4-phenyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one | 905717-32-0

• 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: 4-phenyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one
• 英文别名: 4-phenyl-1,6,7,8,9,9a-hexahydro-2H-quinolizin-2-one；4-Phenyl-1,6,7,8,9,9a-hexahydroquinolizin-2-one；4-phenyl-1,6,7,8,9,9a-hexahydroquinolizin-2-one
• CAS: 905717-32-0
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: DIWZFDLGSDGGTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-phenyl-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one 在 碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到3-Iodo-4-phenyl-1,6,7,8,9,9a-hexahydroquinolizin-2-one
  参考文献：
  名称：

  Microwave-assisted Suzuki–Miyaura couplings on α-iodoenaminones

  摘要：

  A systematic study of alpha-iodination and subsequent Suzuki-Miyaura couplings between non-attenuated enaminones and a wide range of aromatic boronic acids is reported. The microwave-assisted variant of this transformation furnished the alpha-arylenaminones in significantly shorter reaction times and slightly improved yields as compared to conventional heating. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.078
• 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 4-phenyl-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

• α-C–H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines
  作者：Jae Hyun Kim、Anirudra Paul、Ion Ghiviriga、Daniel Seidel

  DOI：10.1021/acs.orglett.0c04024

  日期：2021.2.5

  lithium amides by oxidation with simple ketone oxidants, are readily alkylated with a range of enolates to provide mono- and polycyclic β-aminoketones in a single operation, including the natural product (±)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations, which are promoted by BF3 etherate. β-Aminoesters derived from ester enolates can be converted to the corresponding

  可烯醇化的环状亚胺是通过用简单的酮氧化剂氧化从相应的氨基锂原位获得的，很容易用一系列烯醇化物烷基化，在一次操作中提供单环和多环 β-氨基酮，包括天然产物 (±)-肉豆蔻碱。腈阴离子也在这些转化中充当有效的亲核试剂，BF 3醚化物促进了这些转化。源自酯烯醇化物的β-氨基酯可以转化为相应的β-内酰胺。
• 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.
• Microwave-assisted Suzuki–Miyaura couplings on α-iodoenaminones
  作者：Xin Wang、Brandon J. Turunen、Matthew W. Leighty、Gunda I. Georg

  DOI：10.1016/j.tetlet.2007.10.078

  日期：2007.12

  A systematic study of alpha-iodination and subsequent Suzuki-Miyaura couplings between non-attenuated enaminones and a wide range of aromatic boronic acids is reported. The microwave-assisted variant of this transformation furnished the alpha-arylenaminones in significantly shorter reaction times and slightly improved yields as compared to conventional heating. (C) 2007 Elsevier Ltd. All rights reserved.