2-[2H]-3-phenylpropanoic acid | 85020-80-0

• 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-[2H]-3-phenylpropanoic acid
• 英文别名: dl-2-Deuterio-3-phenyl-propionsaeure；α-deuterio-3-phenylpropionic acid；2-deuterio-3-phenyl-propionic acid；2-Deuterio-3-phenyl-propionsaeure；2-Deuterio-3-phenylpropanoic acid
• CAS: 85020-80-0
• 化学式: C₉H₁₀O₂
• 分子量: 151.169
• InChiKey: XMIIGOLPHOKFCH-WHRKIXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2-[2H]-3-phenylpropanoic acid
  参考文献：
  名称：

  215.基于氢的同位素区分的分子不对称性问题。尝试用Marckwald方法进行不对称合成

  摘要：

  DOI：

  10.1039/jr9480001085

文献信息

• Rhodium(I)-Catalyzed 1,4-Addition of Arylboronic Acids to Acrylic Acid in Water: One-Step Preparation of 3-Arylpropionic Acids
  作者：Bernhard Breit、Nicolas Vautravers

  DOI：10.1055/s-0030-1260319

  日期：2011.10

  A practical method for the one-step preparation of 3-arylpropionic acids through rhodium-catalyzed 1,4-addition of arylboronic acids to acrylic acid is reported. The method is applicable to a broad scope of aryl boronic acids and displays a wide functional group tolerance operating in water as the optimal reaction medium.

  报告了一种通过铑催化芳基硼酸与丙烯酸的 1,4- 加成一步制备 3-芳基丙酸的实用方法。该方法适用于多种芳基硼酸，在以水为最佳反应介质的条件下，具有广泛的官能团耐受性。
• Reversal of Enantioselectivity in the Hydroformylation of Styrene with [2<i>S,</i>4<i>S</i>-BDPP]Pt(SnCl₃)Cl at High Temperature Arises from a Change in the Enantioselective-Determining Step
  作者：Charles P. Casey、Susie C. Martins、Maureen A. Fagan

  DOI：10.1021/ja0318479

  日期：2004.5.1

  Deuterioformylation of styrene catalyzed by [(2S,4S)-BDPP]Pt(SnCl3)Cl at 39 degreesC gave 3-phenylpropanal (3) and 2-phenylpropanal (2) (n:i = 1.8, 71% ee (S)-2) with deuterium only beta to the aldehyde carbonyl and in the formyl group. Small amounts of deuterium were also found in the internal (2.8%), cis terminal (1.4%), and trans terminal (1.3%) vinyl positions of the recovered styrene. Deuterioformylation of styrene at 98 degreesC gave 3- (3) and 2-phenylpropanal (2) (n:i = 2.3, 10% ee (R)-2) with deuterium both alpha and beta to the aldehyde carbonyl and in the formyl group. Deuterium was also found in the internal (20%), cis terminal (12%), and trans terminal (12%) vinyl positions of the recovered styrene. These deuterioformylation results establish that platinum hydride addition to styrene is largely irreversible at 39 degreesC but reversible at 98 degreesC. Hydroformylation of (E)- and (Z)-beta-deuteriostyrene at 40 degreesC, followed by oxidation of the aldehydes to acids, and subsequent derivitization to the (S)-mandelate esters confirmed that 84% of 2-phenylpropanal (2) arises from platinum hydride addition to the si-face of styrene, while 73% of 3-phenylpropanal (3) arises from platinum hydride addition to the re-face of styrene. At 100 degreesC, the effect of variable H-2 and CO pressure on n:i, % ee, and TOF of hydroformylation of styrene was investigated. The results are consistent with enantioselectivity not being fully determined until the final hydrogenolysis of a platinum acyl intermediate.
• Isomerisation reaction of a gem-bis-trifluoromethyl olefin in a basic medium: a kinetic study
  作者：Marc Tordeux、Laurence Marival-Hodebar、Marie-Josée Pouet、Jean-Claude Halle、Claude Wakselman

  DOI：10.1016/s0022-1139(01)00446-8

  日期：2001.10

  The rearrangement of 5-phenyl-1,1,1-trifluoro-2-(trifluoromethyl)pent-2-ene to 5-phenyl-1,1,1-trifluoro-2-(trifluoromethyl)pent-3-ene has been studied by F-19 NMR in dimethylsulphoxide (DMSO). This isomerisation is catalysed by a base such as triethylamine. It is apparent that the olefin is more stable when the two trifluoromethyl groups are placed on a saturated carbon rather than on a vinylic carbon. In the isomerisation process, the part of triethylamine is to assist the intramolecular hydrogen transfer to give the more stable isomer. (C) 2001 Elsevier Science B.V. All rights reserved.
• Cobalt-catalyzed carbonylation of optically active and α-deuterated phenethyl halides
  作者：F. Francalanci、A. Gardano、L. Abis、T. Fiorani、M. Foà

  DOI：10.1016/0022-328x(83)80224-1

  日期：1983.2
• FRANCALANCI, F.;GARDANO, A.;ABIS, L.;FIORANI, T.;FOA, M., J. ORGANOMETAL. CHEM., 1983, 243, N 1, 87-94
  作者：FRANCALANCI, F.、GARDANO, A.、ABIS, L.、FIORANI, T.、FOA, M.

  DOI：——

  日期：——