(S)-3-(4-fluorophenyl)-2-hydroxypropionic acid | 124980-93-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-3-(4-fluorophenyl)-2-hydroxypropionic acid
• 英文别名: (2S)-3-(4-fluorophenyl)-2-hydroxypropanoic acid
• CAS: 124980-93-4
• 化学式: C₉H₉FO₃
• 分子量: 184.167
• InChiKey: YZDVNWXOYGTHJO-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-fluorophenyl)-2-hydroxypropionic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 17.0h， 以34.6%的产率得到(S)-3-(4-fluorophenyl)-1,2-propanediol
  参考文献：
  名称：

  嗜热古细菌的高度对映体选择性的立体转化仲烷基硫酸酯酶活性。

  摘要：

  使用需氧生长的嗜热硫代谢物的全细胞，如Sulfolobus solfataricus DSM 1617，Shiulfoloshishibatae DSM 5389，将rac-sec-烷基硫酸酯1a-8a分解为低至优异的对映选择性，E值高达> 200。最值得注意的是，Sulfolobus acidocaldarius DSM639。使用在富含蔗糖的Brock培养基上生长的细胞可以显着提高选择性。已显示该生物水解的立体化学过程在构型的严格颠倒下进行，因此优选的（R）-对映异构体被转化成相应的（S）-仲醇以提供均手性产物混合物。

  DOI：

  10.1039/b504883d
• 作为产物：
  描述：

  L-4-氟苯丙氨酸 在 硫酸 、 sodium nitrite 作用下， 以18%的产率得到(S)-3-(4-fluorophenyl)-2-hydroxypropionic acid
  参考文献：
  名称：

  嗜热古细菌的高度对映体选择性的立体转化仲烷基硫酸酯酶活性。

  摘要：

  使用需氧生长的嗜热硫代谢物的全细胞，如Sulfolobus solfataricus DSM 1617，Shiulfoloshishibatae DSM 5389，将rac-sec-烷基硫酸酯1a-8a分解为低至优异的对映选择性，E值高达> 200。最值得注意的是，Sulfolobus acidocaldarius DSM639。使用在富含蔗糖的Brock培养基上生长的细胞可以显着提高选择性。已显示该生物水解的立体化学过程在构型的严格颠倒下进行，因此优选的（R）-对映异构体被转化成相应的（S）-仲醇以提供均手性产物混合物。

  DOI：

  10.1039/b504883d

文献信息

• Biocatalytic Racemization of Aliphatic, Arylaliphatic, and Aromatic α-Hydroxycarboxylic Acids
  作者：Silvia M. Glueck、Monika Pirker、Bettina M. Nestl、Barbara T. Ueberbacher、Barbara Larissegger-Schnell、Katrin Csar、Bernhard Hauer、Rainer Stuermer、Wolfgang Kroutil、Kurt Faber

  DOI：10.1021/jo050156n

  日期：2005.5.1

  Biocatalytic racemization of a range of aliphatic, (aryl)aliphatic, and aromatic alpha-hydroxycarboxylic acids was accomplished by using whole resting cells of a range of Lactobacillus spp. The mild (physiological) reaction conditions ensured an essentially "clean" isomerization in the absence of side reactions, such as elimination or decomposition. Whereas straight-chain aliphatic 2-hydroxy-carboxylic acids were racemized with excellent rates (up to 85% relative to lactate), steric hindrance was observed for branched-chain analogues. Good rates were observed for aryl-alkyl derivatives, such as 3-phenyllactic acid (up to 59%) and 4-phenyl-2-hydroxybutanoic acid (up to 47%). In addition, also mandelate and its o-chloro analogue were accepted at a fair rate (45%). This biocatalytic racemization represents an important tool for the deracemization of a number of pharmaceutically important building blocks.
• ANTIPICORNAVIRAL COMPOUNDS, THEIR PREPARATION AND USE
  申请人：AGOURON PHARMACEUTICALS, INC.

  公开号：EP1073672A1

  公开（公告）日：2001-02-07
• VERFAHREN ZUR MIKROBIOLOGISCHEN ISOMERISIERUNG VON ALPHA-HYDROXYCARBONSÄUREN
  申请人：BASF Aktiengesellschaft

  公开号：EP1639119A1

  公开（公告）日：2006-03-29
• TEMPLATE-FIXED BETA-HAIRPIN PEPTIDOMIMETICS WITH CXCR4 ANTAGONIZING ACTIVITY
  申请人：Gombert Frank

  公开号：US20110312879A1

  公开（公告）日：2011-12-22

  Template-fixed peptidomimetics formula (Ia) formula (Ib) wherein Z is a template-fixed chain of 14 α-amino and/or α-hydroxy acid residues which, depending on their positions in the chain (counted starting from the N-terminal amino acid), are Pro, Gly, a glycolic acid residue or of certain types which, as the remaining symbols in the above formulae, are defined in the description and the claims, and salts thereof, have CXCR4 antagonizing properties and can be used for preventing HIV infections in non-infected individuals or for slowing and halting viral progression in infected patients; or where cancer is mediated or resulting from CXCR4 receptor activity; or where immunological diseases are mediated or resulting from CXCR4 receptor activity; or for treating immuno suppression; or during apheresis collections of peripheral blood stem cells and/or as agents to induce mobilization of stem cells to regulate tissue repair. These depsipeptides can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.
• US8883720B2
  申请人：——

  公开号：US8883720B2

  公开（公告）日：2014-11-11