(R)-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one | 144409-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (R)-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one
• 英文别名: (9aR)-1,6,7,8,9,9a-hexahydroquinolizin-2-one
• CAS: 144409-59-6
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: UAOUQBPHAGQRIA-MRVPVSSYSA-N

物化性质

• 沸点：
  257.3±20.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  (R)-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one 在 吡啶 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 L-Selectride 、 copper(I) bromide 作用下， 反应 3.0h， 生成 (+)-Subcosine I
  参考文献：
  名称：

  Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates. Asymmetric syntheses of the quinolizidine alkaloids, (+)-myrtine, (-)-lasubine I, and (+)-subcosine I

  摘要：

  The first asymmetric syntheses of three quinolizidine alkaloids, (+)-myrtine, (-)-lasubine I, and (+)-subcosine I, were accomplished with a high degree of stereocontrol from readily available 4-methoxy-3-(triisopropylsilyl)pyridine in three, four, and five steps, respectively.

  DOI：

  10.1021/jo00048a003
• 作为产物：
  描述：

  (R)-tert-butyl 2-(2-(methoxy(methyl)amino)-2-oxoethyl)piperidine-1-carboxylate 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.5h， 生成 (R)-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one
  参考文献：
  名称：

  Amino Acid-Derived Enaminones:  A Study in Ring Formation Providing Valuable Asymmetric Synthons

  摘要：

  A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.

  DOI：

  10.1021/ja0609046

文献信息

• Amino Acid-Derived Enaminones:  A Study in Ring Formation Providing Valuable Asymmetric Synthons
  作者：Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/ja0609046

  日期：2006.7.1

  A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.
• Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates. Asymmetric syntheses of the quinolizidine alkaloids, (+)-myrtine, (-)-lasubine I, and (+)-subcosine I
  作者：Daniel L. Comins、Donald H. LaMunyon

  DOI：10.1021/jo00048a003

  日期：1992.10

  The first asymmetric syntheses of three quinolizidine alkaloids, (+)-myrtine, (-)-lasubine I, and (+)-subcosine I, were accomplished with a high degree of stereocontrol from readily available 4-methoxy-3-(triisopropylsilyl)pyridine in three, four, and five steps, respectively.