3-hydroxy-3-(3'-bromophenyl)propionic acid | 40620-67-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-hydroxy-3-(3'-bromophenyl)propionic acid
• 英文别名: 3-Bromo-I(2)-hydroxybenzenepropanoic acid；3-(3-bromophenyl)-3-hydroxypropanoic acid
• CAS: 40620-67-5
• 化学式: C₉H₉BrO₃
• 分子量: 245.073
• InChiKey: YXHYKPPAIDYCKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 3-(3-bromophenyl)-3-hydroxypropanoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以22%的产率得到3-hydroxy-3-(3'-bromophenyl)propionic acid
  参考文献：
  名称：

  Structures of racemic halogen-substituted 3-hydroxy-3-phenylpropionic acids; relations between spontaneously resolved and racemic compounds

  摘要：

  Low-temperature [122.0(5)K] X-ray diffraction data [lambda(CuK alpha) = 1.54184 Angstrom] showed that racemic 3-hydroxy-3-(3'-chlorophenyl)propionic acid and its bromo-substituted analogue are isostructural. 3-Hydroxy-3-(3'-chlorophenyl)propionic acid: C9H9ClO3, M(r) = 200.61, monoclinic, P2(1)/c, a = 15.301 (2), b = 5.7117 (8), c = 11.2462 (13)Angstrom, beta = 110.873 (10)degrees, V = 918.4 (2)Angstrom(3), Z = 4, D-x = 1.451 g cm(-3), mu = 35.15 cm(-1), F(000) = 416, wR(2) = 0.0775 for 1880 contributing reflections [R = 0.0274 for F > 4 sigma(F)], m.p. 342.7(5)K. 3-Hydroxy-3-(3'-bromophenyl)propionic acid: C9H9BrO3, M(r) = 245.07, monoclinic, P2(1)/c, a = 15.498 (3), b = 5.6513 (12), c = 11.298 (2)Angstrom, beta = 111.280 (14)degrees, V = 938.4 (3)Angstrom(3), Z = 4, D-x = 1.735 g cm(-3), mu = 58.07 cm(-1), F(000) = 488, wR(2) = 0.0769 for 1926 m.p. 348.7 (5)K. The results from these structure determinations were combined with results from crystal structure determinations of other halogen-substituted 3-hydroxy-3-phenylpropionic acids in an analysis performed to obtain insight into their conglomerate versus racemic compound formation. In all the structures studied, the O-H ... O hydrogen bonds are formed between identical donor and acceptor atoms leading to two distinct motifs. The crystallization of the racemates as either racemic compounds or mechanical mixtures of enantiomers can only be rationalized if weaker intermolecular interactions are taken into account.

  DOI：

  10.1107/s0108768194011663

文献信息

• Versatile Biocatalytic C(<i>sp</i>³)−H Oxyfunctionalization for the Site‐ Selective and Stereodivergent Synthesis of α‐ and β‐Hydroxy Acids
  作者：Yingle Mao、Weijie Zhang、Zunyun Fu、Yanqiong Liu、Lin Chen、Xin Lian、Dan Zhuo、Jiewei Wu、Mingyue Zheng、Cangsong Liao

  DOI：10.1002/anie.202305250

  日期：2023.8.14

  α-ketoglutarate-dependent aryloxyalkanoate dioxygenases (AADs) are repurposed for applications in biocatalytic oxyfunctionalization. Activity profiling of natural AADs enabled the synthesis of four types of α-and β-hydroxy acids with broad scope, high efficiency, and good selectivity.

  在此，α-酮戊二酸依赖性芳氧基链烷酸双加氧酶（AAD）被重新用于生物催化氧功能化中的应用。天然 AAD 的活性分析使得四种类型的α-和β-羟基酸的合成具有广泛、高效和良好的选择性。
• Optically active alkyl 3-aryl-3-hydroxypropionates and a method for producing thereof
  申请人：CHISSO CORPORATION

  公开号：EP0451668A2

  公开（公告）日：1991-10-16

  The invention relates to optically active alkyl 3-aryl-3-hydroxypropionates represented by the general formula: wherein R¹, R², R³, R ⁴ and R⁵ are hydrogen, hydroxyl, alkoxy of 1-4 carbon atoms, benzyloxy, flurorine, chlorine or bromine and R⁶ is alkyl, and a method for producing the above compounds.

  本发明涉及由通式表示的光学活性 3-芳基-3-羟基丙酸烷基酯： 其中 R¹、R²、R³、R⁴ 和 R⁵ 是氢、羟基、1-4 个碳原子的烷氧基、苄氧基、氟、氯或溴，R⁶ 是烷基、 以及生产上述化合物的方法。
• Process for the production of optically active alkyl 3-aryl-3-hydroxypropionates
  申请人：CHISSO CORPORATION

  公开号：EP0451668B1

  公开（公告）日：1997-08-13
• US5202457A
  申请人：——

  公开号：US5202457A

  公开（公告）日：1993-04-13
• Structures of racemic halogen-substituted 3-hydroxy-3-phenylpropionic acids; relations between spontaneously resolved and racemic compounds
  作者：S. Larsen、K. Marthi

  DOI：10.1107/s0108768194011663

  日期：1995.6.1

  Low-temperature [122.0(5)K] X-ray diffraction data [lambda(CuK alpha) = 1.54184 Angstrom] showed that racemic 3-hydroxy-3-(3'-chlorophenyl)propionic acid and its bromo-substituted analogue are isostructural. 3-Hydroxy-3-(3'-chlorophenyl)propionic acid: C9H9ClO3, M(r) = 200.61, monoclinic, P2(1)/c, a = 15.301 (2), b = 5.7117 (8), c = 11.2462 (13)Angstrom, beta = 110.873 (10)degrees, V = 918.4 (2)Angstrom(3), Z = 4, D-x = 1.451 g cm(-3), mu = 35.15 cm(-1), F(000) = 416, wR(2) = 0.0775 for 1880 contributing reflections [R = 0.0274 for F > 4 sigma(F)], m.p. 342.7(5)K. 3-Hydroxy-3-(3'-bromophenyl)propionic acid: C9H9BrO3, M(r) = 245.07, monoclinic, P2(1)/c, a = 15.498 (3), b = 5.6513 (12), c = 11.298 (2)Angstrom, beta = 111.280 (14)degrees, V = 938.4 (3)Angstrom(3), Z = 4, D-x = 1.735 g cm(-3), mu = 58.07 cm(-1), F(000) = 488, wR(2) = 0.0769 for 1926 m.p. 348.7 (5)K. The results from these structure determinations were combined with results from crystal structure determinations of other halogen-substituted 3-hydroxy-3-phenylpropionic acids in an analysis performed to obtain insight into their conglomerate versus racemic compound formation. In all the structures studied, the O-H ... O hydrogen bonds are formed between identical donor and acceptor atoms leading to two distinct motifs. The crystallization of the racemates as either racemic compounds or mechanical mixtures of enantiomers can only be rationalized if weaker intermolecular interactions are taken into account.