1-[3,5-bis(trifluoromethyl)phenyl]-3-[(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]urea | 1392097-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]urea
• CAS: 1392097-67-4
• 化学式: C₂₉H₃₀F₆N₄O₂
• 分子量: 580.573
• InChiKey: QFNHRSQBCKXRJX-BZXROKRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,5-双(三氟甲基)苯基异氰酸酯 、 (6-甲氧基-4-喹啉基)-(5-乙烯基奎宁环-2-基)甲胺 以 四氢呋喃 为溶剂， 以43%的产率得到1-[3,5-bis(trifluoromethyl)phenyl]-3-[(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]urea
  参考文献：
  名称：

  Organocatalytic Enantioselective Formal C(sp²)–H Alkylation

  摘要：

  An organocatalytic enantioselective formal C(sp(2))-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.

  DOI：

  10.1021/ja5117556
• 作为试剂：
  描述：

  丙酮酸乙酯 、 2-azido-1-(3-methoxyphenyl)ethanone 在 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]urea 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以68%的产率得到
  参考文献：
  名称：

  Asymmetric aldol addition of α-azido ketones to ethyl pyruvate mediated by a cinchona-based bifunctional urea catalyst

  摘要：

  The first asymmetric synthesis of ethyl 4-aryl-3-azido-2-hydroxy-2-methyl-4-oxobutanoates via a cinchona organocatalyst induced aldol addition of alpha-azido ketones to ethyl pyruvate has been developed. The coupling reaction under optimized conditions was carried out to furnish tetrafunctionalized synthons with enantioselectivities of up to 91:9 and enriched diastereoselectivities of up to 95:5 (syn:anti). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.018

文献信息

• Organocatalytic Enantioselective Formal C(sp²)–H Alkylation
  作者：Madhu Sudan Manna、Santanu Mukherjee

  DOI：10.1021/ja5117556

  日期：2015.1.14

  An organocatalytic enantioselective formal C(sp(2))-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.