率98％），另一种由各种炔烃进行的1,3-环加成反应生成了一系列1,2,3-三唑基官能化的异恶唑烷（收率约85％）。在酸催化下除去手性助剂似乎是迈向5取代的异恶唑烷的限制步骤，后者以适度的收率分离。为了普遍可靠地获得5-（三唑基）甲基取代的异恶唑烷，它们是新化合物和非天然氨基酸的宝贵前体，建议将CuAAC环加成作为最后一步。
• Cycloadditions of Chiral Nitrones to Racemic 3-Substituted Butenes: A Direct Access with Kinetic Resolution to Enantiopure Dihydroxylated Amino Acids
  作者：Jean-Pierre Praly、Kaiss Aouadi、Sébastien Vidal、Moncef Msaddek

  DOI：10.1055/s-2006-951534

  日期：——

  1,3-Dipolar cycloadditions of racemic 3-substituted 1-butenes to nitrones derived from (-)- or (+)-menthone occurred via exo-approach of the alkene onto the nitrone's less hindered face. This process afforded bicyclic spirpheterocycles as epimers, with selectivities ≤ 4:1, depending on the 3-substituent (R) on the alkene. The selectivity appeared to be influenced by hydrogen bonding (R = OH) or the

  外消旋 3-取代的 1-丁烯与衍生自 (-)- 或 (+)-薄荷酮的硝酮的 1,3-偶极环加成反应是通过烯烃在硝酮受阻较小的面上的外向途径发生的。该过程提供双环螺环作为差向异构体，选择性≤ 4:1，取决于烯烃上的 3-取代基 (R)。作为动力学拆分的结果，选择性似乎受到氢键 (R = OH) 或 R 基团的体积 (R = OBz, Br) 的影响。在手性助剂的还原步骤和裂解之后，获得的环加合物以高总产率得到对映纯的二羟基化非天然氨基酸。