tert-butyl (3S,3aS,6aR)-3-(hydroxymethyl)spiro[1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-5,1'-cyclopropane]-2-carboxylate | 597569-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (3S,3aS,6aR)-3-(hydroxymethyl)spiro[1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-5,1'-cyclopropane]-2-carboxylate
• CAS: 597569-40-9
• 化学式: C₁₅H₂₅NO₃
• 分子量: 267.368
• InChiKey: VGXZMYOOEAOUGV-SDDRHHMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  tert-butyl (3S,3aS,6aR)-3-(hydroxymethyl)spiro[1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-5,1'-cyclopropane]-2-carboxylate 在 jones' reagent 作用下， 以 丙酮 为溶剂， 以100%的产率得到(3S,3aS,6aR)-2-[(2-methylpropan-2-yl)oxycarbonyl]spiro[1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-5,1'-cyclopropane]-3-carboxylic acid
  参考文献：
  名称：

  [3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates

  摘要：

  Unsaturated lactam derived from (S)-pyroglutaminol undergoes a totally stereoselective cycloaddition reaction with (2-(acetoxymethyl)-3-allyl)trimethylsilane in the presence of Pd(P(OiPr)(3))(4) in refluxing toluene. This step was efficiently used to introduced the 5,5-fused framework desired for the preparation of novel proline surrogates. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01191-2
• 作为产物：
  描述：

  (1S,2S,5R,8R)-10-methylidene-5-phenyl-4-oxa-6-azatricyclo[6.3.0.02,6]undecan-7-one 在 lithium aluminium tetrahydride 、 diethylzinc 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 tert-butyl (3S,3aS,6aR)-3-(hydroxymethyl)spiro[1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-5,1'-cyclopropane]-2-carboxylate
  参考文献：
  名称：

  [3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates

  摘要：

  Unsaturated lactam derived from (S)-pyroglutaminol undergoes a totally stereoselective cycloaddition reaction with (2-(acetoxymethyl)-3-allyl)trimethylsilane in the presence of Pd(P(OiPr)(3))(4) in refluxing toluene. This step was efficiently used to introduced the 5,5-fused framework desired for the preparation of novel proline surrogates. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01191-2