(R)-4-methyl-3-phenylpentanoic acid | 22573-54-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-4-methyl-3-phenylpentanoic acid
• 英文别名: (3R)-4-methyl-3-phenylpentanoic acid
• CAS: 22573-54-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: QTSNMZCWXXMRTK-LLVKDONJSA-N

物化性质

• 沸点：
  298.3±9.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-methyl-3-phenylpentanoic acid 在 三氯化铝 、 草酰氯 作用下， 生成 (R)-3-Isopropyl-indan-1-one
  参考文献：
  名称：

  Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

  摘要：

  Chiral beta-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3-alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.

  DOI：

  10.1016/s0957-4166(00)80481-4
• 作为产物：
  描述：

  (E)-(4S,5R)-4-benzyl-3-(3'-phenyl-2'-propenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 在 氧气 lithium hydroxide 、 三乙基硼 、 双氧水 、 三正丁基氢锡 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (R)-4-methyl-3-phenylpentanoic acid
  参考文献：
  名称：

  Stereoselective Conjugate Radical Additions:  Application of a Fluorous Oxazolidinone Chiral Auxiliary for Efficient Tin Removal

  摘要：

  A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazoldinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.

  DOI：

  10.1021/ol050956k

文献信息

• Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst
  作者：Declan P. Gavin、Edel J. Murphy、Aoife M. Foley、Ignacio Abreu Castilla、F. Jerry Reen、David F. Woods、Stuart G. Collins、Fergal O'Gara、Anita R. Maguire

  DOI：10.1002/adsc.201801691

  日期：2019.6.6

  Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents

  描述了评估从海洋宏基因组库中分离为26D的酯酶的方法。发现酯酶26D具有独特的底物范围，包括使用市售酶不易以合成有用的方式实现的合成转化。酯酶26D是更具选择性的朝向具有较大的，更空间要求的取代基的底物（即，异-丙基或叔-丁基基团）上的β碳，这是相对于其中显示的偏好基板与空间位先前测试的市售的酶β-碳原子上的取代基（例如甲基）要求较低。
• Enantioselective Conjugate Radical Addition to α‘-Hydroxy Enones
  作者：Sunggi Lee、Chae Jo Lim、Sunggak Kim、Rajesh Subramaniam、Jake Zimmerman、Mukund P. Sibi

  DOI：10.1021/ol061634z

  日期：2006.9

  Enantioselective conjugate radical addition to alpha'-hydroxy alpha,beta-unsaturated ketones, compounds containing bidentate donors, has been investigated. It has been found that radical additions to alpha'-hydroxy alpha,beta-unsaturated ketones in the presence of Mg(NTf2)2 and bisoxazoline ligand 5a proceeded cleanly, yielding the addition products in high chemical yields and good enantiomeric excesses

  已研究了向α'-羟基α，β-不饱和酮（含双齿供体的化合物）的对映选择性共轭基团的加成反应。已经发现，在Mg（NTf2）2和双恶唑啉配体5a存在下，向α′-羟基α，β-不饱和酮的自由基加成反应干净进行，以高化学产率和良好的对映体过量产生加成产物。
• A Non-Iterative Direct Displacement-Based Design Procedure for SDOF Steel Columns: Using Substitute Structure
  作者：Y.-Y. Lin、K.-C. Chang

  DOI：10.1017/s1727719100003208

  日期：2003.9

  Traditionally, the yield displacement of a nonlinear structure was calculated by using the direct displacement-based seismic design method which usually requires a repeatedly iterative procedure no matter whether the substitute structure or inelastic design spectra has been adopted in the procedure. This will sometimes result in inefficiency if too many iterative cycles need to be produced in a design case for convergency. To avoid this disadvantage, this paper presents a non-iterative direct displacement-based design procedure for SDOF steel columns using the substitute structure approach. By combining the yielding property with the stiffness property of the designed steel columns, the procedure can immediately obtain the column's cross-section via the chosen target displacement and ductility ratio.

  Abstract 传统上，非线性结构的屈服位移是通过直接基于位移的抗震设计方法来计算的，这种方法通常需要反复的迭代程序，无论程序中是否采用了替代结构或非弹性设计谱。如果在一个设计案例中需要产生过多的迭代循环以达到收敛，这有时会导致效率低下。为避免这一弊端，本文提出了一种使用替代结构方法的基于位移的 SDOF 钢柱非迭代直接设计程序。通过将屈服特性与设计钢柱的刚度特性相结合，该程序可以通过所选的目标位移和延性比立即获得钢柱的截面。
• Asymmetric Michael additions of Grignard reagents to cinnamamides deriving from N-alkyl (R)-(−)-2-aminobutan-1-ol
  作者：Joe¨l Touet、Sylvie Baudouin、Eric Brown

  DOI：10.1016/s0957-4166(00)82287-9

  日期：1992.5

  Reaction of cinnamoyl chloride with various N-alkyl derivatives of (R)-(−)-2-aminobutan-1-ol (a readily available reagent) afforded the corresponding cinnamamides. Michael additions of Grignard reagents to the latter, followed by acidic hydrolysis, yielded optically active β-phenylalkanoic acids whose ee most generally were in the range 72–100%.

  肉桂酰氯与（R）-（-）-2-氨基丁丹-1-醇的各种N-烷基衍生物（一种容易获得的试剂）反应，得到相应的肉桂酰胺。在后者的Michael加Grignard试剂后，进行酸水解，得到旋光性的β-苯基链烷酸，其ee最普遍在72-100％的范围内。
• Asymmetric syntheses and bio-evaluation of novel chiral esters derived from substituted tetrafluorobenzyl alcohol
  作者：Shengzhen Xu、Huangyong Li、Xiaohui Wang、Changshui Chen、Minhui Cao、Xiufang Cao

  DOI：10.1016/j.bmcl.2014.04.055

  日期：2014.6

  A series of novel chiral esters derived from tetrafluorobenzyl alcohol were designed and prepared via asymmetric synthesis. The target molecules have been identified on the basis of analytical spectra data. All newly synthesized compounds have been screened their potential insecticidal activity against Plutella xylostella compared with those of fenvalerate and d-trans-phenothrin by standard method

  通过不对称合成设计并制备了一系列衍生自四氟苄醇的新型手性酯。根据分析光谱数据确定了目标分子。已通过标准方法筛选了所有新合成的化合物对小菜蛾小菜蛾的潜在杀虫活性（与苯丙戊酸酯和d-反式-邻苯二酚相比），以及各对对映异构体（3 - B1 - R / S，3 - C1 - R / S，3 - D1 - R /S）表示明显不同的活动。