2-(1-benzylpyrrolidin-2-yl)-1-phenylethanone | 1144516-25-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-benzylpyrrolidin-2-yl)-1-phenylethanone
• CAS: 1144516-25-5
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: JYGPAMJQZXHGGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  403.7±18.0 °C(predicted)
• 密度：
  1.095±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-2-(1-benzylpyrrolidin-2-ylidene)-1-phenylethanone 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以89%的产率得到2-(1-benzylpyrrolidin-2-yl)-1-phenylethanone
  参考文献：
  名称：

  Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

  摘要：

  The conditions of the Eschenmoser coupling reaction were studied. The formation of the alpha-thioiminium ion was achieved faster in the presence of an additive (Nal) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.081

文献信息

• Biomimetic Approach toward the Total Synthesis of <i>rac</i>-2-(Acylmethylene)pyrrolidine Alkaloids
  作者：Yu-Chiao Shih、Pei-Hua Tsai、Chia-Chun Hsu、Chih-Wei Chang、Yuandong Jhong、Yun-Chung Chen、Tun-Cheng Chien

  DOI：10.1021/acs.joc.5b00836

  日期：2015.7.2

  intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.

  2-（Acylmethylene）吡咯烷衍生物通过从各种甲基酮和1-烷基-1- pyrroliniums，生成分子间decarbonylative曼尼希反应合成原位由1- alkylprolines。该方法模拟了生物合成途径，并提供了直接接触一系列2-（酰基亚甲基）吡咯烷生物碱的方法，包括hy，N-甲基ruspolinone，dehydrodarlinine和ruspolinone。
• Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C–H nucleophiles with low catalyst loading
  作者：Jing Guo、Ying Xie、Qiao-Lei Wu、Wen-Tian Zeng、Albert S. C. Chan、Jiang Weng、Gui Lu

  DOI：10.1039/c8ra02340a

  日期：——

  An aerobic decarboxylative cross-coupling of α-amino acids with diverse C–H nucleophiles has been realized using Cu2(OH)2CO3 (1 mol%) as the catalyst under air. This protocol enables highly efficient formation of various C(sp3)–C(sp3), C(sp3)–C(sp2) and C(sp3)–C(sp) bonds under simple conditions without the use of any ligand or extra oxidant, providing a practical approach to numerous nitrogen-containing

  使用Cu 2 (OH) 2 CO 3 (1 mol%)作为催化剂在空气下实现了α-氨基酸与多种C-H亲核试剂的需氧脱羧交叉偶联。该协议能够在简单的条件下高效形成各种 C(sp 3 )–C(sp 3 )、C(sp 3 )–C(sp 2 ) 和 C(sp 3 )–C(sp) 键，而无需使用任何配体或额外的氧化剂，为许多含氮化合物提供了一种实用的方法，产率从良好到极好。克级实验和 Rad51 抑制剂的三步合成也证明了效率和实用性。