(S)-3-(4-chlorophenyl)-2-hydroxypropionic acid | 494796-54-2

• 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-chlorophenyl)-2-hydroxypropionic acid
• 英文别名: 4-chloro-L-phenyllactic acid；(2S)-3-(4-chlorophenyl)-2-hydroxypropanoic acid
• CAS: 494796-54-2
• 化学式: C₉H₉ClO₃
• 分子量: 200.622
• InChiKey: HWVHXAYPEXNZSZ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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

• 作为反应物：
  描述：

  (S)-3-(4-chlorophenyl)-2-hydroxypropionic acid 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 44.0h， 生成 (-)-1-(4-chloro-phenyl)-2-propanol
  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-氯苯丙氨酸 在 硫酸 、 sodium nitrite 作用下， 以20%的产率得到(S)-3-(4-chlorophenyl)-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

• Access to benzene-modified 2^nd generation strigolactams and GR24 by merging C–H olefination with decarboxylative Giese cyclization
  作者：Yuhua Ge、Xingyue Chen、Yi Dong、Hua-Nan Wang、Yangyan Li、Gang Chen

  DOI：10.1039/d1ob01234g

  日期：——

  Herein, we reported an efficient and general synthetic route to assemble benzene-modified 2^nd generation strigolactams and GR24. The key features of this synthesis include a palladium-catalyzed ortho-selective olefination and a decarboxylative Giese radical cyclization.

  在这里，我们报告了一种高效且通用的合成路线，用于组装苯改性的第二代异槲聚糖和GR24。这种合成的关键特点包括钯催化的正向选择性烯烃化和脱羧Giese自由基环化。
• Substituted piperazines and methods of use
  申请人：——

  公开号：US20030220324A1

  公开（公告）日：2003-11-27

  Selected substituted piperazine compounds are effective for prophylaxis and treatment of diseases, such as obesity and the like. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving activation of the melanocortin receptor. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  选择的替代哌嗪化合物对于预防和治疗疾病，如肥胖等，具有有效性。该发明涵盖了新型化合物、类似物、前药和其药用盐，以及用于预防和治疗涉及黑素皮质素受体激活的疾病和其他疾病或病症的药物组合物和方法。该发明还涉及制备这类化合物的方法，以及在这些过程中有用的中间体。
• [EN] SUBSTITUTED PIPERAZINES AS MODULATORS OF THE MELANOCORTIN RECEPTOR<br/>[FR] PIPERAZINES SUBSTITUEES COMME MODULATEURS DU RECEPTEUR DE MELANOCORTINE
  申请人：AMGEN INC

  公开号：WO2003009850A1

  公开（公告）日：2003-02-06

  Selected substituted piperazine compounds are effective for prophylaxis and treatment of diseases, such as obesity and the like. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving activation of the melanocortin receptor. The subject invention also relates to processes For making such compounds as well as to intermediates useful in such processes.

  选定的取代哌嗪化合物可用于预防和治疗疾病，如肥胖症等。该发明涵盖了新化合物、类似物、前药及其药学上可接受的盐、制药组合物以及用于预防和治疗涉及黑色素皮质素受体激活的疾病和其他疾病或病症的方法。该发明还涉及制造这些化合物的过程，以及在此类过程中有用的中间体。
• Substituted piperazinyl amides and methods of use
  申请人：Amgen Inc.

  公开号：US07115607B2

  公开（公告）日：2006-10-03

  Selected substituted piperazine compounds of Formula I are effective for prophylaxis and treatment of diseases, such as obesity and the like. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving activation of the melanocortin receptor. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  公式I中选择的取代哌嗪化合物对于预防和治疗肥胖症等疾病有效。本发明涵盖了新型化合物、类似物、前药和其药学上可接受的盐、药物组合物以及预防和治疗激活黑色素细胞受体相关的疾病和其他疾病或病情的方法。本发明还涉及制备这种化合物的过程以及在这种过程中有用的中间体。
• 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.