alpha-(Trifluoromethyl)-alpha-methoxy-4-bromobenzenemethanamine | 842169-81-7

• 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: alpha-(Trifluoromethyl)-alpha-methoxy-4-bromobenzenemethanamine
• 英文别名: 1-(4-bromophenyl)-2,2,2-trifluoro-1-methoxyethanamine
• CAS: 842169-81-7
• 化学式: C₉H₉BrF₃NO
• 分子量: 284.076
• InChiKey: AMIGRZNCNHGQIB-UHFFFAOYSA-N

物化性质

• 沸点：
  299.8±40.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  alpha-(Trifluoromethyl)-alpha-methoxy-4-bromobenzenemethanamine 在 (R)-tetrahydro-1-n-butyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole 、 儿萘酚硼烷 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 (R)-1-(4-溴苯基)-2,2,2-三氟乙胺
  参考文献：
  名称：

  Synthesis of alpha fluoroalkyl amines

  摘要：

  该发明描述了α-氟烷基酮与双（三烷基硅基）酰胺反应，生成稳定的N-三烷基硅基亚胺。将N-三烷基硅基亚胺与醇处理，可使三烷基硅基团溶解并高产率地生成氨基醛和亚胺的稳定混合物。在手性催化剂存在下，对该混合物或单独的组分进行催化还原，可高选择性和高产率地得到氟烷基胺。

  公开号：

  US20060052642A1
• 作为产物：
  描述：

  4'-溴-2,2,2-三氟苯乙酮 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 生成 alpha-(Trifluoromethyl)-alpha-methoxy-4-bromobenzenemethanamine
  参考文献：
  名称：

  Unprecedented Catalytic Asymmetric Reduction of N−H Imines

  摘要：

  Addition of lithium bis(trimethylsilyl)amide to perfluorinated ketones 1a-j affords (E)-N-TMS-ketimines 2a-j that are reduced in situ to afford racemic perfluoromethylated amine hydrochloride salts 3a-j in 54-97% yields. Solvolysis of the N-Si bond in MeOH leads to formation of bench-stable, isolable N-H imine Z/E isomer mixtures along with a methanol adduct. Enantioselective reduction of these three-component mixtures provides the first catalytic asymmetric synthesis of trifluoromethylated amines in 72-95% yields and 75-98% ee.

  DOI：

  10.1021/ol047431x

文献信息

• Unprecedented Catalytic Asymmetric Reduction of N−H Imines
  作者：Francis Gosselin、Paul D. O'Shea、Stéphanie Roy、Robert A. Reamer、Cheng-yi Chen、Ralph P. Volante

  DOI：10.1021/ol047431x

  日期：2005.1.1

  Addition of lithium bis(trimethylsilyl)amide to perfluorinated ketones 1a-j affords (E)-N-TMS-ketimines 2a-j that are reduced in situ to afford racemic perfluoromethylated amine hydrochloride salts 3a-j in 54-97% yields. Solvolysis of the N-Si bond in MeOH leads to formation of bench-stable, isolable N-H imine Z/E isomer mixtures along with a methanol adduct. Enantioselective reduction of these three-component mixtures provides the first catalytic asymmetric synthesis of trifluoromethylated amines in 72-95% yields and 75-98% ee.
• Synthesis of alpha fluoroalkyl amines
  申请人：O'Shea Paul

  公开号：US20060052642A1

  公开（公告）日：2006-03-09

  This invention describes the reaction of an alpha fluoroalkyl ketone with a bis(trialkylsilyl)amide to give a stable N-trialkylsilyl imine. Treatment of the N-trialkylsilyl imine with an alcohol leads to solvolysis of the trialkylsilyl group and yields a stable mixture of an aminal and an imine in high yield. Catalytic reduction of this mixture, or of the individual components, in the presence of a chiral catalyst leads to a fluoroalkyl amine with high enantioselectivity and high yield.

  该发明描述了α-氟烷基酮与双（三烷基硅基）酰胺反应，生成稳定的N-三烷基硅基亚胺。将N-三烷基硅基亚胺与醇处理，可使三烷基硅基团溶解并高产率地生成氨基醛和亚胺的稳定混合物。在手性催化剂存在下，对该混合物或单独的组分进行催化还原，可高选择性和高产率地得到氟烷基胺。