(R)-benzyl-(1-methyl-1-phenyl-but-3-enyl)amine | 897955-19-0

• 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: (R)-benzyl-(1-methyl-1-phenyl-but-3-enyl)amine
• 英文别名: (2R)-N-benzyl-2-phenylpent-4-en-2-amine
• CAS: 897955-19-0
• 化学式: C₁₈H₂₁N
• 分子量: 251.371
• InChiKey: RYFWJRLOQFKDHD-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-benzyl-(1-methyl-1-phenyl-but-3-enyl)amine 在 盐酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 (R)-(1-methyl-1-phenyl-but-3-enyl)amine
  参考文献：
  名称：

  Catalytic Enantioselective Allylation of Ketoimines

  摘要：

  A general catalytic allylation of simple ketoimines was developed using 1 mol % of CuF(.)3PPh(3) as catalyst, 1.5 mol % of La((OPr)-Pr-/)(3) as the cocatalyst, and stable and nontoxic allylboronic acid pinacol ester as the nucleophile. This reaction constituted a good template for developing the first catalytic enantioselective allylation of ketoimines. In this case, using (LiOPr)-Pr-i as the cocatalyst produced higher enantioselectivity and reactivity than La((OPr)-Pr-i)(3). Thus, using the CuF-cyclopentyl-DuPHOS complex ( 10 mol %) and (LiOPr)-Pr-i ( 30 mol %) in the presence of tBuOH (1 equiv) produced high enantioselectivity up to 93% ee from a range of aromatic ketoimines. Mechanistic studies indicated that (LiOPr)-Pr-i accelerates the reaction by increasing the concentration of an active nucleophile, allylcopper.

  DOI：

  10.1021/ja061510h
• 作为产物：
  描述：

  Benzenemethanamine, N-(1-phenylethylidene)-, (E)- 、 烯丙基硼酸频哪醇酯 在 CuF-1,2-bis[(S,S)-2,5-dicyclopentylphospholano]benzene 、 lithium isopropoxide 、 叔丁醇 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (S)-benzyl-(1-methyl-1-phenyl-but-3-enyl)amine 、 (R)-benzyl-(1-methyl-1-phenyl-but-3-enyl)amine
  参考文献：
  名称：

  Catalytic Enantioselective Allylation of Ketoimines

  摘要：

  A general catalytic allylation of simple ketoimines was developed using 1 mol % of CuF(.)3PPh(3) as catalyst, 1.5 mol % of La((OPr)-Pr-/)(3) as the cocatalyst, and stable and nontoxic allylboronic acid pinacol ester as the nucleophile. This reaction constituted a good template for developing the first catalytic enantioselective allylation of ketoimines. In this case, using (LiOPr)-Pr-i as the cocatalyst produced higher enantioselectivity and reactivity than La((OPr)-Pr-i)(3). Thus, using the CuF-cyclopentyl-DuPHOS complex ( 10 mol %) and (LiOPr)-Pr-i ( 30 mol %) in the presence of tBuOH (1 equiv) produced high enantioselectivity up to 93% ee from a range of aromatic ketoimines. Mechanistic studies indicated that (LiOPr)-Pr-i accelerates the reaction by increasing the concentration of an active nucleophile, allylcopper.

  DOI：

  10.1021/ja061510h

文献信息

• Catalytic Enantioselective Allylation of Ketoimines
  作者：Reiko Wada、Tomoyuki Shibuguchi、Sae Makino、Kounosuke Oisaki、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ja061510h

  日期：2006.6.1

  A general catalytic allylation of simple ketoimines was developed using 1 mol % of CuF(.)3PPh(3) as catalyst, 1.5 mol % of La((OPr)-Pr-/)(3) as the cocatalyst, and stable and nontoxic allylboronic acid pinacol ester as the nucleophile. This reaction constituted a good template for developing the first catalytic enantioselective allylation of ketoimines. In this case, using (LiOPr)-Pr-i as the cocatalyst produced higher enantioselectivity and reactivity than La((OPr)-Pr-i)(3). Thus, using the CuF-cyclopentyl-DuPHOS complex ( 10 mol %) and (LiOPr)-Pr-i ( 30 mol %) in the presence of tBuOH (1 equiv) produced high enantioselectivity up to 93% ee from a range of aromatic ketoimines. Mechanistic studies indicated that (LiOPr)-Pr-i accelerates the reaction by increasing the concentration of an active nucleophile, allylcopper.