3-hydroxy-2-methyl-3-phenyl-propionic acid | 23985-58-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-hydroxy-2-methyl-3-phenyl-propionic acid
• 英文别名: 2-methyl-3-phenyl-3-hydroxypropionic acid；3-Hydroxy-2-methyl-3-phenyl-propionsaeure；β-Hydroxy-α-methyl-β-phenyl-propionsaeure；β-Oxy-α-methyl-hydrozimtsaeure；α-Oxy-α-phenyl-propan-β-carbonsaeure；β-Oxy-β-phenyl-isobuttersaeure；3-hydroxy-2-methyl-3-phenylpropanoic acid
• CAS: 23985-58-2
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: JWISPMMVFLKFMW-UHFFFAOYSA-N

物化性质

• 熔点：
  77 °C
• 沸点：
  331.7±30.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-methyl-3-phenyl-propionic acid 在 乙酸酐 作用下， 生成 2-甲基-3-苯基丙烯酸
  参考文献：
  名称：

  Dain, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1897, vol. 29, p. 607,609

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-3-氧代-3-苯基丙酸乙酯 在 甲醇 、 钯 作用下， 生成 3-hydroxy-2-methyl-3-phenyl-propionic acid
  参考文献：
  名称：

  Bodendorf; Krueger; Zernial, Justus Liebigs Annalen der Chemie, 1949, vol. 562, p. 1,10

  摘要：

  DOI：

文献信息

• Catalyst composition for hydrogenation and method for hydrogenation using the same
  申请人：Asahi Kasei Chemicals Corporation

  公开号：US10016749B2

  公开（公告）日：2018-07-10

  A catalyst composition for hydrogenation including (A) to (D), in which a mass ratio ((C)/(A)) is 0.1 to 4.0 and a mass ratio ((D)/(A)) is 0.01 to 1.00, (A): a titanocene compound represented by formula (1), (wherein R5 and R6 are any group selected from hydrogen, a hydrocarbon group having 1 to 12 carbon atoms, an aryloxy group, an alkoxy group, a halogen group, and a carbonyl group. R1 and R2 are any group selected from the group consisting of hydrogen and a hydrocarbon group having 1 to 12 carbon atoms, and R1 and R2 are not all hydrogen atoms or all a hydrocarbon group having 1 to 12 carbon atoms), (B): a reductant formed from a compound containing an element selected from the elements Li, Na, K, Mg, Zn, Al, and Ca, (C): an unsaturated compound having a molecular weight of 400 or less, and (D): a polar compound.

  一种用于加氢的催化剂组合物，包括(A)至(D)，其中质量比((C)/(A))为0.1至4.0，质量比((D)/(A))为0.01至1.00， (A)：由公式(1)表示的钛环戊二烯基化合物， （其中R5和R6是从氢、具有1至12个碳原子的烃基、芳氧基、烷氧基、卤素基和羰基中选择的任何基团。R1和R2是从氢和具有1至12个碳原子的烃基组成的组中选择的任何基团，且R1和R2不全是氢原子或全部为具有1至12个碳原子的烃基）， (B)：由含有选自Li、Na、K、Mg、Zn、Al和Ca元素的化合物的还原剂形成， (C)：分子量400或以下的非饱和化合物，以及 (D)：极性化合物。
• Ligand-Promoted, Boron-Mediated Chemoselective Carboxylic Acid Aldol Reaction
  作者：Hideoki Nagai、Yuya Morita、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/acs.orglett.6b00914

  日期：2016.5.6

  selective aldol reaction mediated by boron compounds and a mild organic base (DBU) was developed. Inclusion of electron-withdrawing groups in the amino acid derivative ligands reacted with BH3·SMe2 forms a boron promoter with increased Lewis acidity at the boron atom and facilitated the carboxylic acid selective enolate formation, even in the presence of other carbonyl groups such as amides, esters, ketones

  开发了由硼化合物和温和的有机碱（DBU）介导的第一个羧酸选择性羟醛反应。与BH 3 ·SMe 2反应的氨基酸衍生物配体中包含吸电子基团，形成硼促进剂，在硼原子上路易斯酸度增加，即使在存在其他羰基如酰胺，酯，酮或脂族醛。出色的配体效应导致了包括生物相关化合物在内的广泛底物范围。
• Siloxy Esters as Traceless Activators of Carboxylic Acids: Boron‐Catalyzed Chemoselective Asymmetric Aldol Reaction**
  作者：Taiki Fujita、Mina Yamane、W. M. C. Sameera、Harunobu Mitsunuma、Motomu Kanai

  DOI：10.1002/anie.202109788

  日期：2021.11.8

  We developed a chiral boron-catalyzed, carboxylic acid-selective asymmetric aldol reaction applicable to multifunctional substrates at late stages for the first time. Computational studies rationalized the reaction mechanism and stereoselectivity through Si/B enediolates acting as the active species.

  我们首次开发了一种手性硼催化的、羧酸选择性不对称羟醛反应，该反应适用于后期阶段的多功能底物。计算研究通过作为活性物质的 Si/B 烯二醇使反应机制和立体选择性合理化。
• Asymmetric Diels−Alder, Michael, and Aldol Reactions Using a Planar Chiral 1,3-Oxazol-2(3<i>H</i>)-one Derived from (<i>R</i>)-(+)-4-Hydroxy-[2.2]paracyclophane
  作者：Antonio Cipiciani、Francesco Fringuelli、Oriana Piermatti、Ferdinando Pizzo、Renzo Ruzziconi

  DOI：10.1021/jo016383g

  日期：2002.4.1

  (+)-(R)-[2.2]Paracyclophane[4,5-d]-1,3-oxazol-2(3H)-one exhibiting planar chirality has been used as a chiral auxiliary in asymmetric Diels-Alder, Michael, and aldol reactions of alpha,beta-unsaturated carboxy and enolate imides, respectively. The endo-exo- and face-diastereoselectivity is good and is controlled by the spatial relationship between the prochiral center and the C9-C10 ethylene bridge

  （+）-（R）-[2.2]吡喃环[4,5-d] -1,3-恶唑-2（3H）-具有平面手性的化合物已被用作不对称Diels-Alder的手性助剂，Michael，和α，β-不饱和羧基和烯醇酰亚胺的醛醇缩合反应。内-外-对-非-对映体选择性良好，并由前手性中心与[2.2]对环环烷部分的C9-C10亚乙基桥之间的空间关系控制。手性助剂易于除去并定量回收。
• Aldol reactions on solid phase. Sc(OTf)3-Catalyzed aldol reactions of polymer-supported silyl enol ethers with aldehydes providing convenient methods for the preparation of 1,3-diol, β-hydroxy carboxylic acid, and β-hydroxy aldehyde libraries
  作者：Shü Kobayashi、Iwao Hachiya、Masaru Yasuda

  DOI：10.1016/0040-4039(96)01158-6

  日期：1996.7

  Aldol reactions on solid phase have been achieved. In the presence of a catalytic amount of scandium triflate (Sc(OTf)3), polymer-supported silyl enol ethers reacted with aldehydes to afford the corresponding β-hydroxy thioester derivatives, which were reduced to 1,3-diol and β-hydroxy aldehyde derivatives, or hydrolyzed to β-hydroxy carboxylic acid derivatives.

  已经实现了固相上的醛醇缩合反应。在催化量的三氟甲磺酸scan（Sc（OTf）3）存在下，聚合物负载的甲硅烷基烯醇醚与醛反应，得到相应的β-羟基硫代酯衍生物，将其还原为1,3-二醇和β-羟基醛衍生物，或水解为β-羟基羧酸衍生物。