(2S,5S)-2-Hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester

• 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: (2S,5S)-2-Hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,5S)-2-ethenyl-5-(hydroxymethyl)pyrrolidine-1-carboxylate
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: BLXUQZXRGQGITM-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2-Hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 吡啶 、 正丁基锂 、 二氯二茂锆 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 生成 Carbamic acid, [(1R,3S)-3-ethenylcyclopentyl]-, 1,1-dimethylethyl ester, rel-
  参考文献：
  名称：

  New “Cp2Zr”-mediated ring transformations of 2-vinylheterocycles to carbocycles

  摘要：

  Novel ''Cp2Zr''-mediated ring transformations of 2-vinylheterocycles (1, 2) to carbocycles (3, 4, 5) were shown to proceed through an intramolecular allylation of Z-allylic zirconocene species to the epoxide or aziridine intermediate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00989-1
• 作为产物：
  描述：

  (2R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,5S)-2-Hydroxymethyl-5-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  New “Cp2Zr”-mediated ring transformations of 2-vinylheterocycles to carbocycles

  摘要：

  Novel ''Cp2Zr''-mediated ring transformations of 2-vinylheterocycles (1, 2) to carbocycles (3, 4, 5) were shown to proceed through an intramolecular allylation of Z-allylic zirconocene species to the epoxide or aziridine intermediate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00989-1

文献信息

• A novel method for chirospecific synthesis of 2,5-disubstituted pyrrolidines
  作者：N. André Sasaki、Isabelle Sagnard

  DOI：10.1016/s0040-4020(01)85236-4

  日期：1994.1

  One-pot ring formation using (R)-1 or (S)-1 as a nucleophile and homochiral glycidyl triflate (R)-2 or (S)-2 as an electrophile a pivotal intermediate 4 which can be transformed into a 2,5-disubstituted pyrrolidine with any desired stereochemistry at the C-2 and C-5 positions.

  一锅环的形成使用（R） - 1或（S） - 1作为亲核和纯手性缩水甘油基三氟甲磺酸酯（R） - 2或（S） - 2作为亲电子试剂的枢转中间体4可转化成2， 5-二取代的吡咯烷在C-2和C-5位置具有任何所需的立体化学。
• New “Cp2Zr”-mediated ring transformations of 2-vinylheterocycles to carbocycles
  作者：Yuji Hanzawa、Hiromichi Kiyono、Noriaki Tanaka、Takeo Taguchi

  DOI：10.1016/s0040-4039(97)00989-1

  日期：1997.6

  Novel ''Cp2Zr''-mediated ring transformations of 2-vinylheterocycles (1, 2) to carbocycles (3, 4, 5) were shown to proceed through an intramolecular allylation of Z-allylic zirconocene species to the epoxide or aziridine intermediate. (C) 1997 Elsevier Science Ltd.
• Stereoselective Zirconocene-mediated Ring Transformation of 2-Vinylhetero- cycles to Vinylcarbocycles
  作者：Yuji Hanzawa、Hiromichi Kiyono、Takeo Taguchi

  DOI：10.3987/com-03-s(p)8

  日期：——

  Stereoselective ring transformation of 2-vinylheterocycles to vinylcarbocycles was efficiently carried out by the use of a zirconocene equivalent ("Cp2Zr"). The transformation proceeded through an intramolecular allylation of Z-allylic zirconocene species to the epoxide or aziridine ring.