3-phenylpropionate | 826-17-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-phenylpropionate
• 英文别名: hydrocinnamic acid；hydrocinnamate；3-phenyl-propionate；3-phenylpropanoate
• CAS: 826-17-5
• 化学式: C₉H₉O₂
• 分子量: 149.169
• InChiKey: XMIIGOLPHOKFCH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 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：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylpropionate 生成 spiro<2,5>octadienyl anion
  参考文献：
  名称：

  On the generation and characterization of the spiro[2,5]octadienyl anion in the gas phase

  摘要：

  AbstractThree routes have been explored in both a high‐pressure chemical ionization (CI) source and a low‐pressure Fourier transform ion cyclotron resonance (FT‐ICR) cell to generate the spiro[2,5]octadienyl anion in the gas phase: (i) proton abstraction from spiro[2,5]octa‐4,6‐diene; (ii) expulsion of trimethysilyl fluoride by phenyl ring participation following fluoride anion attack upon the silicon centre of 2‐phenylethyl trimethylsilane; and (iii) collisionally induced dissociation (CID) of the carboxylate anion of 3‐phenylpropanoic acid via carbon dioxide loss. From comparison of the CID spectra of various reference [C8H9]− ions with those of the [C8H9]− ions which could be generated via the routes (i) and (iii) in the CI source it can be concluded that only the third route yields a [C8H9]−ion whose CID spectrum is not inconsistent with the one expected for the spiro[2,5]octadienyl anion. In the FT‐ICR cell [C8H9]− ions are generated along all three routes; their structures have been identified by specific ion‐molecule reactions and appear to be different. Route (i) yields an α‐methyl benzyl anion, probably due to isomerization within the ion‐molecule complex formed. An ortho‐ethylphenyl anion is formed along route (ii), presumably due to an intramolecular ortho proton abstraction in the generated trimethylsilyl fluoride solvated 2‐phenylethyl primary carbanion. The [C8H9]− ion formed along route (iii) shows reactions similar to those of the 1,1‐dimethylcyclohexadienyl anion which is structurally related to the spiro[2,5]octadienyl anion. Furthermore, the [C8H9]− ion generated via route (iii) reacts with hexafluorobenzene under expulsion of only one hydrogen fluoride molecule which contains exclusively one of the original phenyl ring hydrogen atoms. On the basis of all these observations it is therefore quite likely that the spiro[2,5]octadienyl anion is formed by collisionally induced decarboxylation of the 3‐phenylpropanoic acid carboxylate anion and can be a long‐lived and stable species in the gas phase.

  DOI：

  10.1002/oms.1210240807
• 作为产物：
  描述：

  cinnamate ion 在 ruthenium(II) tris(4,4'-dimethyl-2,2'-bipyridine) 、 sodium dodecyl-sulfate 、 ascorbate 作用下， 以 水 为溶剂， 反应 14.0h， 以95%的产率得到3-phenylpropionate
  参考文献：
  名称：

  具有绿色发光二极管的水合电子制备量可承受的三元化三（联吡啶）钌催化剂

  摘要：

  我们已经研究了配体的烷基取代，以改善光氧化还原催化系统中标题配合物的性能，该系统通过光子池产生合成可用量的水合电子。尽管产生了超级还原剂，但这些电子源仅消耗生物可利用的抗坏血酸，并由绿色发光二极管（LED）驱动。取代通过淬灭参数的相互作用，还原的催化剂OER和胶束-水界面上的抗坏血酸基团的重组率以及OER光电离的量子产率之间的相互作用来影响催化剂的活性。激光闪光光解法可提供有关所有这些过程的全面信息，并可以定量预测在LED动力学中观察到的活性，但是后一种方法提供了在合成时间范围内在光照下催化剂稳定性的唯一途径。具有二甲基联吡啶配体的均溶络合物作为最佳组合出现，其相对于母体化合物具有两倍高的活性和不减的稳定性。通过这种复合物，我们实现了烷基和芳基氯化物和氟化物的脱卤，碳-碳双键的氢化以及自偶联反应和交叉偶联反应。所用的所有基材都不能透过普通的光氧化还原催化剂，但作为超级还原剂的水合电子没有任

  DOI：

  10.1002/chem.201801955

文献信息

• Selective Enzymatic Transformation to Aldehydes<i>in vivo</i>by Fungal Carboxylate Reductase from<i>Neurospora crassa</i>
  作者：Daniel Schwendenwein、Giuseppe Fiume、Hansjörg Weber、Florian Rudroff、Margit Winkler

  DOI：10.1002/adsc.201600914

  日期：2016.11.3

  with only a handful of biocatalysts available to this end. We have increased the spectrum of carboxylate-reducing enzymes (CARs) with the sequence of a fungal CAR from Neurospora crassa OR74A (NcCAR). NcCAR was efficiently expressed in E. coli using an autoinduction protocol at low temperature. It was purified and characterized in vitro, revealing a broad substrate acceptance, a pH optimum at pH 5.5-6

  羧酸的酶促还原还处于初期，只有少数几种生物催化剂可用于此目的。我们已经利用来自神经孢霉OR74A（NcCAR）的真菌CAR的序列增加了羧酸盐还原酶（CARs）的谱图。NcCAR在低温下使用自动诱导方案在大肠杆菌中有效表达。对其进行了纯化和体外表征，显示了广泛的底物接受性，最适pH值为5.5-6.0，Tm为45°C和副产物焦磷酸盐的抑制作用（可通过添加焦磷酸酶来缓解）。NcCAR的合成效用已在使用大肠杆菌K-12 MG1655 RARE菌株进行全细胞生物转化中得到证实，目的是抑制过度还原为不想要的酒精。由戊酸（30 mM）以克规模制备芳香化合物胡椒醛，分离出的产率为92％，纯度> 98％。这对应于1.5g / L / h的生产率。
• A chiral spirobifluorene-based bis(salen) zinc(<scp>ii</scp>) receptor towards highly enantioselective binding of chiral carboxylates
  作者：Sk Asif Ikbal、Yoko Sakata、Shigehisa Akine

  DOI：10.1039/d1dt00218j

  日期：——

  We have designed a new chiral receptor based on two salen zinc(II) complex units connected with a spirobifluorene framework. The chiral receptor is proven to enantioselectively bind chiral carboxylate guests and the differences between the binding constants of enantiomeric guests were up to more than one order of magnitude.

  我们设计了一种新的手性受体，它基于两个与螺二芴骨架相连的Salen锌（II）复杂单元。已证明手性受体能对映选择性地结合手性羧酸盐客体，并且对映体客体的结合常数之间的差异高达一个以上的数量级。
• ——
  作者：Barbara R. Sharak Genthner

  DOI：10.1023/a:1008348123672

  日期：——

  consortia. Selected characteristics of ortho reductive dehalogenation were examined in consortia developed from the highest actively dechlorinating dilutions of the original 2CB consortia, designated consortia M34(-9), P20(-9), P21(-9) and M50(-7). In addition to 2-chlorobenzoate, all four dilution consortia dehalogenated 4 of 32 additional halogenated aromatic substrates tested, including 2-bromobenzoate;

  脱氯是4个2-氯苯甲酸酯降解产甲烷菌群中2CB生物降解的第一步。在最初的2CB联合体的最高活性脱氯稀释液（称为联合体M34（-9），P20（-9），P21（-9）和M50（-7））开发的联合体中，检查了原位还原脱卤的选定特征。除2-氯苯甲酸酯外，所有四个稀释协会对32种测试的其他卤代芳族底物中的4种进行了脱卤处理，其中包括2-溴苯甲酸酯；2,6-二氯苯甲酸酯; 2,4-二氯苯甲酸酯; 和2-氯-5-羟基苯甲酸酯。脱卤仅发生在邻位。从2，6-二氯苯甲酸酯中除去两种邻氯。从2-溴苯甲酸酯和2,6-二氯苯甲酸酯中检出苯甲酸酯。由2形成4-氯苯甲酸酯和3-羟基苯甲酸酯 4-二氯苯甲酸酯和2-氯-5-羟基苯甲酸酯 只有苯甲酸酯被进一步降解。稍微改变母体“苯甲酸酯分子”的结构导致观察到除脱卤以外的还原性生物转化。所有四个财团将2-氯苯甲醛还原为2-氯苄醇。2-氯茴香醚被四个财团中的三个进行O-脱甲氧基
• Process to prepare amino carboxylic acid salts
  申请人：Monsanto Company

  公开号：US05367112A1

  公开（公告）日：1994-11-22

  An improved process is disclosed to prepare an carboxylic acid salt. According to the process, an aqueous solution of an alcohol is contacted with an alkali metal hydroxide in the presence of an effective amount of a copper catalyst that contains from about 50 parts per million to about 10,000 parts per million of an element selected from the group consisting of chromium, titanium, niobium, tantalum, zirconium, vanadium, molybdenum, manganese, tungsten, cobalt, nickel and mixtures thereof. Raney copper is preferred.

  本发明揭示了一种改进的制备羧酸盐的工艺。根据该工艺，将一种醇的水溶液与一种碱金属氢氧化物在存在有效量的含有从约50ppm到约10,000ppm的铬、钛、铌、钽、锆、钒、钼、锰、钨、钴、镍和其混合物中所选元素的铜催化剂的情况下接触。Raney铜是首选。
• Characterization of the <i>hca</i> Cluster Encoding the Dioxygenolytic Pathway for Initial Catabolism of 3-Phenylpropionic Acid in <i>Escherichia coli</i> K-12
  作者：Eduardo Díaz、Abel Ferrández、José L. García

  DOI：10.1128/jb.180.11.2915-2923.1998

  日期：1998.6

  We have identified, cloned, and sequenced the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid (PP) in Escherichia coli K-12. This cluster maps at min 57.5 of the chromosome and is composed of five catabolic genes arranged as a putative operon ( hcaA1A2CBD ) and two additional genes transcribed in the opposite direction that encode a potential permease ( hcaT ) and a regulator ( hcaR ). Sequence comparisons revealed that while hcaA1A2CD genes encode the four subunits of the 3-phenylpropionate dioxygenase, the hcaB gene codes for the corresponding cis -dihydrodiol dehydrogenase. This type of catabolic module is homologous to those encoding class IIB dioxygenases and becomes the first example of such a catabolic cluster in E. coli . The inducible expression of the hca genes requires the presence of the hcaR gene product, which acts as a transcriptional activator and shows significant sequence similarity to members of the LysR family of regulators. Interestingly, the HcaA1A2CD and HcaB enzymes are able to oxidize not only PP to 3-(2,3-dihydroxyphenyl)propionate (DHPP) but also cinnamic acid (CI) to its corresponding 2,3-dihydroxy derivative. Further catabolism of DHPP requires the mhp -encoded meta fission pathway for the mineralization of 3-hydroxyphenylpropionate (3HPP) (A. Ferrández, J. L. Garcı́a, and E. Dı́az, J. Bacteriol. 179:2573–2581, 1997). Expression in Salmonella typhimurium of the mhp genes alone or in combination with the hca cluster allowed the growth of the recombinant bacteria in 3-hydroxycinnamic acid (3HCI) and CI, respectively. Thus, the convergent mhp - and hca -encoded pathways are also functional in S. typhimurium , and they are responsible for the catabolism of different phenylpropanoid compounds (3HPP, 3HCI, PP, and CI) widely available in nature.

  摘要 我们鉴定、克隆并测序了 hca 簇，该簇编码大肠杆菌中 3-苯基丙酸（PP）初始分解的二氧分解途径。 大肠杆菌 K-12.该基因簇位于染色体的第 57.5 小节，由五个分解基因组成，这些基因组成了一个假定操作子（hcaA1A2CBD）。 hcaA1A2CBD ) 和另外两个反向转录的基因，这两个基因编码一种潜在的渗透酶 ( hcaT )和一个调节器( hcaR ).序列比较显示 hcaA1A2CD 基因编码 3-苯基丙酸二氧合酶的四个亚基，而 hcaB 基因编码相应的 顺式 -二氢二醇脱氢酶。这种分解模块与编码 IIB 类二加氧酶的模块同源，是大肠杆菌中第一个此类分解簇的实例。 大肠杆菌 .诱导表达 hca 基因的诱导表达需要 hcaR 基因产物，它是一种转录激活因子，与 LysR 家族的调节因子序列非常相似。有趣的是，HcaA1A2CD 和 HcaB 酶不仅能将 PP 氧化成 3-（2,3-二羟基苯基）丙酸（DHPP），还能将肉桂酸（CI）氧化成其相应的 2,3- 二羟基衍生物。DHPP 的进一步分解需要 mhp -编码的 元 Ferrández, J. L. Garcı́a, and E. Dı́az, J. Bacteriol.179:2573-2581, 1997).在 鼠伤寒沙门氏菌 的 mhp 基因单独或与 hca 簇的重组细菌可分别在 3-羟基肉桂酸（3HCI）和 CI 中生长。因此，趋同的 mhp - 和 hca -编码的途径在 鼠伤寒杆菌 它们负责分解自然界中广泛存在的不同苯丙类化合物（3HPP、3HCI、PP 和 CI）。