(RS)-2-phenoxyisovaleric acid | 13794-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RS)-2-phenoxyisovaleric acid
• 英文别名: α-Phenoxy-isovaleriansaeure；3-Methyl-2-phenoxy-buttersaeure；α-phenoxy-isovaleric acid；3-Methyl-2-phenoxybutanoic acid
• CAS: 13794-02-0
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD05863711
• 分子量: 194.23
• InChiKey: SACSRILQPQYFIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  304.5±15.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  (RS)-2-phenoxyisovaleric acid 在 五氯化磷 作用下， 生成 3-甲基-2-苯氧基丁酰氯
  参考文献：
  名称：

  A Primary Care Intervention for Depression

  摘要：

  Abstract: To assess a guideline‐based intervention's impact on depression care provided in rural vs. urban primary care settings, 12 community primary care practices (four rural, eight urban) were randomized to enhanced (i.e, intervention) and usual care study conditions. The study enrolled 479 depressed patients, with 432 (90.2 percent) completing telephone follow‐up at six months. Multilevel analytic models revealed that rural enhanced care patients had 2.70 times the odds (P=0.02) of rural usual care patients of taking a three‐month course of antidepressant medication at recommended dosages in the six months following baseline; urban enhanced care patients had 2.43 times the odds compared with their urban usual care counterparts (P=0.007). Rural enhanced care patients had 3.00 times the odds of rural usual care patients of making eight or more visits to a mental health specialist for counseling in the six months following baseline (P=0.03). Comparisons of patients in enhanced care practices showed that rural enhanced care patients had 2.00 times the odds (P=0.12) of urban enhanced care patients of making at least one visit to a mental health specialist for counseling in the six months following baseline and had comparable odds to urban enhanced care patients (odds ratio [OR] = 1.06, P=0.77) of making eight or more visits to such specialists during that interval. The study's intervention improved the care received by both rural and urban depressed primary care patients. Moreover, the interventions effect appears to have been greater in rural settings, particularly in terms of increasing depressed rural patients' use of mental health specialists for counseling.

  DOI：

  10.1111/j.1748-0361.2000.tb00482.x
• 作为产物：
  描述：

  3-methyl-2-phenoxybut-2-enoic acid 在 palladium on activated charcoal 氢气 作用下， 生成 (RS)-2-phenoxyisovaleric acid
  参考文献：
  名称：

  796.不饱和系统。第四部分的。邻的-Claisen重排α -和γ -芳氧基-β-methylcrotonates和α -苯氧基- γ -methylcrotonate

  摘要：

  DOI：

  10.1039/jr9630004210

文献信息

• Engineering the Promiscuous Racemase Activity of an Arylmalonate Decarboxylase
  作者：Robert Kourist、Yusuke Miyauchi、Daisuke Uemura、Kenji Miyamoto

  DOI：10.1002/chem.201001924

  日期：2011.1.10

  Variant G74C of arylmalonate decarboxylase (AMDase) from Bordatella bronchoseptica has a unique racemising activity towards profens. By protein engineering, variant G74C/V43A with a 20‐fold shift towards promiscuous racemisation was obtained, based on a reduced activity in the decarboxylation reaction and a two‐fold increase in the racemisation activity. The mutant showed an extended substrate range

  支气管败血波氏杆菌中的芳基丙二酸脱羧酶（AMDase）G74C变体对profens具有独特的消旋作用。通过蛋白质工程，基于脱羧反应的活性降低和消旋活性的两倍提高，获得了向混杂消旋化20倍的变体G74C / V43A。该突变体显示出扩大的底物范围，对酮洛芬的反应速率提高了30倍。分子动力学模拟和消旋酶的底物特征表明，底物结构的空间和极性效应在催化方面比单纯的动力学α-质子酸度起着更大的作用。β，γ-不饱和羧酸的转化不会导致重排形成其α，β异构体的观察结果表明，这是一个协调的机制，而不是逐步的机制。有趣的是，
• Access to Optically Enriched α-Aryloxycarboxylic Esters via Carbene-Catalyzed Dynamic Kinetic Resolution and Transesterification
  作者：Bin Liu、Runjiang Song、Jun Xu、Pankaj Kumar Majhi、Xing Yang、Song Yang、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1021/acs.orglett.0c00748

  日期：2020.5.1

  Disclosed here is a carbene-catalyzed dynamic kinetic resolution and transesterification reaction for access to this class of molecules with up to 99% yields and 99:1 er values. Addition of a chiral carbene catalyst to the ester substrate leads to two diastereomeric azolium ester intermediates that can quickly epimerize to each other and thus allows for effective dynamic kinetic resolution to be realized

  光学活性α-芳氧基羧酸及其衍生物是重要的功能分子。这里公开了一种卡宾催化的动态动力学拆分和酯交换反应，用于以高达 99% 的产率和 99:1 的 er 值获得这类分子。将手性卡宾催化剂添加到酯底物中会产生两种非对映体唑鎓酯中间体，它们可以快速彼此差向异构化，从而实现有效的动态动力学拆分。我们反应中的光学富集酯产物可以快速转化为手性除草剂和其他生物活性分子。
• Kinetic Resolution of α-Substituted Alkanoic Acids Promoted by Homobenzotetramisole
  作者：Xing Yang、Vladimir B. Birman

  DOI：10.1002/chem.201101028

  日期：2011.9.26

  classes of substrates, namely, α‐aryl‐, α‐aryloxy/alkoxy‐, α‐halo‐, α‐azido‐, and α‐phthalimido‐alkanoic acids. Under similar conditions, α‐(arylthio/alkylthio)‐alkanoic acids undergo dynamic kinetic resolution providing corresponding esters in up to 92 % ee and up to 93 % yield.

  已经开发出了一种新的催化α-取代链烷酸非酶催化动力学拆分的方法，该方法依赖于它们被DCC​​活化，然后在基于idine的催化剂均苯并四咪唑（HBTM）存在下对中间酸酐的对映选择性醇解。在几类底物的情况下（α-芳基，α-芳氧基/烷氧基，α-卤代，α-叠氮基和α）获得了中等至优异的选择性因子（s = 5-96）。邻苯二甲酰亚胺基链烷酸。在相似的条件下，α-（芳硫基/烷硫基）-链烷酸会经历动态动力学拆分，从而以高达92％ee的收率和高达93％的收率提供相应的酯 。
• HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases
  作者：A. A. Tumashov、S. A. Vakarov、L. Sh. Sadretdinova、E. N. Chulakov、G. L. Levit、V. P. Krasnov、V. N. Charushin

  DOI：10.1007/s11172-021-3165-8

  日期：2021.5

  reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.

  通过正相和反相 HPLC 在流行的手性固定相上研究了分离许多具有实际意义的 2-芳氧基羧酸的对映异构体的可能性。在正相 HPLC 条件下，使用多糖基 Chiralcel OD-H 和 Chiralpack AD 的手性相实现了最佳分离参数。使用制备型手性 HPLC 分离对映体过量 ee > 99% 的 2-(1-萘氧基)-和 2-(2-碘苯氧基)丙酸的 (S)-和 (R)-对映体。
• Nitroxyalkylamide derivatives
  申请人：Sankyo Company, Limited

  公开号：US05580893A1

  公开（公告）日：1996-12-03

  Nitroxyalkylamide compounds having the formula: R.sup.1 --(A).sub.n --CONH--B'--ONO.sub.2 wherein R.sup.1 is an optionally substituted furyl, furyloxy, thienyl, thienyloxy, isoxazolyl, phenoxy, phenylthio or 1,4-dibenzodioxanyl, A is a C.sub.1 -C.sub.4 alkylene group; B' is a C.sub.1 -C.sub.4 alkylene group; and n is 0 or 1. The compounds of the present invention have a desirable vasodilator action for collateral vessels and an anti-anginal action, and are useful as therapeutic agents for treating angina pectoris.

  具有以下公式的Nitroxyalkylamide化合物：R.sup.1--(A).sub.n--CONH--B'--ONO.sub.2，其中R.sup.1是可选择取代的呋喃基，呋喃氧基，噻吩基，噻吩氧基，异噁唑基，苯氧基，苯基硫或1,4-二苯并二氧杂环基，A是C.sub.1-C.sub.4烷基；B'是C.sub.1-C.sub.4烷基；n为0或1。本发明的化合物具有适合于侧支血管的血管扩张作用和抗心绞痛作用，并且可用作治疗心绞痛的治疗剂。