α-benzenessigsaeure-methylester | 17226-93-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: α-benzenessigsaeure-methylester
• 英文别名: methyl threo-3-hydroxy-2,3-diphenylpropanoate；anti-methyl 3-hydroxy-2,3-diphenylpropanoate；methyl anti-3-hydroxy-2,3-diphenylpropanoate；methyl 3-hydroxy-2,3-diphenyl propanoate；(2RS,3SR)-3-hydroxy-2,3-diphenyl-propionic acid methyl ester；(2RS,3SR)-3-Hydroxy-2,3-diphenyl-propionsaeure-methylester；methyl (2R,3S)-3-hydroxy-2,3-diphenylpropanoate
• CAS: 17226-93-6；17226-94-7；58769-52-1；58769-53-2；93434-58-3；120851-53-8；139628-23-2
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: DLFSYZUHQWKGDA-HUUCEWRRSA-N

物化性质

• 沸点：
  393.8±37.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-benzenessigsaeure-methylester 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 sodium azide 、 四丁基氟化铵 、 水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 1,2-Diphenyl-3-(triazol-1-yl)propan-1-one
  参考文献：
  名称：

  Discovery of a novel class of aldol-derived 1,2,3-triazoles: Potent and selective inhibitors of human cytochrome P450 19A1 (aromatase)

  摘要：

  The discovery of a novel five-component 1,2,3-triazole-containing pharmacophore that exhibits potent and selective inhibition of aromatase (CYP 450 19A1) is described. All compounds are derived from an initial aldol reaction of a phenylacetate derivative with an aromatic aldehyde. Structure-activity data generated from both syn- and anti-aldol adducts provides initial insights into the requirements for both potency and selectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.039
• 作为产物：
  描述：

  α-benzenessigsaeure 、 N,N-二甲基甲酰胺二甲基缩醛 生成 α-benzenessigsaeure-methylester
  参考文献：
  名称：

  MULZER, J.;BRUENTRUP, G., CHEM. BER., 1982, 115, N 6, 2057-2075

  摘要：

  DOI：

文献信息

• Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
  作者：P. Veeraraghavan Ramachandran、Prem B. Chanda

  DOI：10.1039/c3cc40860d

  日期：——

  enantioselective synthesis of anti- and syn-beta-hydroxy-alpha-phenyl carboxylates has been achieved by the proper choice of solvent, temperature, alkoxy group, and amine for the diisopinocampheylboron-mediated asymmetric enolization-aldolization of phenylacetates. The pure diastereomers can be readily separated by column chromatography.

  抗和SYN-β-羟基-α-苯基羧酸酯的试剂控制的，diastereo-和对映选择性合成已经通过溶剂，温度，烷氧基，胺为diisopinocampheylboron介导的非对称的烯醇化-缩醛反应的适当选择来实现苯乙酸酯。可以通过柱色谱法容易地分离纯的非对映异构体。
• Diastereoselective reactions of 1,1′-binaphthyl ester enolates with carbonyl electrophiles
  作者：Mija Ahn、Kiyoshi Tanaka、Kaoru Fuji

  DOI：10.1039/a706673b

  日期：——

  Diastereoselectivity in the aldol and the conjugate additions of 2′-hydroxy-1,1′-binaphthyl ester enolates with a variety of carbonyl electrophiles has been examined. The ester enolate generated by BuLi reacts with several aldehydes to give the threo products preferentially with high diastereoselectivity and in good yield. Satisfactory diastereoselectivity has also been observed in the minor erythro derivatives. A mechanistic interpretation of the results is made on the basis of the absolute stereochemistry of the products.

  已研究了2′-羟基-1,1′-联萘酯酮烯与多种羰基电烯的醇醛反应和结合加成反应中的二面体选择性。由BuLi生成的酯酮烯与几种醛反应，优先生成threo产物，具有高的二面体选择性和良好的收率。在少量的erythro衍生物中也观察到了令人满意的二面体选择性。根据产物的绝对立体化学，对结果进行了机制解释。
• Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate
  作者：P. Veeraraghavan Ramachandran、Prem B. Chanda

  DOI：10.1021/ol301782s

  日期：2012.9.7

  Unlike the enolboration-aldolization of methyl propanoate, the choice of either the solvent or temperature determines the diastereoselectivity during the enolboration-aldolization of methyl phenylacetate. In CH2Cl2, the reaction favors the anti-pathway at -78 degrees C and the syn-pathway at rt. Conversely, the reaction produces the anti-isomer up to rt and the syn-isomer at refluxing temperatures in nonpolar solvents.
• Overriding effect of temperature over reagent and substrate size for boron-mediated aldol reaction of methyl phenylacetate
  作者：P. Veeraraghavan Ramachandran、Prem B. Chanda

  DOI：10.1016/j.tetlet.2013.08.106

  日期：2013.10

  The enolization temperature overrides all other aspects, including the sterics of the alkyl group of the boron reagent and the alkoxy group of the ester during the enolboration-aldolization of phenylacetates. This study has led to the first n-Bu2BOTf-mediated anti-selective aldol reaction of an ester. (C) 2013 Elsevier Ltd. All rights reserved.
• Mulzer, Johann; Bruentrup, Gisela, Chemische Berichte, 1982, vol. 115, # 6, p. 2057 - 2075
  作者：Mulzer, Johann、Bruentrup, Gisela

  DOI：——

  日期：——