(S)-6-(4-methoxyphenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one | 1242597-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-6-(4-methoxyphenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one
• 英文别名: (8aS)-6-(4-methoxyphenyl)-2,3,8,8a-tetrahydro-1H-indolizin-7-one
• CAS: 1242597-66-5
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: MTEFHBANSTWWSG-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-6-(4-methoxyphenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 4.75h， 以90%的产率得到1-aza-3-(4-methoxyphenyl)bicyclo<4,3,0>nonan-4-one
  参考文献：
  名称：

  Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine

  摘要：

  This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C-H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24-26% overall yields.

  DOI：

  10.1021/jo101051w
• 作为产物：
  描述：

  (S)-2,3,8,8a-tetrahydroindolizin-7(1H)-one 、 (4-甲氧基苯基)三氟硼酸钾 在 copper diacetate 、 palladium diacetate 、 potassium carbonate 作用下， 以 溶剂黄146 、 二甲基亚砜 、 叔丁醇 为溶剂， 生成 (S)-6-(4-methoxyphenyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one
  参考文献：
  名称：

  Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism

  摘要：

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction 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 die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).

  DOI：

  10.1021/jo100907u

文献信息

• Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism
  作者：Micah J. Niphakis、Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/jo100907u

  日期：2010.10.15

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction 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 die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).
• Total Syntheses of Arylindolizidine Alkaloids (+)-Ipalbidine and (+)-Antofine
  作者：Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/jo101051w

  日期：2010.9.3

  This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C-H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24-26% overall yields.