(R)-5-hydroxy-7-cyanohept-2-ynoic acid ethyl ester | 916489-09-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-5-hydroxy-7-cyanohept-2-ynoic acid ethyl ester
• 英文别名: ethyl (5R)-7-cyano-5-hydroxyhept-2-ynoate
• CAS: 916489-09-3
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: QMDQDUWFOJDECQ-VIFPVBQESA-N

物化性质

• 沸点：
  402.5±40.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-5-hydroxy-7-cyanohept-2-ynoic acid ethyl ester 在 Pt/Al₂O₃ 氢气 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， -30.0~20.0 ℃ 、344.74 kPa 条件下， 反应 25.17h， 生成 (4S,6R)-tetrahydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one
  参考文献：
  名称：

  Strategy for the Enantioselective Synthesis of trans-2,4-Disubstituted Piperidines:  Application to the CCR3 Antagonist IS811

  摘要：

  A strategy for the enantioselective synthesis of trans-2,4-disubstituted piperidines is proposed and applied to the preparation of IS811, a potent CCR3 antagonist. The C2 stereocenter is derived from commercial (R)-epichlorohydrin, while the C4 stereocenter is installed via diastereoselective hydrogenation of an alpha,beta-unsaturated lactone intermediate. Inversion of the original stereocenter via an efficient intramolecular S(N)2 amination affords the piperidine core of IS811. An improved protocol for the lithiation of ethyl propiolate is reported.

  DOI：

  10.1021/jo0616963
• 作为产物：
  描述：

  (R)-1,2-epoxy-4-cyanobutane 、 丙炔酸乙酯 在 正丁基锂 、 1-己炔 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.25h， 生成 (R)-5-hydroxy-7-cyanohept-2-ynoic acid ethyl ester
  参考文献：
  名称：

  Strategy for the Enantioselective Synthesis of trans-2,4-Disubstituted Piperidines:  Application to the CCR3 Antagonist IS811

  摘要：

  A strategy for the enantioselective synthesis of trans-2,4-disubstituted piperidines is proposed and applied to the preparation of IS811, a potent CCR3 antagonist. The C2 stereocenter is derived from commercial (R)-epichlorohydrin, while the C4 stereocenter is installed via diastereoselective hydrogenation of an alpha,beta-unsaturated lactone intermediate. Inversion of the original stereocenter via an efficient intramolecular S(N)2 amination affords the piperidine core of IS811. An improved protocol for the lithiation of ethyl propiolate is reported.

  DOI：

  10.1021/jo0616963

文献信息

• Strategy for the Enantioselective Synthesis of <i>trans</i>-2,4-Disubstituted Piperidines:  Application to the CCR3 Antagonist IS811
  作者：Goss S. Kauffman、Paul S. Watson、William A. Nugent

  DOI：10.1021/jo0616963

  日期：2006.11.1

  A strategy for the enantioselective synthesis of trans-2,4-disubstituted piperidines is proposed and applied to the preparation of IS811, a potent CCR3 antagonist. The C2 stereocenter is derived from commercial (R)-epichlorohydrin, while the C4 stereocenter is installed via diastereoselective hydrogenation of an alpha,beta-unsaturated lactone intermediate. Inversion of the original stereocenter via an efficient intramolecular S(N)2 amination affords the piperidine core of IS811. An improved protocol for the lithiation of ethyl propiolate is reported.