(1'S,2S)-2-<1'-<(methylsulfonyl)oxy>propen-2'-yl>-N-<(tert-butyloxy)carbonyl>pyrrolidine | 146880-59-3

• 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'-<(methylsulfonyl)oxy>propen-2'-yl>-N-<(tert-butyloxy)carbonyl>pyrrolidine
• 英文别名: (1'S,2S)-2-{1'-[(methylsulfonyl)oxy]propen-2'-yl}-N-[(tert-butyloxy)carbonyl]pyrrolidine；tert-butyl (2S)-2-[(1S)-1-methylsulfonyloxyprop-2-enyl]pyrrolidine-1-carboxylate
• CAS: 146880-59-3
• 化学式: C₁₃H₂₃NO₅S
• 分子量: 305.395
• InChiKey: OICFKHFNAIQSJO-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'S,2S)-2-<1'-<(methylsulfonyl)oxy>propen-2'-yl>-N-<(tert-butyloxy)carbonyl>pyrrolidine 在 臭氧 、 三苯基膦 作用下， 反应 3.17h， 生成 tert-butyl (2S)-2-[(E,3R)-3-methoxycarbonyl-4-methylpent-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 吡啶 、 4-二甲氨基吡啶 、 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 29.17h， 生成 (1'S,2S)-2-<1'-<(methylsulfonyl)oxy>propen-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

• 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.