(S)-methyl 3-(4-methoxyphenyl)-3-phenylpropanoate | 1413936-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-methyl 3-(4-methoxyphenyl)-3-phenylpropanoate
• 英文别名: methyl (3S)-3-(4-methoxyphenyl)-3-phenylpropanoate
• CAS: 1413936-31-8
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: XYJSFMQRJILYSI-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙炔酸甲酯 在 甲基二乙氧基硅烷 、 C₂₂H₃₁N₂O₇Rh 、 copper (I) acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 (S)-methyl 3-(4-methoxyphenyl)-3-phenylpropanoate
  参考文献：
  名称：

  Enantioselective Synthesis of Optically Active 3,3-Diarylpropanoates by Conjugate Hydrosilylation with Chiral Rh-bis(oxazolinyl)phenyl Catalysts

  摘要：

  Conjugate hydrosilylation of 3,3-diarylacrylate derivatives catalyzed by chiral rhodium-bis(oxazolinyl)phenyl complexes (1 mol %) at 60 degrees C for 2 h was investigated to prepare optically active 3,3-diarylpropanoate derivatives in high yields up to 99% yield and high enantioselectivities up to 99%.

  DOI：

  10.1021/jo302357b

文献信息

• Development of Modifiable Bidentate Amino Oxazoline Directing Group for Pd-Catalyzed Arylation of Secondary CH Bonds
  作者：Kang Chen、Zhao-Wei Li、Peng-Xiang Shen、Hong-Wei Zhao、Zhang-Jie Shi

  DOI：10.1002/chem.201406528

  日期：2015.5.11

  A novel bidentate α‐amino oxazolinyl directing group has been developed. Different from previous directing groups, this newly designed directing group was easily prepared from amino acids and modified in structure. This auxiliary preferentially effects functionalization at secondary C(sp3)H bonds, rather than at aryl C(sp2)H bonds. The diastereoselectivity of direct arylation between geminal secondary

  一个新的双齿α-氨基恶唑啉基导向基团已经开发出来。与以前的指导小组不同，这个新设计的指导小组很容易从氨基酸制备并进行结构修饰。该辅助剂优先在二级C（sp 3）H键上而不是在芳基C（sp 2）H键上进行功能化。线性分子中的双键仲C（sp 3）H键之间直接芳基化的非对映选择性也首次通过远程手性中继与手性导向基团实现。通过改变底物和芳基卤化物的取代基，可以用相同的手性来源制得两种非对映异构体。
• Iridium-Catalyzed Asymmetric Hydrogenation Yielding Chiral Diarylmethines with Weakly Coordinating or Noncoordinating Substituents
  作者：Päivi Tolstoy、Mattias Engman、Alexander Paptchikhine、Jonas Bergquist、Tamara L. Church、Abby W.-M. Leung、Pher G. Andersson

  DOI：10.1021/ja9013375

  日期：2009.7.1

  in pharmaceuticals and natural products, making the synthetic methods that form these chiral centers are important in industry. We have applied iridium complexes with novel N,P-chelating ligands to the asymmetric hydrogenation of trisubstituted olefins, forming diarylmethine chiral centers in high conversions and excellent enantioselectivities (up to 99% ee) for a broad range of substrates. Our results

  含二芳基次甲基的立体中心存在于药物和天然产物中，使得形成这些手性中心的合成方法在工业中很重要。我们已将具有新型 N,P 螯合配体的铱配合物应用于三取代烯烃的不对称氢化，以高转化率和优异的对映选择性（高达 99% ee）形成二芳基次甲基手性中心，适用于广泛的底物。我们的结果支持这样一种假设，即催化剂一个特定区域的空间位阻在立体选择中起着关键作用，因为在前手性碳上几乎没有差异的底物的氢化以高对映选择性发生。结果，即使当前手性碳带有例如苯基和对甲苯基基团时，也能获得出色的立体辨别力。
• Asymmetric NaBH₄1,4-Reduction of C3-Disubstituted 2-Propenoates Catalyzed by a Diamidine Cobalt Complex
  作者：Yoshihiro Shuto、Tomoya Yamamura、Shinji Tanaka、Masahiro Yoshimura、Masato Kitamura

  DOI：10.1002/cctc.201500260

  日期：2015.5.18

  unique diamidine ligand catalyzes asymmetric NaBH4 reduction of C3‐disubstituted (E)‐ and (Z)‐2‐propenoates, including C3‐oxygen‐ and nitrogen‐substituted substrates with high enantioselectivity. Analysis by X‐ray diffraction, 1H NMR spectroscopy, ring‐opening radical‐clock and D‐labeling reactions, and the structure/selectivity relationship suggest that a mechanism of CoH‐involved non‐single‐electron transfer

  独特的二am基配体的新Co络合物催化NaBH 4还原不对称还原C3-二取代的（E）和（Z）-2-丙烯酸酯，包括具有高对映选择性的C3-氧和氮取代的底物。X射线衍射，1 H NMR光谱，开环自由基钟和D标记反应以及结构/选择性关系的分析表明，CoH参与的非单电子转移1,4加成的机理有所不同C2对映体。新型CoH 2（BH 3）2配合物的定量分离已支持了CoH物种的参与。
• Palladium-Catalyzed Asymmetric Arylation of C(sp³)–H Bonds of Aliphatic Amides: Controlling Enantioselectivity Using Chiral Phosphoric Amides/Acids
  作者：Shao-Bai Yan、Song Zhang、Wei-Liang Duan

  DOI：10.1021/acs.orglett.5b00968

  日期：2015.5.15

  Enantioselective arylation of secondary beta-C(sp(3))-H bonds of 8-aminoquinoline amides was realized with a palladium catalyst. Chiral phosphoric amides and acids were used for the first time to control the stereoselectivity at the C-H bond cleavage step in the C-H activation reactions.