8-[4,4-bis(p-fluorophenyl)-4-hydroxybutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one | 817642-33-4

• 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: 8-[4,4-bis(p-fluorophenyl)-4-hydroxybutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
• 英文别名: 8-[4,4-Bis(4-fluorophenyl)-4-hydroxybutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
• CAS: 817642-33-4
• 化学式: C₂₉H₃₁F₂N₃O₂
• 分子量: 491.581
• InChiKey: CWLYIHBSQATXGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C(Solv: ethanol (64-17-5))
• 沸点：
  709.8±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  55.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-[4,4-bis(p-fluorophenyl)-4-hydroxybutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、150.0 kPa 条件下， 反应 76.0h， 生成 帕罗西汀 杂质C
  参考文献：
  名称：

  Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines

  摘要：

  Pharmacologically active 4,4-diarylbutylamines like Fluspirilene and 4-amino-1,1-diarylbutan-1-ols like Difenidol were prepared in high yields via rhodium catalysed hydroaminomethylation of 1,1-diaryl-allylalcohols. Conversion of these olefins with carbon monoxide, hydrogen and secondary amines proceeds with complete regioselectivity. This group can easily be removed under acidic and hydrogenating conditions, enabling the transformation of 4-amino-1,1-diarylbutan-1-ols to 4,4-diarylbutylamines in high yields. Thus Fluspirilene was synthesised in 88% yield in four steps starting from commercially available materials. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.058
• 作为产物：
  描述：

  4,4'-二氟二苯甲酮 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 120.0 ℃ 、5.0 MPa 条件下， 反应 65.0h， 生成 8-[4,4-bis(p-fluorophenyl)-4-hydroxybutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
  参考文献：
  名称：

  Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines

  摘要：

  Pharmacologically active 4,4-diarylbutylamines like Fluspirilene and 4-amino-1,1-diarylbutan-1-ols like Difenidol were prepared in high yields via rhodium catalysed hydroaminomethylation of 1,1-diaryl-allylalcohols. Conversion of these olefins with carbon monoxide, hydrogen and secondary amines proceeds with complete regioselectivity. This group can easily be removed under acidic and hydrogenating conditions, enabling the transformation of 4-amino-1,1-diarylbutan-1-ols to 4,4-diarylbutylamines in high yields. Thus Fluspirilene was synthesised in 88% yield in four steps starting from commercially available materials. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.058

文献信息

• Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines
  作者：Andreas Schmidt、Mauro Marchetti、Peter Eilbracht

  DOI：10.1016/j.tet.2004.09.058

  日期：2004.12

  Pharmacologically active 4,4-diarylbutylamines like Fluspirilene and 4-amino-1,1-diarylbutan-1-ols like Difenidol were prepared in high yields via rhodium catalysed hydroaminomethylation of 1,1-diaryl-allylalcohols. Conversion of these olefins with carbon monoxide, hydrogen and secondary amines proceeds with complete regioselectivity. This group can easily be removed under acidic and hydrogenating conditions, enabling the transformation of 4-amino-1,1-diarylbutan-1-ols to 4,4-diarylbutylamines in high yields. Thus Fluspirilene was synthesised in 88% yield in four steps starting from commercially available materials. (C) 2004 Elsevier Ltd. All rights reserved.