(1'S,2S)-2-(1'-hydroxypropen-2'-yl)-N-<(tert-butyloxy)carbonyl>pyrrolidine | 146880-56-0

• 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: (1'S,2S)-2-(1'-hydroxypropen-2'-yl)-N-<(tert-butyloxy)carbonyl>pyrrolidine
• 英文别名: (1S,2S)-2-(1-hydroxyallyl)pyrrolidine-1-carboxylic acid tert-butyl ester；(1'S,2S)-2-(1'-hydroxypropen-2'-yl)-N-[(tert-butyloxy)carbonyl]pyrrolidine；tert-butyl (2S)-2-[(1S)-1-hydroxyprop-2-enyl]pyrrolidine-1-carboxylate
• CAS: 146880-56-0
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: IIFNJURKGMVLSF-UWVGGRQHSA-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：

  (1'S,2S)-2-(1'-hydroxypropen-2'-yl)-N-<(tert-butyloxy)carbonyl>pyrrolidine 在 吡啶 、 4-二甲氨基吡啶 、 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 15.17h， 生成 tert-butyl (2S)-2-[(E)-4-methoxy-4-oxobut-1-enyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Syn-SN2' pathway in the reaction of certain .gamma.-(mesyloxy) .alpha.,.beta.-enoates with RCu(CN)MgX.BF3 reagents. Importance of MgX and bulky R group upon the diastereoselectivity

  摘要：

  The reactions of protected serine- and threonine-derived gamma-(mesyloxy) alpha,beta-unsaturated esters with various magnesio organocyanocopper Lewis acid complexes have been investigated. The formation of syn-S(N)2' products, in addition to the normally expected anti-S(N)2' products, is taken as an indication that the reaction proceeds by a mechanism involving coordination of the magnesiocuprate with the C(delta)-N:C(gamma)-O syn-gamma-(mesyloxy) alpha,beta-enoates.

  DOI：

  10.1021/jo00057a038
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 sodium tetrahydroborate 、 pyridine-SO3 complex 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 17.17h， 生成 (1'S,2S)-2-(1'-hydroxypropen-2'-yl)-N-<(tert-butyloxy)carbonyl>pyrrolidine
  参考文献：
  名称：

  Syn-SN2' pathway in the reaction of certain .gamma.-(mesyloxy) .alpha.,.beta.-enoates with RCu(CN)MgX.BF3 reagents. Importance of MgX and bulky R group upon the diastereoselectivity

  摘要：

  The reactions of protected serine- and threonine-derived gamma-(mesyloxy) alpha,beta-unsaturated esters with various magnesio organocyanocopper Lewis acid complexes have been investigated. The formation of syn-S(N)2' products, in addition to the normally expected anti-S(N)2' products, is taken as an indication that the reaction proceeds by a mechanism involving coordination of the magnesiocuprate with the C(delta)-N:C(gamma)-O syn-gamma-(mesyloxy) alpha,beta-enoates.

  DOI：

  10.1021/jo00057a038

文献信息

• Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine
  作者：Sally J. Oxenford、Stephen P. Moore、Giorgio Carbone、Graeme Barker、Peter O’Brien、Mark R. Shipton、John Gilday、Kevin R. Campos

  DOI：10.1016/j.tetasy.2010.03.048

  日期：2010.6

  opening of aziridinium ions with MeNH2 as a route to chiral diamines has been explored. When the aziridinium ion contained a phenyl or para-methoxyphenyl substituent, stereospecific ring opening occurred. In contrast, switching the para-methoxy group to a para-N,N-dimethylamino group gave a racemic diamine product. Second, starting from N-Boc pyrrolidine, asymmetric lithiation-trapping-ring expansion (via

  描述了在两个不同项目中使用叠氮鎓离子。首先，已经探索了以MeNH 2为手性二胺的途径的叠氮鎓离子开环的立体特异性。当叠氮鎓离子包含苯基或对-甲氧基苯基取代基时，发生立体有择的开环。与此相反，在切换对位-甲氧基组到第- Ñ，Ñ二甲氨基基团，得到一个外消旋二胺产物。第二，从N -Boc吡咯烷开始，使用不对称的锂捕获-环扩环（通过叠氮鎓离子）来合成哌啶醇。这样，（-）的形式综合-swainsonine已完成。
• Functional Analysis of an Aspartate-Based Epoxidation Catalyst with Amide-to-Alkene Peptidomimetic Catalyst Analogues
  作者：Charles E. Jakobsche、Gorka Peris、Scott J. Miller

  DOI：10.1002/anie.200802223

  日期：2008.8.18
• Ibuka Toshiro, Taga Tooru, Habashita Hiromu, Nakai Kazuo, Tamamura Hiroka+, J. Org. Chem, 58 (1993) N 5, S 1207-1214
  作者：Ibuka Toshiro, Taga Tooru, Habashita Hiromu, Nakai Kazuo, Tamamura Hiroka+

  DOI：——

  日期：——
• Syn-SN2' pathway in the reaction of certain .gamma.-(mesyloxy) .alpha.,.beta.-enoates with RCu(CN)MgX.BF3 reagents. Importance of MgX and bulky R group upon the diastereoselectivity
  作者：Toshiro Ibuka、Tooru Taga、Hiromu Habashita、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yukiyasu Chounan、Hisao Nemoto、Yoshinori Yamamoto

  DOI：10.1021/jo00057a038

  日期：1993.2

  The reactions of protected serine- and threonine-derived gamma-(mesyloxy) alpha,beta-unsaturated esters with various magnesio organocyanocopper Lewis acid complexes have been investigated. The formation of syn-S(N)2' products, in addition to the normally expected anti-S(N)2' products, is taken as an indication that the reaction proceeds by a mechanism involving coordination of the magnesiocuprate with the C(delta)-N:C(gamma)-O syn-gamma-(mesyloxy) alpha,beta-enoates.