(4-dibromomethylenecyclohexyl)dipropylamine | 262427-73-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-dibromomethylenecyclohexyl)dipropylamine
• 英文别名: 4-(dibromomethylidene)-N,N-dipropylcyclohexan-1-amine
• CAS: 262427-73-6
• 化学式: C₁₃H₂₃Br₂N
• 分子量: 353.14
• InChiKey: CPACGKCLWYDXPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-dibromomethylenecyclohexyl)dipropylamine 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 [4-(1-Ethynyl-prop-2-ynylidene)-cyclohexyl]-dipropyl-amine
  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：

  四溴化碳 、 4-di-n-propylaminocyclohexanone 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 4.0h， 以84%的产率得到(4-dibromomethylenecyclohexyl)dipropylamine
  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

• 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.