2-Bromo-4-dipropylamino-cyclohexanone | 107431-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Bromo-4-dipropylamino-cyclohexanone
• 英文别名: 2-Bromo-4-(dipropylamino)cyclohexan-1-one
• CAS: 107431-11-8
• 化学式: C₁₂H₂₂BrNO
• 分子量: 276.217
• InChiKey: GNFOFAYZDCQALY-UHFFFAOYSA-N

物化性质

• 沸点：
  328.9±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-4-dipropylamino-cyclohexanone 在 四(三苯基膦)钯 哌啶 、 copper(l) iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.5h， 生成 dipropyl-[3-bromo-4-(trimethylsilylethynyl)-cyclohex-3-en-1-yl]amine
  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 diisopropyl amide 、 dibromotetrachloroethane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以66%的产率得到2-Bromo-4-dipropylamino-cyclohexanone
  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

文献信息

• Dialkylaminotetrahydrobenzothiazoles and oxazoles
  申请人：ELI LILLY AND COMPANY

  公开号：EP0207696A1

  公开（公告）日：1987-01-07

  ±-2-Amino-6-dialkylaminotetrahydrobenzothiazoles or oxazoles as receptor agonists.

  作为受体激动剂的±-2-氨基-6-二烷基氨基四氢苯并噻唑或噁唑。
• Fancy bioisosteres: synthesis and dopaminergic properties of the endiyne FAUC 88 as a novel non-aromatic D3 agonist
  作者：Carola Lenz、Christian Haubmann、Harald Hübner、Frank Boeckler、Peter Gmeiner

  DOI：10.1016/j.bmc.2004.09.044

  日期：2005.1

  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.