(+/-)-N-Benzylhygrine | 135108-27-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (+/-)-N-Benzylhygrine
• 英文别名: 1-benzyl-2-acetonylpyrrolidine；1-(1-benzylpyrrolidin-2-yl)propan-2-one
• CAS: 135108-27-9
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: QLKGOCRHCASCKI-UHFFFAOYSA-N

物化性质

• 沸点：
  315.1±17.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-benzyl-2-pyrrolidinethione 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 双氧水 、 二(3-甲基丁烷-2-基)硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 (+/-)-N-Benzylhygrine
  参考文献：
  名称：

  Takahata, Hiroki; Takahashi, Koichi; Wang, Eng-Chi, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1211 - 1214

  摘要：

  DOI：

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。
• Oxidative methods for promoting iminium cation cyclization reactions
  作者：Xiaoming Zhang、Young Shik Jung、Patrick S. Mariano、Marye Anne Fox、Polly S. Martin、Jon Merkert

  DOI：10.1016/s0040-4039(00)73962-1

  日期：1993.8

  A new methodology for promoting iminium cation cyclization reactions, involving oxidation of α-silylamines, is presented.

  提出了一种促进亚胺阳离子环化反应的新方法，该方法涉及α-甲硅烷基胺的氧化。
• Amine-flavin electron transfer photochemistry. Potential models for monoamine oxidase catalysis and inhibition
  作者：Jong Man Kim、In Seop Cho、Patrick S. Mariano

  DOI：10.1021/jo00016a026

  日期：1991.8

  The photoreactions of 3-methyllumiflavin (3MLF) and a variety of amines have been explored. These studies have demonstrated that 3MLF undergoes efficient photoreactions with alpha-silyl tertiary benzylamines to generate 4a-adducts by pathways involving sequential SET and desilylation followed by radical coupling. These adducts are unstable substances that react rapidly with nucleophiles (e.g., MeOH, H2O, and NaBH4) and oxygen. They are also photolabile, providing the corresponding 4a-benzyldihydroflavin upon irradiation. Non-silicon-containing primary and secondary amines also participate in SET-promoted photoreactions with 3MLF. The amine cation radicals formed in these processes undergo further transformations to produce radical intermediates by either alpha-CH or NH deprotonation pathways. The potential relevance of these findings to the area of monoamine oxidase chemistry is considered.
• Jeon, Yoon T.; Lee, Chao-Pin; Mariano, Patrick S., Journal of the American Chemical Society, 1991, vol. 113, # 23, p. 8847 - 8863
  作者：Jeon, Yoon T.、Lee, Chao-Pin、Mariano, Patrick S.

  DOI：——

  日期：——
• TAKAHATA, HIROKI;TAKAHASHI, KOICHI;WANG, ENG-CHI;YAMAZAKI, TAKAO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 1211-1214
  作者：TAKAHATA, HIROKI、TAKAHASHI, KOICHI、WANG, ENG-CHI、YAMAZAKI, TAKAO

  DOI：——

  日期：——