2-[[(2S)-1-(2-diphenylphosphanyl-6-methoxyphenyl)pyrrolidin-2-yl]methyl-(2-hydroxyethyl)amino]ethanol | 581095-21-8

• 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-[[(2S)-1-(2-diphenylphosphanyl-6-methoxyphenyl)pyrrolidin-2-yl]methyl-(2-hydroxyethyl)amino]ethanol
• CAS: 581095-21-8
• 化学式: C₂₈H₃₅N₂O₃P
• 分子量: 478.571
• InChiKey: UOGNTCZCPQRIIC-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  月桂酰氯 、 2-[[(2S)-1-(2-diphenylphosphanyl-6-methoxyphenyl)pyrrolidin-2-yl]methyl-(2-hydroxyethyl)amino]ethanol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以81%的产率得到2-[[(2S)-1-(2-diphenylphosphanyl-6-methoxyphenyl)pyrrolidin-2-yl]methyl-(2-dodecanoyloxyethyl)amino]ethyl dodecanoate
  参考文献：
  名称：

  不使用氟溶剂的不对称烯丙基烷基化的氟钯催化剂的合成，反应和回收

  摘要：

  由（S）-脯氨醇制备带有两个氟马尾的手性氟氨基膦4c，并用高丙二酸二烷基酯-BSA-LiOAc体系应用于钯催化的1,3-二苯-2-丙烯乙酸丙烯酯（7）的钯催化不对称烯丙基烷基化。对映选择性（高达97％ee）。结果表明，通过简单的固/液分离，容易将配体4c的手性氟钯催化剂从反应混合物中分离出来，最多可重复使用5次。

  DOI：

  10.1021/jo051035q
• 作为产物：
  描述：

  (3R)-3-Bromo-1-[2-(diphenylphosphinyl)-6-methoxyphenyl]piperidine 在 三氯硅烷 、 potassium carbonate 、 三乙胺 作用下， 以 间二甲苯 、 乙腈 为溶剂， 反应 12.0h， 生成 2-[[(2S)-1-(2-diphenylphosphanyl-6-methoxyphenyl)pyrrolidin-2-yl]methyl-(2-hydroxyethyl)amino]ethanol
  参考文献：
  名称：

  Amination of N-Aryl Prolinol via Ring Expansion and Contraction:  Application to the Chiral Ligand for the Catalytic Asymmetric Reaction

  摘要：

  Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (11) with a dialkyl malonate-BSA-LiOAc system was successfully carried out with good enantioselectivities (up to 98% ee).

  DOI：

  10.1021/jo0479967

文献信息

• Chiral diaminophosphine ligands with stable C(aryl)N(amine) axial chirality derived from prolinol
  作者：Takashi Mino、Youichi Tanaka、Yutaka Sato、Akio Saito、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/s0040-4039(03)01097-9

  日期：2003.6

  New type chiral ligands 3, which have a chiral carbon center and stable C(aryl)-N(amine) axial chirality, were prepared from chiral prolinol-derived aminophosphine oxide 4. Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (6) with a dimethyl malonate-BSA-LiOAc system was successfully carried out in the presence of 3d resulting in a good yield with good enantioselectivity (up to 95% ee). (C) 2003 Elsevier Science Ltd. All rights reserved.
• Amination of <i>N</i>-Aryl Prolinol via Ring Expansion and Contraction:  Application to the Chiral Ligand for the Catalytic Asymmetric Reaction
  作者：Takashi Mino、Akio Saito、Youichi Tanaka、Shintaro Hasegawa、Yutaka Sato、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1021/jo0479967

  日期：2005.3.1

  Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (11) with a dialkyl malonate-BSA-LiOAc system was successfully carried out with good enantioselectivities (up to 98% ee).
• Synthesis, Reaction, and Recycle of Fluorous Palladium Catalysts for an Asymmetric Allylic Alkylation without Using Fluorous Solvents
  作者：Takashi Mino、Yutaka Sato、Akio Saito、Youichi Tanaka、Hiroaki Saotome、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1021/jo051035q

  日期：2005.9.1

  (7) with a dialkyl malonate-BSA-LiOAc system with high enantioselectivities (up to 97% ee). Results indicated that the chiral fluorous palladium catalyst from ligand 4c was easily separated from the reaction mixture by simple solid/liquid separation and could be reused up to five times.

  由（S）-脯氨醇制备带有两个氟马尾的手性氟氨基膦4c，并用高丙二酸二烷基酯-BSA-LiOAc体系应用于钯催化的1,3-二苯-2-丙烯乙酸丙烯酯（7）的钯催化不对称烯丙基烷基化。对映选择性（高达97％ee）。结果表明，通过简单的固/液分离，容易将配体4c的手性氟钯催化剂从反应混合物中分离出来，最多可重复使用5次。