(3R,3aS,6aR)-tert-butyl hexahydro-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate | 1140895-31-3

• 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: (3R,3aS,6aR)-tert-butyl hexahydro-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate
• 英文别名: tert-butyl (3R,3aS,6aR)-1,3-dimethyl-2,6-dioxo-3a,4-dihydro-3H-furo[3,4-b]pyrrole-6a-carboxylate
• CAS: 1140895-31-3
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: MJJSHINRZNDHML-BFHDXFOESA-N

物化性质

• 沸点：
  430.1±45.0 °C(predicted)
• 密度：
  1.224±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  重氮甲烷 、 (3R,3aS,6aR)-tert-butyl hexahydro-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate 、 二苯基二硒醚 在 sodium tetrahydroborate 作用下， 以 乙醇 、 乙醚 为溶剂， 反应 0.5h， 以61%的产率得到(2R,3S,4R)-2-tert-butyl 2-methyl 1,4-dimethyl-5-oxo-3-((phenylselanyl)methyl)pyrrolidine-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
• 作为产物：
  描述：

  (2R,3S,4R)-2-(tert-butoxycarbonyl)-3-(hydroxymethyl)-1,4-dimethyl-5-oxopyrrolidine-2-carboxylic acid 在 重氮甲烷 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以50%的产率得到(3R,3aS,6aR)-tert-butyl hexahydro-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-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

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.