(+/-)-4,4-dimethyl-3-phenylpentanoic acid | 83867-96-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (+/-)-4,4-dimethyl-3-phenylpentanoic acid
• 英文别名: 4,4-dimethyl-3-phenylpentanoic acid；4,4-dimethyl-3-phenyl-valeric acid；4,4-Dimethyl-3-phenyl-valeriansaeure
• CAS: 83867-96-3
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: VFPUWNPGVKAJNC-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  308.4±11.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (+/-)-4,4-dimethyl-3-phenylpentanoic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (+)-(R)-4,4-dimethyl-3-phenylpentan-1-ol
  参考文献：
  名称：

  Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol

  摘要：

  Enantio selective acylation of some(+/-)-3-alkyl-3-phenyl-1-propanols was performed with enzymes as catalysts. Moderate enantiomeric ratios (E), ranging up to E = 11.6, were obtained. In the resolution, some of the lipases selectively acylated the (+)-enantiomer while others acylated the (-)-enantiomer of the gamma-substituted primary alcohols 1-4. Thus, it is possible to obtain both enantiomers of the alcohols as remaining substrate with high enantiomeric purity. The resolution of (+/-)-4,4-dimethyl-3-phenyl-1-pentanol 4 was extensively studied and screening experiments were conducted to select suitable lipase(s), reaction medium, acyl donor and appropriate temperature combinations to increase the enantiomeric ratio. Chirazyme (R) L-6/chloroform/vinyl propionate/38 degrees C and Chirazyme (R) L-7/di-iso-propyl ether/vinyl propionate/0 degrees C were chosen to obtain both enantiomers, (R)-(+)-4 and (S)-(-)-4, respectively, via sequential resolutions in excellent enantiomeric excess (> 98%) and in 25% and 22% yield, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.002
• 作为产物：
  描述：

  2,2,2-三甲基苯乙酮 在 sodium amalgam 、 乙醇 、 potassium carbonate 、 乙酰氯 、 锌 、 苯 作用下， 生成 (+/-)-4,4-dimethyl-3-phenylpentanoic acid
  参考文献：
  名称：

  Data extraction from the web based on pre-defined schema

  摘要：

  With the development of the Internet, the World Wide Web has become an invaluable information source for most organizations. However, most documents available from the Web are in HTML form which is originally designed for document formatting with little consideration of its contents. Effectively extracting data from such documents remains a non-trivial task. In this paper, we present a schema-guided approach to extracting data from HTML pages. Under the approach, the user defines a schema specifying what to be extracted and provides sample mappings between the schema and the HTML page. The system will induce the mapping rules and generate a wrapper that takes the HTML page as input and produces the required data in the form of XML conforming to the user-defined schema. A prototype system implementing the approach has been developed. The preliminary experiments indicate that the proposed semi-automatic approach is not only easy to use but also able to produce a wrapper that extracts required data from inputted pages with high accuracy.

  DOI：

  10.1007/bf02943278

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。
• Colorant compounds
  申请人：Banning H. Jeffrey

  公开号：US20060020141A1

  公开（公告）日：2006-01-26

  Compounds of the formula wherein M is either (1) a metal ion having a positive charge of +y wherein y is an integer which is at least 2, said metal ion being capable of forming a compound with at least two chromogen moieties, or (2) a metal-containing moiety capable of forming a compound with at least two chromogen moieties, z is an integer representing the number of chromogen moieties associated with the metal and is at least 2, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a, b, c, d, Y, and z are as defined herein, Q − is a COO − group or a SO 3 — group, A is an organic anion, and CA is either a hydrogen atom or a cation associated with all but one of the Q − groups.

  式中的化合物，其中M是一个带有正电荷+y的金属离子，其中y是至少为2的整数，该金属离子能够与至少两个色团基团形成化合物，或者M是一个含金属基团的基团，能够与至少两个色团基团形成化合物，z是表示与金属相关的色团基团数量的整数，至少为2，R1、R2、R3、R4、R5、R6、R7、a、b、c、d、Y和z的定义如上所述，Q-是一个COO-基团或SO3-基团，A是一个有机阴离子，CA是一个氢原子或与除一个Q-基团之外的所有Q-基团相关联的阳离子。
• On the mechanism of the addition of organolithium reagents to cinnamic acids
  作者：Marı́a José Aurell、Marı́a José Bañuls、Ramon Mestres、Elena Muñoz

  DOI：10.1016/s0040-4020(00)01096-6

  日期：2001.2

  regioselectivity of the addition of tert-butyllithium to cinnamic acid is subject to reaction conditions and to substituent electronic effects. Significant effects are observed in the presence of several additives including a radical trap such as α-methylstyrene. Competition experiments by addition of the organolithium reagent to mixtures of substituted cinnamic acids show that the relative rates of both

  向肉桂酸添加叔丁基锂的区域选择性受反应条件和取代基电子效应的影响。在几种添加剂的存在下观察到了显着的效果，其中包括自由基陷阱，例如α-甲基苯乙烯。通过向取代的肉桂酸混合物中添加有机锂试剂进行竞争实验表明，起始酸的转化率和1,3-加合物的形成的相对速率均受电子效应的影响，而1,4-加成的速率则受到电子效应的影响。不依赖于取代基。这些特征与极性加成机理相一致，但是也可以实现快速SET平衡，然后进行缓慢的自由基结合。
• Addition of organolithium reagents to cinnamic acids
  作者：María José Aurell、María José Bañuls、Ramon Mestres、Elena Muñoz

  DOI：10.1016/s0040-4020(98)01074-6

  日期：1999.1

  Reaction of tert-butyllithium with p- and m-substituted cinnamic acids at low temperature affords mixtures of 1,4- and 1,3-addition products, whose composition depend on the nature of the substituents. Electron-donating and electron-withdrawing groups favour 1,4- and 1,3-additions, respectively. Linear correlations are obtained with electronic effect and with radical substituent constants.

  的反应叔与丁基锂p -和米处的1,4-和1,3-加成产物，其组成依赖于取代基的性质低温，得到的混合物取代的肉桂酸。给电子基团和吸电子基团分别有利于1，4-和1，3-加成。线性相关通过电子效应和自由基取代基常数获得。
• Excellent stereocontrol in intramolecular Buchner cyclisations and subsequent cycloadditions; stereospecific construction of polycyclic systems
  作者：Anita R. Maguire、N. Rachael Buckley、Patrick O'Leary、George Ferguson

  DOI：10.1039/cc9960002595

  日期：——

  Highly diastereoselective rhodium(II) acetate-catalysed intramolecular addition of α-diazo ketones to aromatic rings to form the azulenones 3 has been achieved; the norcaradiene form of 3 undergoes efficient stereospecific cycloaddition with phenyltriazolinedione, in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case.

  已实现高非对映选择性的醋酸铑(II)催化α-重氮酮分子内加成到芳环形成并环庚烯酮3;3的降降萘二烯形式与苯基三唑烷二酮进行高效的立体专一性环加成,无论是分步还是串联过程,都能得到单一非对映异构体的五环系统4。