methyl 1-allylpyrrolidine-2-carboxylate | 132910-67-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 1-allylpyrrolidine-2-carboxylate
• 英文别名: methyl N-allyl-2-pyrrolidinecarboxylate；Methyl 1-prop-2-enylpyrrolidine-2-carboxylate
• CAS: 132910-67-9
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: MZCQQCAGBZDISA-UHFFFAOYSA-N

物化性质

• 沸点：
  205.3±33.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-allylpyrrolidine-2-carboxylate 在 吡啶 、 sodium hydroxide 、 盐酸羟胺 、 二异丁基氢化铝 作用下， 以 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 20.08h， 生成 1-benzoyl-1,1a,3,3a-tetrahydropyrrolizidino<3,2-c>isoxazole
  参考文献：
  名称：

  Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations

  摘要：

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.

  DOI：

  10.1021/jo00008a038
• 作为产物：
  描述：

  DL-脯氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 19.0h， 生成 methyl 1-allylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations

  摘要：

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.

  DOI：

  10.1021/jo00008a038

文献信息

• Rhodium-catalysed isomerisation/formal 1,3-dipolar cycloaddition cascades to fused-ring heterocycles
  作者：Ryan M. Gorman、Marc A. Little、James A. Morris、Visuvanathar Sridharan

  DOI：10.1039/c2cc35372e

  日期：——

  Fused ring heterocycles were synthesised via the rhodium catalysed isomerisation/regio and stereoselective 1,3-dipolar cycloaddition cascades in good yields.

  稠环杂环被通过铑催化的合成异构化/区域选择性和立体选择性的1,3-偶极以良好的收率环加成级联。
• Pyrrolidone derivatives, oligomers and polymers
  申请人：NanoSynthons LLC

  公开号：US10968176B2

  公开（公告）日：2021-04-06

  Simple organic structures, organic/inorganic polymers, and other substrates have been made, all of which have at least one pyrrolidone moiety present, and found to exhibit low toxicity, low complement activation features and may be used to reduce protein interactions with drug conjugates while enhancing in vivo residency times for these conjugates when used as an injectable composition; thus these compounds can be used as substitutes for PEG in PEGylation. Surprisingly, these compounds also exhibit unique intrinsic fluorescence (IF) or non-traditional fluorescence (NTF) properties that currently cannot be explained by traditional photochemistry and fluorescence paradigms are described. These compounds have a variety of applications such as in cellular imaging, gene transfection, bio-diagnostics, biosensing, fluorescence directed surgical resections, drug delivery, forensics, environmental diagnostics, mineral/gemstone characterization, counterfeit goods detection, tracer studies related to liquid/water flow, oil field enhancements and diagnostics, prevention of photo-bleaching, and LED display enhancements and others.

  我们已经制备出了简单的有机结构、有机/无机聚合物和其他基质，所有这些基质都至少含有一个吡咯烷酮分子，并发现它们具有低毒性、低补体激活特性，可用于减少蛋白质与药物共轭物的相互作用，同时在用作注射组合物时可提高这些共轭物在体内的驻留时间；因此，这些化合物可在 PEG 化过程中用作 PEG 的替代品。令人惊奇的是，这些化合物还表现出独特的本征荧光（IF）或非传统荧光（NTF）特性，而这些特性目前还无法用传统的光化学和荧光范式来解释。这些化合物有多种应用，如细胞成像、基因转染、生物诊断、生物传感、荧光引导手术切除、给药、法医、环境诊断、矿物/宝石表征、假冒商品检测、与液体/水流有关的示踪研究、油田增强和诊断、防止光漂白、LED 显示屏增强等。
• HASSNER, ALFRED;MAURYA, RAKESH;PADWA, ALBERT;BULLOCK, WILLIAM H., J. ORG. CHEM., 56,(1991) N, C. 2775-2781
  作者：HASSNER, ALFRED、MAURYA, RAKESH、PADWA, ALBERT、BULLOCK, WILLIAM H.

  DOI：——

  日期：——
• PYRROLIDONE DERIVATIVES, OLIGOMERS AND POLYMERS
  申请人：NanoSynthons LLC

  公开号：US20190352258A1

  公开（公告）日：2019-11-21

  Simple organic structures, organic/inorganic polymers, and other substrates have been made, all of which have at least one pyrrolidone moiety present, and found to exhibit low toxicity, low complement activation features and may be used to reduce protein interactions with drug conjugates while enhancing in vivo residency times for these conjugates when used as an injectable composition; thus these compounds can be used as substitutes for PEG in PEGylation. Surprisingly, these compounds also exhibit unique intrinsic fluorescence (IF) or non-traditional fluorescence (NTF) properties that currently cannot be explained by traditional photochemistry and fluorescence paradigms are described. These compounds have a variety of applications such as in cellular imaging, gene transfection, bio-diagnostics, biosensing, fluorescence directed surgical resections, drug delivery, forensics, environmental diagnostics, mineral/gemstone characterization, counterfeit goods detection, tracer studies related to liquid/water flow, oil field enhancements and diagnostics, prevention of photo-bleaching, and LED display enhancements and others.
• Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations
  作者：Alfred Hassner、Rakesh Maurya、Albert Padwa、William H. Bullock

  DOI：10.1021/jo00008a038

  日期：1991.4

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.