tert-butyl (2S)-2-formyl-3,6-dihydro-2H-pyridine-1-carboxylate | 417726-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl (2S)-2-formyl-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 417726-35-3
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: GZCYIYZDNRTSCE-VIFPVBQESA-N

物化性质

• 沸点：
  294.6±40.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-formyl-3,6-dihydro-2H-pyridine-1-carboxylate 在 sodium chlorite 、 sodium dihydrogenphosphate 作用下， 以 水 、 叔丁醇 为溶剂， 以81%的产率得到(S)-N-BOC-1,2,3,6-四氢-2-吡啶羧酸
  参考文献：
  名称：

  Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain

  摘要：

  New enantioselective syntheses of N-protected baikiain and pipecolic acid have been developed. The starting material is 2,3-epoxy-5-hexen-1-ol (4) readily available in high ee by Sharpless epoxidation. The regio- and stereoselective epoxide ring-opening by allylamine afforded a doubly unsaturated amine that was converted into a carbamate (Boc) and submitted to ring-closing metathesis. The resulting cyclic amino diol 6 is a key intermediate that was converted into N-Boc-baikiain and several pipecolic acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02271-7
• 作为产物：
  描述：

  (2S,3S)-N-allyl-N-tert-butoxycarbonyl-3-amino-5-hexen-1,2-diol 在 Grubbs catalyst first generation sodium periodate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 tert-butyl (2S)-2-formyl-3,6-dihydro-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain

  摘要：

  New enantioselective syntheses of N-protected baikiain and pipecolic acid have been developed. The starting material is 2,3-epoxy-5-hexen-1-ol (4) readily available in high ee by Sharpless epoxidation. The regio- and stereoselective epoxide ring-opening by allylamine afforded a doubly unsaturated amine that was converted into a carbamate (Boc) and submitted to ring-closing metathesis. The resulting cyclic amino diol 6 is a key intermediate that was converted into N-Boc-baikiain and several pipecolic acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02271-7