isopropyl 2,3-dihydroxy-3-phenyl propanoic acid | 327969-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 2,3-dihydroxy-3-phenyl propanoic acid
• 英文别名: propan-2-yl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate
• CAS: 327969-13-1
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: GEQUXERDWIOTST-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  3-苯基-2-丙烯酸-1-甲乙酯 在 水 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 叔丁醇 为溶剂， 反应 6.0h， 以96%的产率得到isopropyl 2,3-dihydroxy-3-phenyl propanoic acid
  参考文献：
  名称：

  1,4-双（9-O-二氢奎宁基）邻苯二甲酰修饰的联萘基-纳米粒子催化的烯烃对映体选择性对羟基化反应

  摘要：

  一系列具有手性改性剂的前所未有的联萘-os纳米颗粒（OsNPs）被用于烯烃的异质不对称二羟基化反应中。揭示了取决于共价有机壳的密度，OsNP的显着的尺寸效应，其对二羟基化反应的反应性和对映选择性的影响。还证实了OsNPs的成功回收，并保持了高反应效率和对映选择性。

  DOI：

  10.1002/cctc.201701368

文献信息

• Wang, Qiao Feng; Sun, Xiao Li; Zhang, Sheng Yong, Croatica Chemica Acta, 2007, vol. 80, # 1, p. 41 - 44
  作者：Wang, Qiao Feng、Sun, Xiao Li、Zhang, Sheng Yong、Qin, Xiang Yang、Zhao, Yan

  DOI：——

  日期：——
• Lohray; Bhushan, Vidya; Reddy, G. Jaipal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 1, p. 161 - 168
  作者：Lohray、Bhushan, Vidya、Reddy, G. Jaipal、Reddy, A. Sekar

  DOI：——

  日期：——
• Catalytic asymmetric dihydroxylation of cis-disubstituted olefins
  作者：Lisa Wang、K. Barry Sharpless

  DOI：10.1021/ja00045a042

  日期：1992.9
• Concentration Dependence of the Sharpless Asymmetric Amidohydroxylation of Isopropyl Cinnamate
  作者：Peter G. M. Wuts、Andrew M. Anderson、Michael P. Goble、Sarah E. Mancini、Ronald J. VanderRoest

  DOI：10.1021/ol006198+

  日期：2000.8.1

  [GRAPHICS]A need to prepare large quantities of phenylisoserine for the semisynthesis of paclitaxel prompted us to examine the Sharpless amidohydroxylation reaction to see if it could be run at concentrations greater than those reported in the literature. During these investigations, we discovered that the amount of amidoalcohol produced in the reaction decreased while the diol side product increased as the concentration increased. We discovered that acetamide suppresses this side reaction and allows us to run the chemistry at 0.1 g/mL rather than the 0.014 g/mL reported in the literature.
• Heterogeneous asymmetric catalytic aminohydroxylation promoted by a bis-Cinchona alkaloid derivative supported onto an insoluble organic polymeric matrix
  作者：Alessandro Mandoli、Dario Pini、Andrea Agostini、Piero Salvadori

  DOI：10.1016/s0957-4166(00)00399-2

  日期：2000.10

  By using a bis(quinidinyl)phthalazine derivative linked to an insoluble organic polymer, 87% e.e. was obtained in the osmium-mediated catalytic heterogeneous asymmetric aminohydroxylation of isopropyl trans-cinnamate. The recycling of the polymeric ligand-osmium complex was also investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.