(2S)-2,3-dihydroxypropyl methacrylate | 96557-24-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2S)-2,3-dihydroxypropyl methacrylate
• 英文别名: 2,3-dihydroxypropyl methacrylate；[(2R)-2,3-dihydroxypropyl] 2-methylprop-2-enoate
• CAS: 96557-24-3
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: QRIMLDXJAPZHJE-ZCFIWIBFSA-N

物化性质

• 沸点：
  85-86 °C(Press: 0.025 Torr)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S)-2,3-(isopropylidenedioxy)propyl methacrylate 在 溶剂黄146 、 4-甲氧基苯酚 作用下， 反应 0.17h， 以80%的产率得到(2S)-2,3-dihydroxypropyl methacrylate
  参考文献：
  名称：

  Transition-metal-catalyzed asymmetric organic synthesis via polymer-attached optically active phosphine ligands. 13, Asymmetric hydrogenation with polymer catalysts containing primary and chiral secondary pendant alcohols

  摘要：

  DOI：

  10.1021/jo00213a020

文献信息

• Enantiopure poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate): a new material for supported catalytic asymmetric hydrogen transfer reduction
  作者：Alice Rolland、Damien Hérault、François Touchard、Christine Saluzzo、Raphaël Duval、Marc Lemaire

  DOI：10.1016/s0957-4166(01)00129-x

  日期：2001.4

  dimethacrylate afforded crosslinked copolymer 1 in high yield. Optically active polymers containing amino alcohol functionalities were then formed from 1 through epoxide ring opening with a number of achiral and homochiral amines. It was shown that ruthenium complexes based on these new polymeric amino alcohol ligands were effective catalysts for the asymmetric hydrogen transfer reduction of acetophenone.

  制备了一种含有手性环氧残基的新型共聚物。（R）-或（S）-甲基丙烯酸缩水甘油酯与乙二醇二甲基丙烯酸酯的自由基引发的悬浮共聚提供了高收率的交联共聚物1。然后从1至环氧化物开环，与许多非手性和同手性胺形成含氨基醇官能团的旋光聚合物。结果表明，基于这些新的聚合氨基醇配体的钌配合物是有效的催化剂，用于苯乙酮的不对称氢转移还原。
• Chiral polyamino alcohols and polyamino thiols for asymmetric heterogeneous catalysis
  作者：Damien Hérault、Christine Saluzzo、Marc Lemaire

  DOI：10.1016/j.tetasy.2006.06.041

  日期：2006.8

  A series of macroporous copolymer beads were synthesized by THE free radical suspension copolymerization of (S)-glycidylmethacrylate (GMA), (S)-thiiranylmethylmethacrylate (TMA), or (R,R)-phenylglycidylmethacrylate (Ph-GMA) with ethyleneglycol dimethacrylate (EDMA) or divinylbenzene (DVB). This allowed for the evaluation of their chemical and physical properties (polymer matrix nature or the structure of the heterocyclopropane) and their influence on the catalytic efficiency. These chiral polymers were subsequently transformed into polyamino alcohol or polyamino thiol derivatives by the facile ring opening of the oxirane or thiirane group with benzylamine and methylamine. Complexed with [RuCl2(P-cymene)](2), these derivatives were shown to be effective in the asymmetric hydrogen transfer reduction of acetophenone. The best results (conversion: 94%, ee: 71%) were obtained with benzylamine grafted onto poly(GMA-co-EDMA) (30/70 % wt/wt). (c) 2006 Published by Elsevier Ltd.
• DESCHENAUX, R.;STILLE, J. K., J. ORG. CHEM., 1985, 50, N 13, 2299-2302
  作者：DESCHENAUX, R.、STILLE, J. K.

  DOI：——

  日期：——
• Transition-metal-catalyzed asymmetric organic synthesis via polymer-attached optically active phosphine ligands. 13, Asymmetric hydrogenation with polymer catalysts containing primary and chiral secondary pendant alcohols
  作者：Robert Deschenaux、John K. Stille

  DOI：10.1021/jo00213a020

  日期：1985.6