(2RS,3RS)-methyl 2-methyl-3-hydroxy-3-phenylbutyrate | 14366-99-5

• 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: (2RS,3RS)-methyl 2-methyl-3-hydroxy-3-phenylbutyrate
• 英文别名: methyl 3-hydroxy-2-methyl-3-phenylbutanoate；(2RS.3RS)-3-hydroxy-2-methyl-3-phenyl-butyric acid methyl ester；(2RS.3RS)-3-Hydroxy-2-methyl-3-phenyl-buttersaeure-methylester；erythro-3-Hydroxy-3-phenyl-2-methyl-buttersaeure-methylester；erythro-3-Phenyl-2-methyl-3-hydroxy-buttersaeuremethylester；methyl (2R,3R)-3-hydroxy-2-methyl-3-phenylbutanoate
• CAS: 14366-99-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: KOQCAMNBOCKXMR-JOYOIKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2RS,3RS)-methyl 2-methyl-3-hydroxy-3-phenylbutyrate 、 2,2'-二硫二吡啶 以71%的产率得到
  参考文献：
  名称：

  STEVENS, R. W.;IWASAWA, NOBUHARU;MUKAIYAMA, TERUAKI, CHEM. LETT., 1982, N 9, 1459-1462

  摘要：

  DOI：
• 作为产物：
  描述：

  (5S,6S)-5-Methyl-6-phenyl-4-pyrrolidin-1-yl-5,6-dihydro-pyran-2-one 在 高碘酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2RS,3RS)-methyl 2-methyl-3-hydroxy-3-phenylbutyrate
  参考文献：
  名称：

  A new protocol for the diastereoselective formation of lactones from either achiral or chiral vinylogous urethanes

  摘要：

  DOI：

  10.1021/jo00380a050

文献信息

• Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones
  作者：Han Yong Bae、Benjamin List

  DOI：10.1002/chem.201803142

  日期：2018.9.18

  The Mukaiyama aldol reaction is a widely applied carbon–carbon bond forming reaction. However, despite numerous well‐established methods using aldehydes as acceptors, only few examples exist with ketones. Here we report a highly practical catalytic approach to this transformation, namely, the triflimide catalyzed Mukaiyama aldol reaction of silyl ketene acetals with ketones. This method exhibits a

  Mukaiyama羟醛反应是一种广泛应用的碳-碳键形成反应。但是，尽管有许多使用醛作为受体的公认方法，但酮的例子很少。在这里，我们报告了一种非常实用的催化方法来进行这种转化，即三氟甲酰亚胺催化的甲硅烷基乙烯酮缩醛与酮的Mukaiyama aldol反应。该方法具有广泛的底物范围，非常快，可耐受功能化底物，并且仅需百万分之几的催化剂负载量即可进行制备级反应，纯度高达数百克（纯度> 99％）。
• Iron-Catalysed Reformatsky-Type Reactions
  作者：Muriel Durandetti、Jacques Périchon

  DOI：10.1055/s-2006-926432

  日期：2006.5

  A Reformatsky-type reaction has been developed using iron catalysis in acetonitrile or DMF. Reduction of iron(II) bromide by manganese metal in acetonitrile provides a low-valent iron catalyst, which is the active species; under these conditions, α-chloroesters or nitriles can both be converted into their corresponding derivatives. The method was applicable to both ketones and aldehydes, resulting in the formation of β-hydroxyesters under mild conditions.

  一种 Reformatsky 型反应已采用铁催化体系在乙腈或二甲基甲酰胺中得到开发。通过在乙腈中用锰金属还原二溴化铁，可得到低价铁催化剂，该催化剂为活性物种；在这些条件下，α-氯酯或腈均可转化为相应的衍生物。该方法适用于酮和醛，在温和条件下形成 β-羟基酯。
• Ni-catalyzed activation of α-chloroesters: a simple method for the synthesis of α-arylesters and β-hydroxyesters
  作者：Muriel Durandetti、Corinne Gosmini、Jacques Périchon

  DOI：10.1016/j.tet.2006.11.055

  日期：2007.1

  Coupling reactions of α-chloroesters with aryl halides (α-arylation) or carbonyl compounds (Reformatsky) using nickel catalyst allow, under mild conditions, the preparation of various functionalized aryl propionic acid derivatives or β-hydroxyesters. In the synthesis of aryl propionic acid derivatives, the process is efficient with aryl halides bearing either electron-withdrawing or electron-donating

  使用镍催化剂，α-氯酸酯与芳基卤化物（α-芳基化）或羰基化合物（Reformatsky）的偶联反应可以在温和的条件下制备各种官能化的芳基丙酸衍生物或β-羟基酯。在芳基丙酸衍生物的合成中，该方法对于带有带吸电子基团或给电子基团的芳基卤化物是有效的。
• Copper‐Catalyzed Enantioselective Reductive Aldol Reaction of α,β‐Unsaturated Carboxylic Acids to Alkyl Aryl Ketones: Silanes as Activator and Transient Protecting Group
  作者：Hirotsugu Suzuki、Kenji Yoneoka、Sora Kondo、Takanori Matsuda

  DOI：10.1002/chem.202104273

  日期：2022.2.16

  The first reductive aldol reaction of α,β-unsaturated carboxylic acids was developed in the presence of copper/bisphosphine catalysts. The reaction demonstrated the usability of in situ protection of α,β-unsaturated carboxylic acids by a hydrosilane for the reductive C−C bond formation. The Si−O bond in the aldol products is readily cleaved by a standard workup, showing the silane worked as not only

  α,β-不饱和羧酸的第一个还原醛醇反应是在铜/双膦催化剂存在下开发的。该反应证明了通过氢化硅烷原位保护α，β-不饱和羧酸以形成还原性C-C键的可用性。醛醇产物中的 Si-O 键很容易通过标准后处理裂解，这表明硅烷不仅可以用作活化剂，还可以用作临时保护基团。
• Copper Hydride-Catalyzed Conjugate Reduction-Aldol Addition Domino Reaction of<i>α</i>,<i>β</i>-Unsaturated Carboxylates with Ketones
  作者：Zengchang Li、Lan Jiang、Zhengning Li、Huiying Chen

  DOI：10.1002/cjoc.201300036

  日期：2013.4

  Copper hydride‐catalyzed conjugate reduction‐intermolecular aldol addition domino reactions were realized using α,β‐unsaturated carboxylates as hydride acceptors and a silane as the reducing reagent. High diastereoselectivities were achieved with 4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene as the ligand and tert‐butyl acrylate as the hydride acceptor.

  以α，β-不饱和羧酸盐为氢化物受体，以硅烷为还原剂，实现了氢化铜催化的共轭还原-分子间羟醛加成多米诺反应。以4,5-双（二苯基膦基）-9,9-二甲基x吨为配体，以丙烯酸叔丁酯为氢化物受体实现了较高的非对映选择性。