(S)-2-benzyl-2,3-dihydropyridin-4(1H)-one | 244183-01-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-benzyl-2,3-dihydropyridin-4(1H)-one
• 英文别名: (2S)-2-benzyl-2,3-dihydro-4-pyridone；(2S)-2-benzyl-2,3-dihydro-1H-pyridin-4-one
• CAS: 244183-01-5
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: XQSGIPKFGJUAGV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-benzyl-2,3-dihydropyridin-4(1H)-one 在 lithium aluminium tetrahydride 、 正丁基锂 、 cerium(III) chloride 、 氢溴酸 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,5S,9S)-(+)-5,9-dimethyl-2-methyl-6,7-benzomorphan
  参考文献：
  名称：

  对映体N-酰基二氢吡啶酮类化合物的合成中间体：苯并吗啡啉的不对称合成。

  摘要：

  使用对映体纯的2,3-二氢-4-吡啶酮作为手性结构单元，已经完成了几种苯并吗啡酮衍生物的简明不对称合成。

  DOI：

  10.1021/ol990738p
• 作为产物：
  描述：

  (+)-trans-2-(α-cumyl)cyclohexyl chloroformate 在 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (S)-2-benzyl-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  对映体N-酰基二氢吡啶酮类化合物的合成中间体：苯并吗啡啉的不对称合成。

  摘要：

  使用对映体纯的2,3-二氢-4-吡啶酮作为手性结构单元，已经完成了几种苯并吗啡酮衍生物的简明不对称合成。

  DOI：

  10.1021/ol990738p

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).
• 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 <i>N</i>-Acyldihydropyridones as Synthetic Intermediates:  Asymmetric Synthesis of Benzomorphans
  作者：Daniel L. Comins、Yue-mei Zhang、Sajan P. Joseph

  DOI：10.1021/ol990738p

  日期：1999.8.1

  [formula: see text] Concise asymmetric syntheses of several benzomorphan derivatives have been accomplished using enantiopure 2,3-dihydro-4-pyridones as chiral building blocks.

  使用对映体纯的2,3-二氢-4-吡啶酮作为手性结构单元，已经完成了几种苯并吗啡酮衍生物的简明不对称合成。