(R,R)-1,4-cyclopentyl-2-(E)-butene-1,4-diol | 897955-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R,R)-1,4-cyclopentyl-2-(E)-butene-1,4-diol
• CAS: 897955-37-2
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: OXGVDZWGLZTHIC-KYXFNPKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R,R)-1,4-cyclopentyl-2-(E)-butene-1,4-diol 在 Rh on carbon 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、5.07 MPa 条件下， 反应 4.0h， 以60%的产率得到(R,R)-1,4-cyclopentyl-1,4-butanediol
  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：

  1-环戊基-2-丙醇 在 Grubbs catalyst first generation titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 (R,R)-1,4-cyclopentyl-2-(E)-butene-1,4-diol
  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