(1S,5S,8R)-8-N-acetylamino-2,4,4,8-tetramethyl-3-azabicyclo<3.3.1>non-2-ene | 93302-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1S,5S,8R)-8-N-acetylamino-2,4,4,8-tetramethyl-3-azabicyclo<3.3.1>non-2-ene
• 英文别名: N-((1S,5S,6S)-2,2,4,6-tetramethyl-3-azabicyclo[3.3.1]non-3-en-6-yl)acetamide；N-((1s,5s,6s)-2,2,4,6-tetramethyl-3-azabicyclo[3.3.1]non-3-en-6-yl)acetamide；N-[(1S,5S,6S)-2,2,4,6-tetramethyl-3-azabicyclo[3.3.1]non-3-en-6-yl]acetamide
• CAS: 93302-52-4
• 化学式: C₁₄H₂₄N₂O
• 分子量: 236.357
• InChiKey: AKRBICRIVVVNDO-SCRDCRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,5S,8R)-8-N-acetylamino-2,4,4,8-tetramethyl-3-azabicyclo<3.3.1>non-2-ene 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以97%的产率得到rel-N-((1S,4R,5R,6S)-2,2,4,6-tetramethyl-3-azabicyclo[3.3.1]nonan-6-yl)acetamide
  参考文献：
  名称：

  从桥接的Ritter反应获得的生物碱样3-氮杂双环[3.3.1] non-3-ene库

  摘要：

  使用与（-）-β-pine烯的桥连Ritter反应和随后的支架衍生化反应，合成了一个小型多样的新型生物碱样化合物。通过改变反应中使用的腈来实现结构多样性，从而了解了腈对反应结果的影响。已经确定，更多的亲核腈产生更高的产率。立体因素还决定了所产生支架类型的选择性，其中较大的基团主要产生烯烃产物。X射线晶体学以及尝试衍生自桥式Ritter反应的亚胺的尝试，突出了亚氨基氮由于根本不被相邻取代基拥挤而根本不发生或以立体定向方式发生反应的方式。由于化合物包含3-氮杂双环[3.3。

  DOI：

  10.1016/j.tet.2016.11.057
• 作为产物：
  描述：

  beta-pinene 、 乙腈 在 硫酸 、 水 作用下， 以 苯 为溶剂， 反应 24.5h， 以64%的产率得到(1S,5S,8R)-8-N-acetylamino-2,4,4,8-tetramethyl-3-azabicyclo<3.3.1>non-2-ene
  参考文献：
  名称：

  Formation of 3-azabicyclo[3.3.1]non-3-enes: imino amides vs. imino alkenes

  摘要：

  An effective method for synthesising alkaloidlike compounds containing the 3-azabicyclo[3.3.1]non-3-ene core structure was successfully carried out in a stereo-selective manner via the bridged-Ritter reactions. Important optically active 6-alkyl(aryl)amido-4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]non-3-enes (imino amides) and 4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]nona-3,6-dienes (imino alkenes) were obtained in one step from (-)-beta-pinene and the respective nitriles in the presence of concentrated H2SO4. The relative compositions of these products were controlled by varying the reaction conditions. Kinetic studies were conducted to enable a mechanistic understanding of the reaction pathways.

  DOI：

  10.1007/s00706-014-1185-x

文献信息

• Koval'skaya, S.S.; Kozlov, N.G.; Kalechits, G.V., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 4.1, p. 649 - 652
  作者：Koval'skaya, S.S.、Kozlov, N.G.、Kalechits, G.V.

  DOI：——

  日期：——
• An alkaloid-like 3-azabicyclo[3.3.1]non-3-ene library obtained from the bridged Ritter reaction
  作者：Steven G. Williams、Mohan Bhadbhade、Roger Bishop、Alison T. Ung

  DOI：10.1016/j.tet.2016.11.057

  日期：2017.1

  diverse library of novel alkaloid-like compounds was synthesised using the bridged Ritter reaction with (−)-β-pinene and subsequent scaffold derivatisation. Structural diversity was achieved by varying the nitrile used in the reaction and thus provided an understanding of the influence nitriles have on the reaction outcome; it was determined that more nucleophilic nitriles, gave higher yields. Steric

  使用与（-）-β-pine烯的桥连Ritter反应和随后的支架衍生化反应，合成了一个小型多样的新型生物碱样化合物。通过改变反应中使用的腈来实现结构多样性，从而了解了腈对反应结果的影响。已经确定，更多的亲核腈产生更高的产率。立体因素还决定了所产生支架类型的选择性，其中较大的基团主要产生烯烃产物。X射线晶体学以及尝试衍生自桥式Ritter反应的亚胺的尝试，突出了亚氨基氮由于根本不被相邻取代基拥挤而根本不发生或以立体定向方式发生反应的方式。由于化合物包含3-氮杂双环[3.3。
• Formation of 3-azabicyclo[3.3.1]non-3-enes: imino amides vs. imino alkenes
  作者：Alison T. Ung、Steven G. Williams、Alexander Angeloski、Jason Ashmore、Unnikrishnan Kuzhiumparambil、Mohan Bhadbhade、Roger Bishop

  DOI：10.1007/s00706-014-1185-x

  日期：2014.6

  An effective method for synthesising alkaloidlike compounds containing the 3-azabicyclo[3.3.1]non-3-ene core structure was successfully carried out in a stereo-selective manner via the bridged-Ritter reactions. Important optically active 6-alkyl(aryl)amido-4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]non-3-enes (imino amides) and 4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]nona-3,6-dienes (imino alkenes) were obtained in one step from (-)-beta-pinene and the respective nitriles in the presence of concentrated H2SO4. The relative compositions of these products were controlled by varying the reaction conditions. Kinetic studies were conducted to enable a mechanistic understanding of the reaction pathways.