(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-[1,3]dioxolane-4-carboxylic acid ethyl ester | 917893-71-1

• 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: (4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-[1,3]dioxolane-4-carboxylic acid ethyl ester
• CAS: 917893-71-1
• 化学式: C₂₄H₂₃O₅P
• 分子量: 422.417
• InChiKey: DCFREQLXRCKWNT-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-[1,3]dioxolane-4-carboxylic acid ethyl ester 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 三乙氧基硅烷 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 24.0h， 生成 2-[(4S,5R)-5-(2-Diphenylphosphanyl-phenyl)-[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：

  香豆素 在 1,3-双(二苯基膦)丙烷 、 palladium diacetate 2,6-二甲基吡啶 、 甲基磺酰胺 、 AD-mix-β 、 水 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 、 叔丁醇 、 苯 为溶剂， 反应 86.0h， 生成 (4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-[1,3]dioxolane-4-carboxylic acid ethyl ester
  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