4-chloro-N-methyl-2,2-diphenylbutanamid | 37743-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-N-methyl-2,2-diphenylbutanamid
• 英文别名: 4-chloro-N-methyl-2,2-diphenylbutyramide；4-chloro-N-methyl-2,2-diphenylbutanamide
• CAS: 37743-08-1
• 化学式: C₁₇H₁₈ClNO
• 分子量: 287.789
• InChiKey: UOFMMQTWHKJOMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(4-氯苯基)-4-羟基哌啶 、 4-chloro-N-methyl-2,2-diphenylbutanamid 以 4-甲基-2-戊酮 为溶剂， 反应 12.0h， 以to provide 4-(p-chlorophenyl)-4-hydroxy-N-methyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride (0.8 g, 35%), mp 236-238° C.的产率得到4-(p-chlorophenyl)-4-hydroxy-N-methyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride
  参考文献：
  名称：

  Peripherally active anti-hyperalgesic opiates

  摘要：

  本文提供了用于治疗外周过度疼痛的组合物和使用该组合物的方法。该组合物含有一种或多种直接或间接与外周阿片受体相互作用的化合物的抗过度疼痛有效量，但是在局部或局部给药时不会引起明显的中枢神经系统效应。抗腹泻化合物4-(对氯苯基)-4-羟基-N-N-二甲基-α,α-二苯基-1-哌啶丁酰胺盐酸盐是该组合物和方法中首选的化合物。

  公开号：

  US05994372A1
• 作为产物：
  描述：

  N-(tetrahydro-3,3-diphenyl-2-furylidene)methylamine hydrobromide 在 盐酸 、 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 反应 1.0h， 生成 4-chloro-N-methyl-2,2-diphenylbutanamid
  参考文献：
  名称：

  A high-yield route to synthesize the P-glycoprotein radioligand [ C]N-desmethyl-loperamide and its parent radioligand [ C]loperamide

  摘要：

  N-Desmethyl-loperamide and loperamide were synthesized from a, a-diphenyl-c-butyrolactone and 4-(4-chlorophenyl)-4-hydroxypiperidine in five and four steps with 8% and 16% overall yield, respectively. The amide precursor was synthesized from 4-bromo-2,2-diphenylbutyronitrile and 4-(4-chlorophenyl)-4-hydroxypiperidine in 2 steps with 21-57% overall yield. [C-11] N-Desmethyl-loperamide and [C-11] loperamide were prepared from their corresponding amide precursor and N-desmethyl-loperamide with [C-11] CH3OTf through N-[C-11] methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 20-30% and 10-15% radiochemical yields, respectively, based on [C-11] CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/lmol specific activity at EOB. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.024

文献信息

• PERIPHERALLY ACTIVE ANTI-HYPERALGESIC OPIATES
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0852494A2

  公开（公告）日：1998-07-15
• US5994372A
  申请人：——

  公开号：US5994372A

  公开（公告）日：1999-11-30
• US6573282B1
  申请人：——

  公开号：US6573282B1

  公开（公告）日：2003-06-03
• [EN] PERIPHERALLY ACTIVE ANTI-HYPERALGESIC OPIATES<br/>[FR] OPIACES ANTI-HYPERALGESIQUES A ACTION PERIPHERIQUE
  申请人：——

  公开号：WO1997009973A2

  公开（公告）日：1997-03-20

  [EN] Compositions and methods using the compositions for treatment of peripheral hyperalgesia are provided. The compositions contain an anti-hyperalgesia effective amount of one or more compounds that directly or indirectly interact with peripheral opiate receptors, but that do not, upon topical or local administration, elicit substantial central nervous system effects. The anti-diarrheal compound 4-(p-chlorophenyl)-4-hydroxy-N-N-dimethyl- alpha , alpha -diphenyl-1-piperidinebutyramide hydrochloride is preferred for use in the compositions and methods.
  [FR] On décrit des compositions, et des procédés qui permettent de les utiliser, pour traiter l'hyperalgie périphérique. Ces compositions contiennent une quantité anti-hyperalgésique efficace d'un ou plusieurs composés qui interagissent, directement ou non, avec des récepteurs périphériques des opiacés mais n'entraînent pas d'effet marqué sur le système nerveux central en cas d'administration topique ou locale. Dans le cadre de l'utilisation de ces compositions et procédés, on retient de préférence un composé anti-diarrhéique, l'hydrochlorure de 4-(p-chlorophényl)-4-hydroxy-N-N-diméthyl- alpha , alpha -diphényl-1-pipéridinebutyramide.
• A high-yield route to synthesize the P-glycoprotein radioligand [ C]N-desmethyl-loperamide and its parent radioligand [ C]loperamide
  作者：Min Wang、Mingzhang Gao、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2013.08.024

  日期：2013.10

  N-Desmethyl-loperamide and loperamide were synthesized from a, a-diphenyl-c-butyrolactone and 4-(4-chlorophenyl)-4-hydroxypiperidine in five and four steps with 8% and 16% overall yield, respectively. The amide precursor was synthesized from 4-bromo-2,2-diphenylbutyronitrile and 4-(4-chlorophenyl)-4-hydroxypiperidine in 2 steps with 21-57% overall yield. [C-11] N-Desmethyl-loperamide and [C-11] loperamide were prepared from their corresponding amide precursor and N-desmethyl-loperamide with [C-11] CH3OTf through N-[C-11] methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 20-30% and 10-15% radiochemical yields, respectively, based on [C-11] CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/lmol specific activity at EOB. (C) 2013 Elsevier Ltd. All rights reserved.