4-(dimethylamino)-1-(4-fluorophenyl)butan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(dimethylamino)-1-(4-fluorophenyl)butan-1-one
• 英文别名: 4-Dimethylamino-1-(4-fluoro-phenyl)-butan-1-one
• 化学式: C₁₂H₁₆FNO
• 分子量: 209.264
• InChiKey: XFRVODFWEKRMLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)-1-(4-fluorophenyl)butan-1-one 在 sodium tetrahydroborate 、 正丁基锂 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 4-(4-二甲胺基-1-对氟苯基-1-羟基丁基)-3-(羟甲基)苯腈
  参考文献：
  名称：

  一种西酞普兰中间体的合成方法

  摘要：

  本发明提供了一种西酞普兰中间体4‑(4‑(二甲胺基)‑1‑(4‑氟苯基)‑1‑羟基丁基)‑3‑(羟甲基)苯甲腈的制备方法。本发明所述的方法具有原料廉价易得，反应步骤短，收率高，后处理简单、易操作等优点，降低了成本，具有一定的技术优势，适合大规模工业生产。

  公开号：

  CN111533662B
• 作为产物：
  描述：

  2-(3-氯丙基)-2-(4-氟苯基)-1,3-二氧戊烷 在 盐酸 、 甲酸 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 4-(dimethylamino)-1-(4-fluorophenyl)butan-1-one
  参考文献：
  名称：

  Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT2- versus 5-HT1C-selective antagonist

  摘要：

  DOM [i.e., 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane] is a 5-HT1C/2 serotonin agonist that exerts stimulus control of behavior in animals. In order to determine if the discriminative stimulus effect of DOM is 5-HT1C- or 5-HT2-mediated, it would be informative to conduct tests of stimulus antagonism with a 5-HT1C- or 5-HT2-selective antagonist. To date, no such agents exist. Although the neuroleptic agent spiperone binds at D2 dopamine receptors and 5-HT1A serotonin receptors, (a) it displays about a 1000-fold selectivity for 5-HT2 versus 5-HT1C sites and (b) it has been used as a ''5-HT2-selective'' antagonist. Because spiperone is a behaviorally disruptive agent, it is not suitable for use in drug-discrimination studies. Using the spiperone molecule as a starting point, a limited structure-affinity investigation was conducted in order to identify a suitable antagonist with high affinity and selectivity for 5-HT2 receptors, and yet an antagonist that might lack the disruptive actions of spiperone. Various modifications of the spiperone molecule were examined, but most resulted in decreased 5-HT2 affinity or in loss of selectivity. One compound, 8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one(26), was shown to bind at 5-HT2 sites with high affinity (K(i) = 2 nM) and >2,000-fold selectivity versus 5-HT1C sites. In tests of stimulus antagonism using rats trained to discriminate 1 mg/kg of DOM from saline vehicle, 26 behaved as a potent antagonist (ED50 = 0.003 mg/kg) and lacked the disruptive effects associated with spiperone. As such, (a) it would appear that the DOM stimulus is primarily a 5-HT2-mediated, and not 5-HT1C-mediated, phenomenon, and (b) compound 26 may find application in other pharmacologic investigations where spiperone may not be a suitable antagonist.

  DOI：

  10.1021/jm00069a010

文献信息

• Method for the preparation of citalopram
  申请人：H. Lundbeck A/S

  公开号：US20020040153A1

  公开（公告）日：2002-04-04

  A method for the preparation of citalopram comprising reductive hydrolysis of a compound of Formula (IV) 1 wherein R is a N,N-disubstituted amid group or an optionally substituted 4,5-dihydro-1,3-oxazol-2-yl group, and conversion of the resulting 5-formyl compound to citalopram.

  一种制备西酞普兰的方法，包括对式（IV）的化合物进行还原水解，其中R是N,N-二取代酰胺基团或可选择取代的4,5-二氢-1,3-噁唑-2-基基团，并将所得的5-甲醛化合物转化为西酞普兰。
• METHOD FOR THE PREPARATION OF CITALOPRAM
  申请人：H. LUNDBECK A/S

  公开号：EP1173431B1

  公开（公告）日：2003-04-16
• US5534629A
  申请人：——

  公开号：US5534629A

  公开（公告）日：1996-07-09
• US6849749B2
  申请人：——

  公开号：US6849749B2

  公开（公告）日：2005-02-01
• US7030252B2
  申请人：——

  公开号：US7030252B2

  公开（公告）日：2006-04-18