D-扁桃酸钠盐 | 54385-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: D-扁桃酸钠盐
• 英文名称: sodium D-mandelate
• 英文别名: Benzeneacetic acid, alpha-hydroxy-, monosodium salt, (alphaR)-；sodium;(2R)-2-hydroxy-2-phenylacetate
• CAS: 54385-47-6
• 化学式: C₈H₇O₃*Na
• 分子量: 174.132
• InChiKey: FWDLHTBMGQEUDU-OGFXRTJISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.53
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  D-扁桃酸钠盐 在 三羟甲基氨基甲烷盐酸盐 、 nicotinamide adenine dinucleotide 作用下， 以 水 为溶剂， 生成 苯基乙醛酸钠
  参考文献：
  名称：

  A New Family ofD-2-Hydroxyacid Dehydrogenases That ComprisesD-Mandelate Dehydrogenases and 2-Ketopantoate Reductases

  摘要：

  通过活性染色程序和PCR分离粪肠球菌IAM10071的d-扁桃酸脱氢酶(d-ManDH)基因，并在大肠杆菌细胞中表达。该重组酶对各种具有大量疏水侧链的2-酮酸底物，特别是C3支链底物，如苯甲酰甲酸和2-酮异戊酸，表现出高催化活性，并对NADH和NAD+表现出严格的辅酶特异性。它与已知的 NADP 依赖性 2-酮泛解酸还原酶 (KPR) 显示出显着的序列相似性。这些结果表明，d-ManDH 与 KPR 一起构成了一个新的 d-2-羟基酸脱氢酶家族，其作用于 C3 支链 2-酮酸底物，对辅酶和底物具有各种特异性。

  DOI：

  10.1271/bbb.70827
• 作为产物：
  描述：

  顺式-(1S,4S)-N-甲基-4-(3,4-二氯苯基)-1,2,3,4-四氢-1-萘胺扁桃酸盐 在 sodium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 生成 D-扁桃酸钠盐
  参考文献：
  名称：

  A Low-Waste Process To Sertraline By Diastereomeric Crystal Resolution and Waste Isomer Racemisation

  摘要：

  A semi-continuous method for recovering waste sertraline isomers from a diastereomeric crystallisation process is described in which the mother liquors from a highly selective mandelic acid resolution for the (1S,4S) isomer are treated sequentially with SCRAM, an iridium-based chiral amine racemisation catalyst, and then catalytic potassium tertiary butoxide to epimerise the methine chiral centre. The green, low-waste process also deals with recovery and recycle of the precious-metal catalyst, providing both good economics and high-quality product.

  DOI：

  10.1021/op900112f
• 作为试剂：
  描述：

  苯乙酮 在 10% Ru/C 、 氢气 、 D-扁桃酸钠盐 作用下， 以 乙醇 为溶剂， 生成 苏合香醇
  参考文献：
  名称：

  Chirality transfer in mandelate ionic liquids through ion pairing effects

  摘要：

  Ion pairing in [N-(3'-oxohexyl)-N-methylimidazolium][(R)-mandelate] was probed as a function of its concentration in ethanol and compared to the corresponding [(S)-camphorsulfonate] ionic liquid. The applied methodologies comprised asymmetric hydrogenation with ee monitoring as well as independent diffusion-ordered NMR and conductivity measurements. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.018

文献信息

• Selective hydrogenation of arenes to cyclohexanes in water catalyzed by chitin-supported ruthenium nanoparticles
  作者：Yuna Morioka、Aki Matsuoka、Kellie Binder、Benjamin R. Knappett、Andrew E. H. Wheatley、Hiroshi Naka

  DOI：10.1039/c6cy00899b

  日期：——

  The selective hydrogenation of aromatic compounds to cyclohexanes was found to be promoted by chitin-supported ruthenium nanoparticles (Ru/chitin) under near-neutral, aqueous conditions without the loss of C–O/C–N linkages at benzylic positions.

  发现在近中性的水性条件下，几丁质负载的钌纳米粒子（Ru /几丁质）可促进芳香族化合物选择性氢化成环己烷，而不会失去苄基位置的C–O / C–N键。
• Structure‐cytotoxicity relationship for apoptotic inducers organotin(IV) derivatives of mandelic acid and L‐proline and their mixed ligand complexes having enhanced cytotoxicity
  作者：Mala Nath、Partha Roy、Rutusmita Mishra、Mridula Thakur

  DOI：10.1002/aoc.4663

  日期：——

  Structure‐cytotoxicity relationship of di−/tri‐organotin(IV) derivatives of mandelic acid (1–4), L‐proline (5–7, 15, 16), and mixed ligand complexes of latter with 1,10‐phenanthroline (8–14) investigated on the basis of MTT assay against human cancer cell lines, viz. MCF‐7 (mammary cancer), HepG2 (liver cancer) and PC‐3 (prostate cancer) in vitro indicated that all complexes except methyl‐ and octyl‐

  结构的细胞毒性二- /三-有机锡（IV）的关系扁桃酸（的衍生物1 - 4），L-脯氨酸（5 - 7，15，16）中，用1,10-菲咯啉的后者的混合配体络合物（8 - 14）研究了MTT测定对人癌细胞系，的基础上即。体外MCF-7（乳腺癌），HepG2（肝癌）和PC-3（前列腺癌）表明，除甲基和辛基类似物外，所有复合物均具有潜在的细胞毒性。活性最高的是扁桃酸二丁基锡（IV）（2），显示IC 50对MCF‐7，HepG2和PC‐3分别为2.03±0.40、0.98±0.23和3.86±1.68μM，对MCF‐7分别为≈15和2.5倍，对HepG2为20和5倍，对HepG2为5和≈3倍PC-3的细胞毒性分别比顺铂和5-氟尿嘧啶高。扁桃酸的二有机锡（IV）衍生物比三有机锡类似物更具细胞毒性。L-脯氨酸的有机锡（IV）衍生物（Bu 3 Sn（Pro）16除外）的细胞毒性比扁桃酸的细胞毒性小，但与1,
• Concise Synthesis of Key Intermediate of Mirabegron via a Mixed Anhydride Method
  作者：Qi-Long Zhang、Zhi-Yuan Zhuang、Qing-Dong Liu、Zhan-Ming Zhang、Fu-Xu Zhan、Geng-Xiu Zheng

  DOI：10.1021/acs.oprd.6b00231

  日期：2016.11.18

  An efficiently scalable synthesis of key intermediate toward mirabegron has been developed via a mixed anhydride method, employing PivCl instead of EDCI and HOBt. The developed process produced (R)-2-hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide (10) in 91.5–92.3% yield and >99.0% HPLC purity under mild conditions. During this process, a side reaction induced by triethylamine hydrochloride was discovered

  通过混合酸酐法，采用PivCl代替EDCI和HOBt，开发了一种有效的可扩展规模的米拉贝隆关键中间体合成方法。发达的方法在温和的条件下以91.5–92.3％的收率和> 99.0％的HPLC纯度生产了（R）-2-羟基-N-（4-硝基苯乙基）-2-苯基乙酰胺（10）。在此过程中，发现并研究了由三乙胺盐酸盐引起的副反应，最终通过在双相溶剂体系中进行反应避免了这一副反应。
• [EN] ENANTIOSPECIFIC PROCESS FOR THE PREPARATION OF PAROXETINE INTERMEDIATE<br/>[FR] PROCEDE ENANTIOSPECIFIQUE PERMETTANT DE PREPARER UN INTERMEDIAIRE DE PAROXETINE
  申请人：NATCO PHARMA LTD

  公开号：WO2005063707A1

  公开（公告）日：2005-07-14

  A novel, improved, and enantiospecific process for the preparation of (-)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine of formula-(I), an advanced intermediate in the manufacture of antidepressant drug paroxetine is disclosed in the present invention. Compound of formula-(XXII) is prepared by resolution of compound of formula-(XX) using a chiral acid followed by hydrogenation of the resolved amine. Michael addition of the compound of formula-(XXII) onto acrylate esters gave the compounds of formula-(XXIII). Conversion of the hydroxy group present in compound of formula-(XXIII) into a leaving group followed by treatment with a strong base gave the enantiospecific intramolecularly cyclized piperidine derivative of formula-(XXV). Reduction of the ester group present in compound of formula-(XXV) with a metal hydride reducing agent gave the compound of formula-I with more than 97% chiral purity. Further purification of compound of formula-I to >99.5% is achieved by one recrystallization from a number of solvents. Present process is easily adaptable for commercial preparation of (-)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine of formula-(I).

  本发明揭示了一种用于制备抗抑郁药帕罗西汀的先进中间体(-)-反式-4-(4-氟苯基)-3-羟甲基-1-甲基哌啶的改进和对映具体过程。通过使用手性酸对化合物XX进行拆分，然后对已拆分的胺进行氢化，制备了化合物XXII的方法。将化合物XXII与丙烯酸酯发生迈克尔加成反应，得到了化合物XXIII。将化合物XXIII中的羟基转化为一个脱离基，然后经过强碱处理，得到了对映具体的分子内环化哌啶衍生物XXV。将化合物XXV中的酯基还原为金属氢化物还原剂，得到了具有超过97%对映纯度的化合物I。通过在多种溶剂中进行一次结晶，将化合物I进一步纯化至>99.5%。本过程易于用于商业制备(-)-反式-4-(4-氟苯基)-3-羟甲基-1-甲基哌啶的方法。
• An efficient and versatile synthesis of piperazine-2-carboxamides
  作者：K. Rossen、J. Sager、L.M. DiMichele

  DOI：10.1016/s0040-4039(97)00607-2

  日期：1997.5

  An efficient and versatile synthesis of piperazine-2-carboxamides 5 is described. The preparation consists of a one-pot, 4-component Ugi condensation between an N-alkylethylenediamine 1, chloroacetaldehyde (2), an isonitrile 3 and a carboxylic acid 4.

  描述了哌嗪-2-羧酰胺5的有效且通用的合成。该制剂由N-烷基乙二胺1，氯乙醛（2），异腈3和羧酸4之间的一锅四组分Ugi缩合组成。