trifluoromethanesulfonic acid 4-dipropylaminocyclohex-1-enyl ester | 262427-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trifluoromethanesulfonic acid 4-dipropylaminocyclohex-1-enyl ester
• 英文别名: [4-(Dipropylamino)cyclohexen-1-yl] trifluoromethanesulfonate
• CAS: 262427-72-5
• 化学式: C₁₃H₂₂F₃NO₃S
• 分子量: 329.384
• InChiKey: IRXCZORTECOXAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  358.9±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 4-dipropylaminocyclohex-1-enyl ester 在 copper(l) iodide 、 四(三苯基膦)钯 、 二甲基十二/十四烷基叔胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 FAUC 73
  参考文献：
  名称：

  Conjugated Enynes as Nonaromatic Catechol Bioisosteres:  Synthesis, Binding Experiments, and Computational Studies of Novel Dopamine Receptor Agonists Recognizing Preferentially the D₃ Subtype

  摘要：

  To evaluate nonaromatic catechol bioisosteres, the conformationally restrained enynes 1 and enediynes 2 were synthesized via palladium-catalyzed coupling as the key reaction step. Subsequent receptor binding studies at the dopamine receptor subtypes D-1, D-2 long, D-2 short, D-3, and D-4 showed highly interesting binding profiles for the enynes la and 1b when compared to dopamine. At the guanine nucleotide-sensitive high-affinity binding site of the Da receptor, the target compound 1b (K-i = 5.2 nM) was 10-fold more potent than dopamine but less potent at the D-2 and D-4 subtypes. In contrast to dopamine the agonists la and Ib showed strong selectivity for the receptors of the D-2 family (D-2-D-4) As far as We know, this study represents the first report on nonaromatic dopamine agonists. Comparison of molecular electrostatic potentials, derived from semiempirical molecular orbital calculations, and lipophilicity maps was performed.

  DOI：

  10.1021/jm991098z
• 作为产物：
  描述：

  三氟甲磺酸酐 、 4-di-n-propylaminocyclohexanone 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.5h， 以43%的产率得到trifluoromethanesulfonic acid 4-dipropylaminocyclohex-1-enyl ester
  参考文献：
  名称：

  Conjugated Enynes as Nonaromatic Catechol Bioisosteres:  Synthesis, Binding Experiments, and Computational Studies of Novel Dopamine Receptor Agonists Recognizing Preferentially the D₃ Subtype

  摘要：

  To evaluate nonaromatic catechol bioisosteres, the conformationally restrained enynes 1 and enediynes 2 were synthesized via palladium-catalyzed coupling as the key reaction step. Subsequent receptor binding studies at the dopamine receptor subtypes D-1, D-2 long, D-2 short, D-3, and D-4 showed highly interesting binding profiles for the enynes la and 1b when compared to dopamine. At the guanine nucleotide-sensitive high-affinity binding site of the Da receptor, the target compound 1b (K-i = 5.2 nM) was 10-fold more potent than dopamine but less potent at the D-2 and D-4 subtypes. In contrast to dopamine the agonists la and Ib showed strong selectivity for the receptors of the D-2 family (D-2-D-4) As far as We know, this study represents the first report on nonaromatic dopamine agonists. Comparison of molecular electrostatic potentials, derived from semiempirical molecular orbital calculations, and lipophilicity maps was performed.

  DOI：

  10.1021/jm991098z

文献信息

• Analogues of FAUC 73 revealing new insights into the structural requirements of nonaromatic dopamine D3 receptor agonists
  作者：Carola Lenz、Frank Boeckler、Harald Hübner、Peter Gmeiner

  DOI：10.1016/j.bmc.2003.10.011

  日期：2004.1

  Employing the nonaromatic D3 agonist FAUC 73 as a lead compound, the dopaminergic enynes 1a,b and the diene 2 (FAUC 206) were synthesized via palladium-catalyzed cross-coupling. FAUC 206 showed remarkable D3 affinity and enhanced selectivity over D4 when compared to the lead compound. To learn more about the bioactive structure of the diene moiety, computational studies including DFT-based conformational analysis and calculations of the magnetic shielding properties were performed. The electrostatic properties of the pharmacophoric pi-systems were visualized by diagnostic MEP maps. (C) 2003 Elsevier Ltd. All rights reserved.
• Conjugated Enynes as Nonaromatic Catechol Bioisosteres:  Synthesis, Binding Experiments, and Computational Studies of Novel Dopamine Receptor Agonists Recognizing Preferentially the D₃ Subtype
  作者：Harald Hübner、Christian Haubmann、Wolfgang Utz、Peter Gmeiner

  DOI：10.1021/jm991098z

  日期：2000.2.1

  To evaluate nonaromatic catechol bioisosteres, the conformationally restrained enynes 1 and enediynes 2 were synthesized via palladium-catalyzed coupling as the key reaction step. Subsequent receptor binding studies at the dopamine receptor subtypes D-1, D-2 long, D-2 short, D-3, and D-4 showed highly interesting binding profiles for the enynes la and 1b when compared to dopamine. At the guanine nucleotide-sensitive high-affinity binding site of the Da receptor, the target compound 1b (K-i = 5.2 nM) was 10-fold more potent than dopamine but less potent at the D-2 and D-4 subtypes. In contrast to dopamine the agonists la and Ib showed strong selectivity for the receptors of the D-2 family (D-2-D-4) As far as We know, this study represents the first report on nonaromatic dopamine agonists. Comparison of molecular electrostatic potentials, derived from semiempirical molecular orbital calculations, and lipophilicity maps was performed.