(R)-3,4-diphenyl butanoic acid | 6995-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-3,4-diphenyl butanoic acid
• 英文别名: 3.4-Diphenyl-buttersaeure；(3R)-3,4-diphenylbutanoic acid
• CAS: 6995-48-8
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: JOBZTAYSABJDKN-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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)-3,4-diphenyl butanoic acid 、 1-氨基-3,5-二甲苯 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (R)-N-(3,5-Dimethyl-phenyl)-3,4-diphenyl-butyramide
  参考文献：
  名称：

  Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions

  摘要：

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.

  DOI：

  10.1021/jo952223r
• 作为产物：
  描述：

  N-(3-phenylpropanoyl)-(S)-1-phenylethylamine 在 盐酸 、 氢氧化钾 、 四甲基乙二胺 、 仲丁基锂 作用下， 反应 8.5h， 生成 (R)-3,4-diphenyl butanoic acid
  参考文献：
  名称：

  复杂物诱导的邻近效应：在手性辅助介导的β-取代的二级羧酰胺的β-锂取代序列中的立体选择性碳-碳键形成。

  摘要：

  DOI：

  10.1021/jo972042k

文献信息

• 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。
• Palladium-Catalyzed Enantioselective Redox-Relay Heck Arylation of 1,1-Disubstituted Homoallylic Alcohols
  作者：Zhi-Min Chen、Margaret J. Hilton、Matthew S. Sigman

  DOI：10.1021/jacs.6b06994

  日期：2016.9.14

  An enantioselective redox-relay oxidative Heck arylation of 1,1-disubstituted alkenes to construct β-stereocenters was developed using a new pyridyl-oxazoline ligand. Various 1,2-diaryl carbonyl compounds were readily obtained in moderate yield and good to excellent enantioselectivity. Additionally, analysis of the reaction outcomes using multidimensional correlations revealed that enantioselectivity

  使用新的吡啶基恶唑啉配体开发了 1,​​1-二取代烯烃的对映选择性氧化还原中继氧化 Heck 芳基化以构建 β-立构中心。各种 1,2-二芳基羰基化合物很容易以中等收率和良好至优异的对映选择性获得。此外，使用多维相关性对反应结果的分析表明，对映选择性与 1,1-二取代烯醇的特定电子特征和配体的极化程度有关。
• Regio-, stereo-, and enantioselectivity in the electrophilic reactions of 2-amino-4-phenyl-3-butenenitriles
  作者：Chih Jung Chang、Jim Min Fang、Li Fan Liao

  DOI：10.1021/jo00059a027

  日期：1993.3

  The allylic anion generated from 2-(N-methylanilino)-4-phenyl-3-butenenitrile (1) reacted with iodomethane and 3-bromo-1-chloropropane in THF/HMPA to give the gamma-substitution products exclusively, predominantly in the 2Z-configuration. Substitution of the N-methylanilino group with the methyl ether of L-(-)-ephedrine resulted in the generation of chiral aminonitrile 2. Lithiated 2 reacted sluggishly in THF with allyl bromide and benzyl chloride in the absence of HMPA to give the gamma-substitution products predominantly in the 2Z-configuration, with little diastereoselectivity. The aminonitrile 3 prepared from cinnamaldehyde, L-(-)-ephedrine, and KCN was lithiated with 2 equiv of LDA resulting in high facial selectivity (76-100% diastereomeric excess) in alkylations in the presence of HMPA and LiI. Lithiated 3 reacted with propionaldehyde, benzaldehyde, and p-bromobenzaldehyde at-78-degrees-C to give the gamma-addition products, predominantly in the 4R-configuration (64-78% de). The stereochemistry of the isomers of each product was determined by chemical correlation and spectral methods including analyses of the CD spectra and X-ray diffraction. A bicyclic transition state C wherein lithium is chelated by both amino and alkoxy groups is proposed to interpret the observed stereoselectivity.
• Touet, Joel; Baudouin, Sylvie; Brown, Eric, Journal of Chemical Research, Miniprint, 1996, # 5, p. 1251 - 1266
  作者：Touet, Joel、Baudouin, Sylvie、Brown, Eric

  DOI：——

  日期：——