Ethyl 2-diethylamino-3-cyclohexen-1-carboxylate | 129849-39-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 2-diethylamino-3-cyclohexen-1-carboxylate
• 英文别名: ethyl 2-(diethylamino)cyclohex-3-ene-1-carboxylate；1-Ethoxycarbonyl-2-diethylamino-cyclohex-3-en
• CAS: 129849-39-4
• 化学式: C₁₃H₂₃NO₂
• 分子量: 225.331
• InChiKey: MOHTWMPWFJZQIO-UHFFFAOYSA-N

物化性质

• 沸点：
  290.1±40.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-diethylamino-3-cyclohexen-1-carboxylate 在 溶剂黄146 、 potassium hydroxide 作用下， 生成 环己-1,3-二烯-1-羧酸
  参考文献：
  名称：

  Effect of the cross-linker on the general performance and temperature dependent behaviour of a molecularly imprinted polymer catalyst of a Diels–Alder reaction

  摘要：

  Here we present a series of molecularly imprinted polymers capable of catalysing the Diels-Alder reaction between benzyl 1,3-butadienylcarbamate (1) and N,N-dimethyl acrylamide (2). The polymer systems studied here demonstrated an unusual cross-linker and temperature dependent behaviour, namely that polymer catalysis of the Diels-Alder reaction was lower at elevated temperature, in contrast to the solution reaction. Furthermore, not only was the catalytic activity significantly influenced by the choice of cross-linker, but in a similar fashion also the extent of the temperature effect, indicating a close relationship between catalysis and the observed inhibition. Molecular dynamics simulations of both the polymer systems studied were used to provide insight into the molecular background of transition state stabilisation, and differences in properties of the systems based on different cross-linkers. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.06.006
• 作为产物：
  描述：

  1-(N,N-二乙氨基)-1,3-丁二烯 、 丙烯酸乙酯 以 甲苯 为溶剂， 反应 120.0h， 以84%的产率得到Ethyl 2-diethylamino-3-cyclohexen-1-carboxylate
  参考文献：
  名称：

  由鼠标嗅觉受体OR-I7碳链形状选择性†

  摘要：

  啮齿动物OR-I7是被脂族醛例如辛烷醛活化的嗅觉受体的例子。短于庚烷的正常链烷烃结合OR-1而不激活它，因此在体外起拮抗剂作用。我们报告了一系列醛，这些醛旨在探测对于太短的脂肪族配体链的结构要求，以致不能满足受体激活的最小约6.9Å长度的要求。使用异源细胞中表达的重组小鼠OR-I7进行的实验表明，在短醛拮抗剂的情况下，OR-I7更喜欢结合无分支的脂肪链，尽管允许碳3上有一个甲基。受体可以容纳出乎意料的大量碳（例如只要碳是构象约束环系统的一部分，则碳原子数为10）。与新拮抗剂对接的基于视紫红质的小鼠OR-I7同源模型表明，烷基链上的小烷基分支在空间上干扰结合位点上的疏水残基，但是当将碳原子绑回到紧凑的环系统中时，可以容纳分支碳原子像金刚烷基和双环[2.2.2]辛基系统。

  DOI：

  10.1039/c8ob00205c

文献信息

• IMPROVED AND EXPEDITIOUS MICROWAVE SYNTHESIS OF ETHYL 1,3-CYCLOHEXADDEN-1-CARBOXYLATE
  作者：Nicolas Tesson、Sandrine Deshayes

  DOI：10.1080/00304940009356744

  日期：2000.2

  Ethyl I ,3-cyclohexadien-1 -carboxylate (4) has often been used in Diels-Alder reactions with various dienophiles to build 1 ,Cdisubstituted bicyclo[2.2.2] octanes,' to synthesize aromatic esters (by cycloaddition to alkynes followed by aromatization of adducts)2 and to prepare molecules of biological interest such as tabtoxin (the exotoxin from Pseudomonus fabaci)3 and sirenin (a female sexual pheromone

  I,3-环己二烯-1-羧酸乙酯 (4) 经常用于与各种亲二烯体的 Diels-Alder 反应以构建 1 ,Cdi 取代的双环 [2.2.2] 辛烷，以合成芳香酯（通过环加成到炔烃，然后加合物的芳构化）2 并制备具有生物学意义的分子，例如 tabtoxin（来自蚕豆假单胞菌的外毒素）3 和 Sirenin（水生真菌 Allomyces 的雌性性信息素）！合成 4 的关键步骤最初由 Hunig 和 Kahanek 描述”并由 Grob 等人修改，b 是以良好的收率制备二烯胺 2，因为在蒸馏过程中发生广泛聚合。这种合成的主要缺点是反应时间长次（15 天），使用有毒溶剂（苯），多次蒸馏，重现性差，最佳产率为 30%。这篇文章描述了一种使用微波活化和干介质技术合成化合物 4 的改进程序，已知这些技术可以以提高的产率提供快速、清洁和经济的反应。
• HONEGGER E.; HEILBRONNER E.; HESS N.; MARTIN H. -D., CHEM. BER., 120,(1987) N 2, 187-193
  作者：HONEGGER E.、 HEILBRONNER E.、 HESS N.、 MARTIN H. -D.

  DOI：——

  日期：——
• Carbon chain shape selectivity by the mouse olfactory receptor OR-I7
  作者：Min Ting Liu、Jianghai Ho、Jason Karl Liu、Radhanath Purakait、Uriel N. Morzan、Lucky Ahmed、Victor S. Batista、Hiroaki Matsunami、Kevin Ryan

  DOI：10.1039/c8ob00205c

  日期：——

  cells show that in the context of short aldehyde antagonists, OR-I7 prefers binding aliphatic chains without branches, though a single methyl on carbon-3 is permitted. The receptor can accommodate a surprisingly large number of carbons (e.g. ten in adamantyl) as long as the carbons are part of a conformationally constrained ring system. A rhodopsin-based homology model of mouse OR-I7 docked with the new

  啮齿动物OR-I7是被脂族醛例如辛烷醛活化的嗅觉受体的例子。短于庚烷的正常链烷烃结合OR-1而不激活它，因此在体外起拮抗剂作用。我们报告了一系列醛，这些醛旨在探测对于太短的脂肪族配体链的结构要求，以致不能满足受体激活的最小约6.9Å长度的要求。使用异源细胞中表达的重组小鼠OR-I7进行的实验表明，在短醛拮抗剂的情况下，OR-I7更喜欢结合无分支的脂肪链，尽管允许碳3上有一个甲基。受体可以容纳出乎意料的大量碳（例如只要碳是构象约束环系统的一部分，则碳原子数为10）。与新拮抗剂对接的基于视紫红质的小鼠OR-I7同源模型表明，烷基链上的小烷基分支在空间上干扰结合位点上的疏水残基，但是当将碳原子绑回到紧凑的环系统中时，可以容纳分支碳原子像金刚烷基和双环[2.2.2]辛基系统。
• Effect of the cross-linker on the general performance and temperature dependent behaviour of a molecularly imprinted polymer catalyst of a Diels–Alder reaction
  作者：Henning Henschel、Nicole Kirsch、Jimmy Hedin-Dahlström、Michael J. Whitcombe、Susanne Wikman、Ian A. Nicholls

  DOI：10.1016/j.molcatb.2011.06.006

  日期：2011.11

  Here we present a series of molecularly imprinted polymers capable of catalysing the Diels-Alder reaction between benzyl 1,3-butadienylcarbamate (1) and N,N-dimethyl acrylamide (2). The polymer systems studied here demonstrated an unusual cross-linker and temperature dependent behaviour, namely that polymer catalysis of the Diels-Alder reaction was lower at elevated temperature, in contrast to the solution reaction. Furthermore, not only was the catalytic activity significantly influenced by the choice of cross-linker, but in a similar fashion also the extent of the temperature effect, indicating a close relationship between catalysis and the observed inhibition. Molecular dynamics simulations of both the polymer systems studied were used to provide insight into the molecular background of transition state stabilisation, and differences in properties of the systems based on different cross-linkers. (C) 2011 Elsevier B.V. All rights reserved.