1-(PROP-2-EN-1-YL)PIPERIDINE-2-CARBALDEHYDE | 907188-84-5

• 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: 1-(PROP-2-EN-1-YL)PIPERIDINE-2-CARBALDEHYDE
• 英文别名: 1-Prop-2-enylpiperidine-2-carbaldehyde
• CAS: 907188-84-5
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: BPSWVEISMWGSQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(PROP-2-EN-1-YL)PIPERIDINE-2-CARBALDEHYDE 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 syn-1,1a,3,3a,4,5,6,7,8,8a-decahydropyridino<1,2-a>isoxazolo<3,4-c>pyrrole
  参考文献：
  名称：

  Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations

  摘要：

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.

  DOI：

  10.1021/jo00008a038
• 作为产物：
  描述：

  六氢吡啶-alpha-羧酸 在 lithium aluminium tetrahydride 、 氯化亚砜 、 草酰氯 、 ammonium chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 20.83h， 生成 1-(PROP-2-EN-1-YL)PIPERIDINE-2-CARBALDEHYDE
  参考文献：
  名称：

  A concise synthesis of (±) and a total synthesis of (+)-epiquinamide

  摘要：

  A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from (-)-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.092

文献信息

• HASSNER, ALFRED;MAURYA, RAKESH;PADWA, ALBERT;BULLOCK, WILLIAM H., J. ORG. CHEM., 56,(1991) N, C. 2775-2781
  作者：HASSNER, ALFRED、MAURYA, RAKESH、PADWA, ALBERT、BULLOCK, WILLIAM H.

  DOI：——

  日期：——
• A concise synthesis of (±) and a total synthesis of (+)-epiquinamide
  作者：Sok Teng (Amy) Tong、David Barker

  DOI：10.1016/j.tetlet.2006.05.092

  日期：2006.7

  A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from (-)-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.
• Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations
  作者：Alfred Hassner、Rakesh Maurya、Albert Padwa、William H. Bullock

  DOI：10.1021/jo00008a038

  日期：1991.4

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.