[(2E)-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylpenta-2,4-dienoxy]-trimethylsilane | 154169-95-6

• 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: [(2E)-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylpenta-2,4-dienoxy]-trimethylsilane
• CAS: 154169-95-6
• 化学式: C₁₅H₂₉NO₂Si
• 分子量: 283.486
• InChiKey: VGYWTNRMJSMSGP-GLNPCMGASA-N

物化性质

• 沸点：
  354.5±25.0 °C(Predicted)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2E)-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylpenta-2,4-dienoxy]-trimethylsilane 在 碳酸氢钠 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (2R,3S,6S)-1-aza-3-methyl-6-phenyl-8-oxa-4,7-dioxobicyclo[4.3.0]nonane
  参考文献：
  名称：

  Barluenga, Jose; Aznar, Fernando; Ribas, Cristina, Chemistry - A European Journal, 1996, vol. 2, # 7, p. 805 - 811

  摘要：

  DOI：
• 作为产物：
  描述：

  3-methyl-5-[(trimethylsilyl)oxy]-3-penten-1-yne 、 (S)-(+)-2-(甲氧基甲基)吡唑烷 在 mercury(II) diacetate 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到[(2E)-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methylpenta-2,4-dienoxy]-trimethylsilane
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

  摘要：

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.

  DOI：

  10.1021/jo9722414

文献信息

• First [4 + 2] cycloaddition reaction between vinyl Fischer type carbene complexes and chiral 2-amino-1,3-dienes
  作者：José Barluenga、Fernando Aznar、Alfredo Martín、Soffía Barluenga、Santiago Garcíia-Granda、Armando A. Paneque-Quevedo

  DOI：10.1039/c39940000843

  日期：——

  The reaction between 2-aminobuta-1,3-dienes derived from (S)-2-methoxymethylpyrrolidine and vinyl Fischer type tungsten carbenes complexes leads to cyclohexeyl carbene complex derivatives with acceptable yields and good enantiomeric excess.

  (S)-2-甲氧基甲基吡咯烷衍生的2-氨基-1,3-丁二烯与乙烯基费歇尔型碳硼烷络合物之间的反应，可生成环己基碳硼烷络合物衍生物，收率可接受，且具有较好的对映体过剩。
• Barluenga, Jose; Aznar, Fernando; Ribas, Cristina, Chemistry - A European Journal, 1996, vol. 2, # 7, p. 805 - 811
  作者：Barluenga, Jose、Aznar, Fernando、Ribas, Cristina、Valdes, Carlos、Fernandez, Monica、et al.

  DOI：——

  日期：——
• Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives
  作者：José Barluenga、Fernando Aznar、Carlos Valdés、Cristina Ribas

  DOI：10.1021/jo9722414

  日期：1998.6.1

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.