tert-butyl N-[(4S,4aR,8aS)-6-methylidene-1-oxo-4,4a,5,7,8,8a-hexahydro-3H-isochromen-4-yl]carbamate | 173143-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl N-[(4S,4aR,8aS)-6-methylidene-1-oxo-4,4a,5,7,8,8a-hexahydro-3H-isochromen-4-yl]carbamate
• CAS: 173143-24-3
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: WRXIXXFWPLOKFM-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(4S,4aR,8aS)-6-methylidene-1-oxo-4,4a,5,7,8,8a-hexahydro-3H-isochromen-4-yl]carbamate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  Internal activation of acrylate-type dienophiles for the Diels-Alder reaction. Stereoselective synthesis of conformationally constrained glutamate analogs

  摘要：

  The [4+2] cycloaddition reaction of the unreactive acrylate-type dienophiles such as 5a and 6a was accomplished by introducing an electronegative or electron-withdrawing group as the ester counterpart. Among them, the pentafluorophenyl (PFP) group was found to be an excellent ester counterpart in view of its rate acceleration and chemical stability under the reaction conditions. The C-13 NMR spectral data of the dienophiles with the PFP group suggested that the conjugated CC-double bond was strongly polarized. The internal activation was found to be effective for the related dienophile or other dienes, in particular, unstable to Lewis acid catalysts. A successful application of this method is demonstrated by the syntheses of conformationally restricted analogs of L-glutamate, 3 and 4. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00219-1
• 作为产物：
  描述：

  (1'S,2Z)-1,1,1,3,3,3-hexafluoroisopropyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate 在 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 72.0h， 生成 tert-butyl N-[(4S,4aR,8aS)-6-methylidene-1-oxo-4,4a,5,7,8,8a-hexahydro-3H-isochromen-4-yl]carbamate
  参考文献：
  名称：

  Internal activation of acrylate-type dienophiles for the Diels-Alder reaction. Stereoselective synthesis of conformationally constrained glutamate analogs

  摘要：

  The [4+2] cycloaddition reaction of the unreactive acrylate-type dienophiles such as 5a and 6a was accomplished by introducing an electronegative or electron-withdrawing group as the ester counterpart. Among them, the pentafluorophenyl (PFP) group was found to be an excellent ester counterpart in view of its rate acceleration and chemical stability under the reaction conditions. The C-13 NMR spectral data of the dienophiles with the PFP group suggested that the conjugated CC-double bond was strongly polarized. The internal activation was found to be effective for the related dienophile or other dienes, in particular, unstable to Lewis acid catalysts. A successful application of this method is demonstrated by the syntheses of conformationally restricted analogs of L-glutamate, 3 and 4. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00219-1