isopropyl 2,3-dihydroxy-3-phenyl propanoic acid | 299160-76-2

• 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: (2R,3S)-isopropyl 2,3-dihydroxy-3-phenylpropanoate；propan-2-yl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate
• CAS: 299160-76-2
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: GEQUXERDWIOTST-WDEREUQCSA-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 四氧化锇 、 bis((R)-((1S,2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl) isophthalate 、 水 、 potassium carbonate 、 O-(methylsulfonyl)hydroxylamine 、 potassium hexacyanoferrate(III) 作用下， 以 叔丁醇 为溶剂， 生成 isopropyl 2,3-dihydroxy-3-phenyl propanoic acid
  参考文献：
  名称：

  Cinchona alkaloid ester derivatives as ligands in the asymmetric dihydroxylation and aminohydroxylation of alkenes

  摘要：

  Cinchona alkaloid ester derivatives were adopted to asymmetric dihydroxylation and asymmetric aminohydroxylation reactions in excellent yields and enantiomeric excesses.

  DOI：

  10.1016/j.mencom.2010.03.013

文献信息

• Chiral-Substituted Poly-<i>N</i>-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions
  作者：Bo Hao、Medha J. Gunaratna、Man Zhang、Sahani Weerasekara、Sarah N. Seiwald、Vu T. Nguyen、Alex Meier、Duy H. Hua

  DOI：10.1021/jacs.6b12113

  日期：2016.12.28

  synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1

  由L-氨基酸合成了在吡咯烷酮环的C5处含有不对称中心的一类新的聚-N-乙烯基吡咯烷酮。这些聚合物，特别是17，用于稳定纳米团簇，例如Pd/Au，用于1,3-和1,2-环烷二醇和烯烃的催化不对称氧化，而Cu/Au用于环烷烃的CH氧化。研究发现，吡咯烷酮环中的C5取代基体积越大，产生的光学产率越大。 (±)-1,3- 和 1,2-反式环烷二醇的氧化动力学拆分以及内消旋顺式二醇的去对称化均在水中的氧气气氛下用 0.15 mol% Pd/Au (3:1)-17 进行，提供优异的 (S)-羟基酮的化学和光学收率。在 30 psi 氧气水中，用 0.5 mol% Pd/Au (3:1)-17 氧化各种烯烃，得到 >93% ee 的二羟基化产物。 (R)-柠檬烯在 25 °C 下在 C-1,2-环烯官能团处发生氧化，产生 (1S,2R,4R)-二羟基柠檬烯 49，产率 92%。重要的是，环烷烃用乙腈中的
• 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.
• Cinchona alkaloid ester derivatives as ligands in the asymmetric dihydroxylation and aminohydroxylation of alkenes
  作者：Hui Chen、Qiao Feng Wang、Xiao Li Sun、Jing Luo、Ru Jiang

  DOI：10.1016/j.mencom.2010.03.013

  日期：2010.3

  Cinchona alkaloid ester derivatives were adopted to asymmetric dihydroxylation and asymmetric aminohydroxylation reactions in excellent yields and enantiomeric excesses.