(4S,7S)-4,7-Dicyclopentyl-[1,3,2]dioxathiepane 2,2-dioxide | 897955-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: (4S,7S)-4,7-Dicyclopentyl-[1,3,2]dioxathiepane 2,2-dioxide
• CAS: 897955-41-8
• 化学式: C₁₄H₂₄O₄S
• 分子量: 288.408
• InChiKey: MFAGRKZGKLTMPC-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,7S)-4,7-Dicyclopentyl-[1,3,2]dioxathiepane 2,2-dioxide 、 1,2-二(膦酰基)苯 在 正丁基锂 、 硼烷四氢呋喃络合物 、 三乙烯二胺 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 16.0h， 以198 mg的产率得到1,2-bis[(R,R)-2,5-dicyclopentylphospholano]benzene
  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 、 Rh on carbon titanium(IV) isopropylate 、 叔丁基过氧化氢 、 氯化亚砜 、 L-(+)-酒石酸二异丙酯 、 氢气 作用下， 以 甲醇 、 四氯化碳 、 癸烷 、 二氯甲烷 为溶剂， 20.0~40.0 ℃ 、5.07 MPa 条件下， 反应 61.0h， 生成 (4S,7S)-4,7-Dicyclopentyl-[1,3,2]dioxathiepane 2,2-dioxide
  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