N¹²-acryloylcytisine | 27806-05-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: N¹²-acryloylcytisine
• 英文别名: (1R,5S)-3-Acryloyl-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one；(1R,9S)-11-prop-2-enoyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• CAS: 27806-05-9
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: WGUJNWLWQJNXIE-WDEREUQCSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  536.6±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-二巯基噻二唑 、 N¹²-acryloylcytisine 以 乙醇 、 苯 为溶剂， 以2.4 g的产率得到(1R,1'R,5S,5'S)-3,3'-(3,3'-((1,3,4-thiadiazole-2,5-diyl)bis(sulfanediyl))bis(propanoyl))bis(1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one)
  参考文献：
  名称：

  Reaction of 1,3,4-thiadiazol-2,5-dithiol with N-acryloyl-substituted derivatives of several alkaloids

  摘要：

  合成了潜在生物活性的2,5-bis-1,3,4-噻二唑衍生物，这些衍生物具有生物碱基团，采用1,3,4-噻二唑-2,5-二硫醇与N-丙烯酰基取代的生物碱衍生物（如小蛇麻、细辛素和D-伪麻黄碱）反应而得。

  DOI：

  10.1007/s10600-010-9493-9
• 作为产物：
  描述：

  丙烯酰氯 、 cytisine 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以47.2%的产率得到N¹²-acryloylcytisine
  参考文献：
  名称：

  (2-carbamoylethyl)bis(pentafluorophenyl)phosphine oxides: Synthesis and structure

  摘要：

  The interaction of a series of acrylic and cinnamic acid amides with bis(pentafluorophenyl)-phosphinic acid proceeds vigorously at room temperature without any catalyst in the presence of the organic solvents providing for a high fraction of the > P-OH tautomer of the phosphinic acid. The reactions have afforded (2-carbamoylethyl)bis(pentafluorophenyl)phosphine oxides in a high yield.

  DOI：

  10.1134/s1070363215090157

文献信息

• Synthesis and Crystal Structure of N-Acryloylcytisine and N-( -Morpholinopropionyl)cytisine
  作者：M. K. Ibraev、D. M. Turdybekov、S. D. Fazylov、K. M. Turdybekov、A. M. Gazaliev、T. S. Zhivotova

  DOI：10.1023/b:rujo.0000043720.17713.bd

  日期：2004.5

  N-acryloylcitisine and N-(beta morpholinopropionyl)cytisine were synthesized and spatial structures of compounds obtained were established by X-ray difraction analysis.
• (2-carbamoylethyl)bis(pentafluorophenyl)phosphine oxides: Synthesis and structure
  作者：E. I. Goryunov、I. B. Goryunova、K. A. Lysenko、N. G. Frolova、E. A. Latokhina、V. K. Brel

  DOI：10.1134/s1070363215090157

  日期：2015.9

  The interaction of a series of acrylic and cinnamic acid amides with bis(pentafluorophenyl)-phosphinic acid proceeds vigorously at room temperature without any catalyst in the presence of the organic solvents providing for a high fraction of the > P-OH tautomer of the phosphinic acid. The reactions have afforded (2-carbamoylethyl)bis(pentafluorophenyl)phosphine oxides in a high yield.
• Reaction of 1,3,4-thiadiazol-2,5-dithiol with N-acryloyl-substituted derivatives of several alkaloids
  作者：T. S. Zhivotova

  DOI：10.1007/s10600-010-9493-9

  日期：2009.11

  Potentially bioactive 2,5-bis derivatives of 1,3,4-thiadiazole with alkaloid moieties were synthesized by reaction of 1,3,4-thiadiazol-2,5-dithiol with N-acryloyl-substituted derivatives of the alkaloids anabasine, cytisine, and D-pseudoephedrine.

  合成了潜在生物活性的2,5-bis-1,3,4-噻二唑衍生物，这些衍生物具有生物碱基团，采用1,3,4-噻二唑-2,5-二硫醇与N-丙烯酰基取代的生物碱衍生物（如小蛇麻、细辛素和D-伪麻黄碱）反应而得。