2-bromo-4-(dipropylamino)cyclohex-1-en-1-yl trifluoromethanesulfonate | 834918-93-3

• 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: 2-bromo-4-(dipropylamino)cyclohex-1-en-1-yl trifluoromethanesulfonate
• CAS: 834918-93-3
• 化学式: C₁₃H₂₁BrF₃NO₃S
• 分子量: 408.28
• InChiKey: ISBJIQFTLOXMCU-UHFFFAOYSA-N

物化性质

• 沸点：
  388.5±42.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-bromo-4-(dipropylamino)cyclohex-1-en-1-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 tris(dibenzylideneacetone)dipalladium (0) 哌啶 、 1,1'-双(二苯基膦)二茂铁 、 copper(l) iodide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 13.0h， 生成 5-(Dipropylamino)-2-ethynylcyclohex-1-ene-1-carbonitrile
  参考文献：
  名称：

  Fancy bioisosteres: synthesis and dopaminergic properties of the endiyne FAUC 88 as a novel non-aromatic D3 agonist

  摘要：

  Enlargement of the pi-electronic system of the non-aromatic D3 agonist FAUC 73 led to dopaminergic endiynes of type 1 being synthesized via the bromovinyl triflate 7a as a key intermediate when palladium catalyzed coupling reactions were exploited for the introduction of the (aza)alkyne substituents. As the first neuroreceptor active endiyne, FAUC 88 (1c) displayed high and selective dopamine D3 receptor affinity (K-i high = 3.2 nM) and substantial ligand efficacy (72%, EC50 = 2.5 nM). Similarities between molecular electrostatic potentials induced by the catechol subunit of the genuine neurotransmitter and those of its non-aromatic endiyne bioisostere are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.044
• 作为产物：
  描述：

  4-di-n-propylaminocyclohexanone 在 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.5h， 生成 2-bromo-4-(dipropylamino)cyclohex-1-en-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Fancy bioisosteres: synthesis and dopaminergic properties of the endiyne FAUC 88 as a novel non-aromatic D3 agonist

  摘要：

  Enlargement of the pi-electronic system of the non-aromatic D3 agonist FAUC 73 led to dopaminergic endiynes of type 1 being synthesized via the bromovinyl triflate 7a as a key intermediate when palladium catalyzed coupling reactions were exploited for the introduction of the (aza)alkyne substituents. As the first neuroreceptor active endiyne, FAUC 88 (1c) displayed high and selective dopamine D3 receptor affinity (K-i high = 3.2 nM) and substantial ligand efficacy (72%, EC50 = 2.5 nM). Similarities between molecular electrostatic potentials induced by the catechol subunit of the genuine neurotransmitter and those of its non-aromatic endiyne bioisostere are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.044