(2R,4R)-2-tert-butyl 2-methyl 1,4-dimethyl-3-methylene-5-oxopyrrolidine-2,2-dicarboxylate | 1140895-33-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,4R)-2-tert-butyl 2-methyl 1,4-dimethyl-3-methylene-5-oxopyrrolidine-2,2-dicarboxylate
• 英文别名: 2-O'-tert-butyl 2-O-methyl (2R,4R)-1,4-dimethyl-3-methylidene-5-oxopyrrolidine-2,2-dicarboxylate
• CAS: 1140895-33-5
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: FVQANMKDSCHWGJ-XLKFXECMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-tert-butyl 2-methyl 1,4-dimethyl-3-methylene-5-oxopyrrolidine-2,2-dicarboxylate 在 zinc(II) tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以90%的产率得到(2R,4R)-tert-butyl 2-(hydroxymethyl)-1,4-dimethyl-3-methylene-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Efficient asymmetric synthesis of the functionalized pyroglutamate core unit common to oxazolomycin and neooxazolomycin using Michael reaction of nucleophilic glycine Schiff base with α,β-disubstituted acrylate

  摘要：

  The functionalized pyroglutamate core unit, (2R,4R)-3, which could be converted into the beta-lactone/pyrrolidine or gamma-lactone/pyrrolidine ring system of oxazolomycin A 1 and neooxazolomycin 2, and which possesses an exomethylene group at C3 as a scaffold for the Construction of their C3 polyene segment, was synthesized by the Michael reaction of a glycine Schiff base 4 with the alpha,beta-disubstituted acrylate 8 as the key step. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.036
• 作为产物：
  描述：

  (2R,3S,4R)-2-tert-butyl 2-methyl 1,4-dimethyl-5-oxo-3-((phenylselanyl)methyl)pyrrolidine-2,2-dicarboxylate 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以97%的产率得到(2R,4R)-2-tert-butyl 2-methyl 1,4-dimethyl-3-methylene-5-oxopyrrolidine-2,2-dicarboxylate
  参考文献：
  名称：

  Efficient asymmetric synthesis of the functionalized pyroglutamate core unit common to oxazolomycin and neooxazolomycin using Michael reaction of nucleophilic glycine Schiff base with α,β-disubstituted acrylate

  摘要：

  The functionalized pyroglutamate core unit, (2R,4R)-3, which could be converted into the beta-lactone/pyrrolidine or gamma-lactone/pyrrolidine ring system of oxazolomycin A 1 and neooxazolomycin 2, and which possesses an exomethylene group at C3 as a scaffold for the Construction of their C3 polyene segment, was synthesized by the Michael reaction of a glycine Schiff base 4 with the alpha,beta-disubstituted acrylate 8 as the key step. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.036

文献信息

• Efficient asymmetric synthesis of the functionalized pyroglutamate core unit common to oxazolomycin and neooxazolomycin using Michael reaction of nucleophilic glycine Schiff base with α,β-disubstituted acrylate
  作者：Takeshi Yamada、Kazuhiko Sakaguchi、Tetsuro Shinada、Yasufumi Ohfune、Vadim A. Soloshonok

  DOI：10.1016/j.tetasy.2008.11.036

  日期：2008.12

  The functionalized pyroglutamate core unit, (2R,4R)-3, which could be converted into the beta-lactone/pyrrolidine or gamma-lactone/pyrrolidine ring system of oxazolomycin A 1 and neooxazolomycin 2, and which possesses an exomethylene group at C3 as a scaffold for the Construction of their C3 polyene segment, was synthesized by the Michael reaction of a glycine Schiff base 4 with the alpha,beta-disubstituted acrylate 8 as the key step. (C) 2008 Elsevier Ltd. All rights reserved.