(S)-(+)-2-(3'-chlorophenyl)propanoic acid | 14161-84-3

• 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)-(+)-2-(3'-chlorophenyl)propanoic acid
• 英文别名: (S)-2-(3-chlorophenyl)propanoic acid；(S)-2-(3-chloro-phenyl)-propionic acid；(S)-2-(3-Chlor-phenyl)-propionsaeure；(2S)-2-(3-chlorophenyl)propanoic Acid
• CAS: 14161-84-3
• 化学式: C₉H₉ClO₂
• 分子量: 184.622
• InChiKey: YRUBJDXEYFCYCX-LURJTMIESA-N

物化性质

• 熔点：
  69.5-72 °C
• 沸点：
  286.6±15.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 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

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  甲醇 、 (S)-(+)-2-(3'-chlorophenyl)propanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-methyl 2-(3-chlorophenyl)propanoate
  参考文献：
  名称：

  使用Rhodococcus sp。对映体选择性水解各种外消旋的α-取代的芳基乙腈。CGMCC 0497

  摘要：

  Rhodococcus sp。对映体选择性水解17种外消旋的α-取代的芳基乙腈。描述了CGMCC 0497。在大多数情况下，以优异的对映体过量获得相应的（R）-酰胺和（S）-酸。此处讨论了空间和电子因素对反应结果的影响。结果证明腈转化酶是用于合成空间上不受阻碍的手性α-芳基丙酸和酰胺的有效工具。

  DOI：

  10.1016/s0957-4166(02)00017-4
• 作为产物：
  描述：

  间氯溴苯 在 C₄₈H₅₀Cl₄N₂O₂P₂Ru₃ 、 氢气 、 碘 、 双(三甲基硅烷基)氨基钾 、 碳酸氢钠 、 magnesium 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， -78.0~80.0 ℃ 、500.01 kPa 条件下， 反应 31.0h， 生成 (S)-(+)-2-(3'-chlorophenyl)propanoic acid
  参考文献：
  名称：

  钌烯基膦-恶唑啉-钌配合物催化α-取代丙烯酸的不对称加氢

  摘要：

  在5 bar H 2下，使用RuPHOX-Ru作为手性催化剂，对各种α-取代的丙烯酸进行不对称氢化，从而以高达99％的收率和99.9％ee的产率提供相应的手性α-取代的丙酸。该反应可以以克级进行，具有相对较低的催化剂负载量（最高5000 S / C），所得产物（97％，99.3％ee）可用作构建生物活性手性分子的关键中间体。该不对称方案已成功应用于二氢青蒿酸的不对称合成，这是抗疟疾药物青蒿素工业合成所需的关键中间体。

  DOI：

  10.1021/acs.orglett.6b00748

文献信息

• Deracemizing α‐Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis‐Silyl Ketene Acetals with Water or Methanol
  作者：Francesca Mandrelli、Aurélie Blond、Thomas James、Hyejin Kim、Benjamin List

  DOI：10.1002/anie.201905623

  日期：2019.8.12

  protonation of bis‐silyl ketene acetals. Our method delivers α‐branched carboxylic acids, including nonsteroidal anti‐inflammatory arylpropionic acids such as Ibuprofen, in high enantiomeric purity and high yields. The process can be incorporated in an overall deracemization of α‐branched carboxylic acids, involving a double deprotonation and silylation followed by the catalytic asymmetric protonation.

  我们报道了双硅基乙烯酮缩醛的高度对映选择性催化质子化。我们的方法可提供高对映体纯度和高收率的α-支链羧酸，包括非甾体抗炎性芳基丙酸（如布洛芬）。该过程可以纳入α-支链羧酸的整体脱硝过程，包括双重脱质子化和甲硅烷基化，然后进行催化不对称质子化。
• Enantioselective synthesis of α-methyl carboxylic acids using a DiTOX chiral auxiliary
  作者：Philip C Bulman Page、Michael J McKenzie、Steven M Allin、Sukhbinder S Klair

  DOI：10.1016/s0040-4020(97)00837-5

  日期：1997.9

  Five α-methyl carboxylic acids have been prepared with high e.e.s using 1,3-dithiane 1-oxide (DiTOX) units as the stereocontrolling elements and sources of chirality.

  使用1，3-二硫杂环丁烷1氧化物（DiTOX）单元作为立体控制元素和手性来源，已制备了五种高ee度的α-甲基羧酸。
• Ferrocenyl chiral bisphosphorus ligands for highly enantioselective asymmetric hydrogenation via noncovalent ion pair interaction
  作者：Caiyou Chen、Heng Wang、Zhefan Zhang、Shicheng Jin、Songwei Wen、Jianjian Ji、Lung Wa Chung、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1039/c6sc01845a

  日期：——

  (ee up to 99%, TON up to 20 000) for the asymmetric hydrogenation of both 2-aryl and 2-alkyl acrylic acids through ion pair noncovalent interaction under base free and mild reaction conditions. Well-known anti-inflammatory drugs such as naproxen and ibuprofen together with the intermediate for the preparation of Roche ester and some bioactive compounds were also efficiently obtained with excellent ee

  开发了新型的二茂铁基手性双磷配体Wudaphos，它具有优异的ee和活性（ee高达99％，TON高达20000），用于2-芳基和2-烷基丙烯酸通过离子的不对称氢化在无碱和温和的反应条件下配对非共价相互作用。还以优异的ee效率有效地获得了著名的消炎药，如萘普生和布洛芬，以及用于制备罗氏酯和某些生物活性化合物的中间体。进行了对照实验，发现离子对非共价相互作用和链长起着重要作用。
• Development of <i>C</i>₂-Symmetric Chiral Diphosphine Ligands for Highly Enantioselective Hydrogenation Assisted by Ion Pairing
  作者：Jianfei Yu、Haowei Zhu、Xumu Zhang、Gen-Qiang Chen

  DOI：10.1021/acs.orglett.2c00852

  日期：2022.4.15

  A new series of C2-symmetrical chiral ferrocene-based diphosphino-ethane ligands termed as f-DPE were developed. Assisted by the ion pairing interaction with the ligand, a wide scope of 2-substituted acrylic acids was hydrogenated to obtain chiral propanoic acids with high yields and enantioselectivities. The well-known anti-inflammatory drugs ibuprofen, naproxen, and flurbiprofen could be synthesized

  开发了一系列新的C 2 -对称手性二茂铁基二膦基乙烷配体，称为 f-DPE。在与配体的离子对相互作用的帮助下，广泛的 2-取代丙烯酸被氢化以获得高产率和对映选择性的手性丙酸。可以有效合成著名的抗炎药布洛芬、萘普生和氟比洛芬。此外，通过克级实验证明了当前方法的合成效用。
• 99mTc-sestamibi muscle scintigraphy to assess the response to neuromuscular electrical stimulation of normal quadriceps femoris muscle
  作者：Yeşim Pekindil、Ali Sarikaya、Murat Birtane、Gökhan Pekindil、Ahmet Salan

  DOI：10.1007/bf02988252

  日期：2001.8

  Objectives: Neuromuscular electrical stimulation (NMES) is widely used for improving muscle strength by simultaneous contraction in the prevention of muscle atrophy. Although there exist many clinical methods for evaluating the therapeutic response of muscles, Tc-99m-sestamibi which is a skeletal muscle perfusion and metabolism agent has not previously been used for this purpose. The aim of our work was to ascertain whether Tc-99m-sestamibi muscle scintigraphy is useful in the monitoring of therapeutic response to NMES in healthy women.Methods: The study included 16 women aged between 21 and 45, with a mean age of 32.7 +/- 6.4. Both quadriceps femoris muscles (QFM) of each patient were studied. After randomization to remove the effect of the dominant side, one QFM of each patient was subjected to the NMES procedure for a period of 20 days. NMES was performed with an alternating biphasic rectangular current, from a computed electrical stimulator daily for 23 minutes. After measurement of skinfold thickness over the thigh, pre- and post-NMES girth measurements were assessed in centimeters. Sixty minutes after injections of 555 MBq Tc-99m-sestamibi, static images of the thigh were obtained for 5 minutes. The thigh-to-knee uptake ratio was calculated by semiquantitative analysis and normalized to body surface area (NUR = normalized uptake ratio).Results: The difference between the pre and post NMES NUR values was Significant (1.76 +/- 0.31 versus 2.25 +/- 0.38, p = 0.0000). The percentage (%) increase in NUR values also well correlated with the % increase in thigh girth measurements (r = 0.89, p = 0.0000).Conclusion: These results indicated that Tc-99m-sestamibi muscle scintigraphy as a new tool may be useful in evaluating therapeutic response to NMES.