N-(tetrahydro-3,3-diphenyl-2-furylidene)methylamine hydrobromide | 37743-06-9

• 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: N-(tetrahydro-3,3-diphenyl-2-furylidene)methylamine hydrobromide
• 英文别名: N-methyl-3,3-diphenyloxolan-2-imine;hydrobromide
• CAS: 37743-06-9
• 化学式: BrH*C₁₇H₁₇NO
• 分子量: 332.24
• InChiKey: VEIYFKGJETYOLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  21.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(tetrahydro-3,3-diphenyl-2-furylidene)methylamine hydrobromide 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 N-methyl-3,3-diphenyloxolan-2-imine
  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
• 作为产物：
  描述：

  双苯溴丁酸 在 氯化亚砜 、 sodium carbonate 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 N-(tetrahydro-3,3-diphenyl-2-furylidene)methylamine hydrobromide
  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：Regents of the University of California

  公开号：US05994372A1

  公开（公告）日：1999-11-30

  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-piper idinebutyramide hydrochloride is preferred for use in the compositions and methods.

  本发明提供了用于治疗外周高痛觉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化合物的抗高痛觉有效量，这些化合物直接或间接与外周阿片受体相互作用，但在局部或局部给药时不会引起重大的中枢神经系统效应。优选用于该组合物和方法的是抗腹泻化合物4-（对氯苯基）-4-羟基-N-二甲基-α，α-二苯基-1-哌啶丁酰胺盐酸盐。
• 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.