2-{(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,5-dihydro-oxazole | 917893-67-5

• 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: 2-{(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,5-dihydro-oxazole
• 英文别名: 2-[(4S,5R)-5-(2-diphenylphosphorylphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-4,5-dihydro-1,3-oxazole
• CAS: 917893-67-5
• 化学式: C₂₆H₂₆NO₄P
• 分子量: 447.471
• InChiKey: HAMZBDFZIPPSAI-RPWUZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,5-dihydro-oxazole 在 titanium(IV) isopropylate 、 三乙氧基硅烷 作用下， 以 苯 为溶剂， 反应 5.0h， 以32%的产率得到2-[(4S,5R)-5-(2-Diphenylphosphanyl-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4,5-dihydro-oxazole
  参考文献：
  名称：

  StePHOX, a new family of optically active, tunable phosphine–oxazoline ligands: syntheses and applications

  摘要：

  A new class of optically active phosphine-oxazoline ligands has been synthesized wherein backbone chirality of these new ligands is installed by a Sharpless asymmetric dihydroxylation. Different backbone protecting groups as well as different substitution patterns on the oxazoline ring were studied. These ligands were tested in allylic substitution (with ee's up to 97%) and asymmetric Tsuji allylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.043
• 作为产物：
  描述：

  (2S,3R)-2,3-Dihydroxy-3-(2-trifluoromethanesulfonyloxy-phenyl)-propionic acid ethyl ester 在 1,3-双(二苯基膦)丙烷 、 palladium diacetate 4-二甲氨基吡啶 、 对甲苯磺酸 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 38.0h， 生成 2-{(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,5-dihydro-oxazole
  参考文献：
  名称：

  StePHOX, a new family of optically active, tunable phosphine–oxazoline ligands: syntheses and applications

  摘要：

  A new class of optically active phosphine-oxazoline ligands has been synthesized wherein backbone chirality of these new ligands is installed by a Sharpless asymmetric dihydroxylation. Different backbone protecting groups as well as different substitution patterns on the oxazoline ring were studied. These ligands were tested in allylic substitution (with ee's up to 97%) and asymmetric Tsuji allylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.043