[(S)-2-methoxymethylpyrrolidin-1-yl]-N-propylideneamine | 70113-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: [(S)-2-methoxymethylpyrrolidin-1-yl]-N-propylideneamine
• 英文别名: SAMP-hydrazone propionate；N-[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]propan-1-imine；N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]propan-1-imine
• CAS: 70113-32-5
• 化学式: C₉H₁₈N₂O
• 分子量: 170.255
• InChiKey: RDCLGPWIAPOWIC-VIFPVBQESA-N

物化性质

• 沸点：
  235.7±32.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(S)-2-methoxymethylpyrrolidin-1-yl]-N-propylideneamine 在 臭氧 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-N-Nitroso-O-methylprolinol
  参考文献：
  名称：

  Asymmetric Michael additions via SAMP-/RAMP-hydrazones anti-diastereo- and enantioselective synthesis of 3,4-disubstituted 5-oxo-alkanoates

  摘要：

  DOI：

  10.1016/s0040-4039(00)84830-3
• 作为产物：
  描述：

  (S)-N-Nitroso-O-methylprolinol 在 lithium aluminium tetrahydride 作用下， 生成 [(S)-2-methoxymethylpyrrolidin-1-yl]-N-propylideneamine
  参考文献：
  名称：

  Asymmetric Michael additions via SAMP-/RAMP-hydrazones anti-diastereo- and enantioselective synthesis of 3,4-disubstituted 5-oxo-alkanoates

  摘要：

  DOI：

  10.1016/s0040-4039(00)84830-3

文献信息

• Total Syntheses of Epothilones A and B via a Macrolactonization-Based Strategy
  作者：K. C. Nicolaou、S. Ninkovic、F. Sarabia、D. Vourloumis、Y. He、H. Vallberg、M. R. V. Finlay、Z. Yang

  DOI：10.1021/ja971110h

  日期：1997.8.1

  The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9−12 and 15 were constructed by asymmetric processes and coupled via

  描述了埃坡霉素 A (1) 和 B (2) 及其几种类似物的全合成。报道的策略依赖于大环内酯化方法，并分别具有前体 3 和 4 中大环双键的选择性环氧化（方案 1），以及高收敛性和灵活性。构建块 9-12 和 15 是通过不对称过程构建的，并通过 Wittig、羟醛和大环内酯化反应偶联，以相对较短的路线提供埃坡霉素及其几种类似物的基本骨架。利用通过立体选择性 Wittig 反应获得的中间体 14 及其与 SAMP 腙13 的 Enders 偶联（方案 8），
• First asymmetric synthesis of (un)substituted bridged tetrahydro-2-benzazepines
  作者：David Dumoulin、Stéphane Lebrun、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1016/j.tetasy.2009.12.026

  日期：2010.2

  A new and flexible route for the asymmetric synthesis of a variety of alkylated bridged tetrahydro-2-benzazepines has been developed. The key steps are the highly diastereoselective Michael addition of metalated SAMP-hydrazones to α,β-unsaturated esters combined with cyclomethylenation/Mitsunobu coupling reactions to secure the formation of the seven-membered azaheterocycle and of the bridged unit

  已开发出一种新的灵活途径，用于不对称合成各种烷基化的桥连四氢-2-苯并ze庚因。关键步骤是将金属化的SAMP hydr高度非对映选择性的迈克尔加成到α，β-不饱和酯上，并结合环甲基化/ Mitsunobu偶联反应以分别确保七元氮杂杂环和桥接单元的形成。
• Asymmetric synthesis of ?-(heteroaryl)alkylamines and ?-amino acids via nucleophilic 1,2-addition of lithiated heterocycles to aldehyde SAMP-hydrazones
  作者：DIETER ENDERS

  DOI：10.3906/kim-1302-71

  日期：——

  The asymmetric synthesis of \alpha-(heteroaryl)alkylamines was accomplished by employing a diastereoselective nucleophilic 1,2-addition of lithiated aromatic heterocycles to aldehyde SAMP-hydrazones, followed by BH_3 . THF or SmI_2 promoted removal of the chiral auxiliary. The CBz or benzoyl-protected amines were obtained in good yields (40\%--78\%) and excellent enantiomeric excesses (ee = 88\%--99\%). The methodology can be applied to the synthesis of highly enantioenriched \alpha-amino acids (ee = 90\%--99\%).

  第 V 组金属化合物与三氧化硫的反应
• Total synthesis of Epothilone E and related side-chain modified analogues via a stille coupling based strategy1This paper is dedicated with admiration and respect to the memory of Sir Derek H. R. Barton.1
  作者：K.C. Nicolaou、N.P. King、M.R.V. Finlay、Y. He、F. Roschangar、D. Vourloumis、H. Vallberg、F. Sarabia、S. Ninkovic、D. Hepworth

  DOI：10.1016/s0968-0896(98)00153-9

  日期：1999.5

  A Stille coupling strategy has been utilized to complete a total synthesis of epothilone E from vinyl iodide 7 and thiazole-stannane 8h. The central core fragment 7 and its trans-isomer 11 were prepared from triene 15 using ring-closing metathesis (RCM), and were subsequently coupled to a variety of alternative stannanes to provide a library of epothilone analogues 18a-o and 19a-o. The Stille coupling

  已利用Stille偶联策略完成了从乙烯基碘7和噻唑-锡烷8h合成埃博霉素E的全过程。使用闭环复分解（RCM）由三烯15制备中心核心片段7及其反式异构体11，随后将其与多种替代的锡烷偶联以提供埃坡霉素类似物18a-o和19a-o的文库。然后使用Stille偶联方法从关键的大内酯中间体24制备埃博霉素B类似物，该中间体本身是通过基于大内酯化的策略合成的。
• Total synthesis of 26-hydroxy-epothilone B and related analogs via a macrolactonization based strategy
  作者：K.C. Nicolaou、M.Ray V. Finlay、Sacha Ninkovic、Francisco Sarabia

  DOI：10.1016/s0040-4020(98)00352-4

  日期：1998.6

  The chemical synthesis of a series of 26-substituted epothilones B is described. Fully protected 26-hydroxydesoxy-epothilone B (7), prepared via the macrolactonization strategy, served as a common precursor to the designed epothilones described. The synthesized compounds were members of a large epothilone library whose biological screening led to the identification of a number of highly potent antitumor

  描述了一系列26个取代的埃坡霉素B的化学合成。通过大内酯化策略制备的完全保护的26-羟基脱氧-埃博霉素B（7），是上述设计埃博霉素的常见前体。合成的化合物是一个大型埃博霉素文库的成员，该库的生物学筛选可鉴定出许多高效的抗肿瘤药。