Methyl 2-Methyl-3-phenyl-3-(trimethylsiloxy)propionate | 57956-45-3

• 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: Methyl 2-Methyl-3-phenyl-3-(trimethylsiloxy)propionate
• 英文别名: methyl 2-methyl-3-phenyl-3-trimethylsilyloxypropanoate
• CAS: 57956-45-3
• 化学式: C₁₄H₂₂O₃Si
• 分子量: 266.412
• InChiKey: XEEBCMYOIQGNAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-Methyl-3-phenyl-3-(trimethylsiloxy)propionate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3-hydroxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  DMSO中简单的环氧三甲基硅烷的自发羟醛和迈克尔加成

  摘要：

  已证明偶极非质子传递溶剂可活化简单的三甲基甲硅烷基乙烯酮缩醛，可在极其简单，温和且无金属的条件下有效地添加助溶剂的羟醛和迈克尔。

  DOI：

  10.1016/s0040-4039(00)00725-5
• 作为产物：
  描述：

  [1-methoxyprop-1-enyloxy]trimethylsilane 、 苯甲醛 在 {1,2-benzenediolato^(2-)-O,O'}oxotitanium 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到Methyl 2-Methyl-3-phenyl-3-(trimethylsiloxy)propionate
  参考文献：
  名称：

  [1,2-Benzenediolato(2−)-O-O′]oxotitanium. A Chemoselective and Efficient Catalyst for Aldol-type Reaction of Ketene Silyl Acetals with Aldehydes

  摘要：

  在少量[1,2-苯二醇酸(2−)-O,O']氧合钛的催化下，酮烯硅缩醛能在温和条件下顺利与醛反应，以良好产率得到相应的β-羟基羧酸酯。根据这一方法，醛基被选择性激活，而酸敏性的缩醛基团保持不变。

  DOI：

  10.1246/cl.1989.1909

文献信息

• Mesoporous aluminosilicate-catalyzed Mukaiyama aldol reaction of aldehydes and acetals
  作者：Suguru Ito、Kenji Tanuma、Kohei Matsuda、Akira Hayashi、Hirotomo Komai、Yoshihiro Kubota、Masatoshi Asami

  DOI：10.1016/j.tet.2014.09.073

  日期：2014.11

  A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both aldehydes and acetals with silyl enol ethers or ketene silyl acetals to give the corresponding aldol adducts in moderate to high yields. The remarkable high catalytic activity of Al-MCM-41 over amorphous silica-alumina and aluminum-free mesoporous silicate was observed in the reaction

  发现介孔铝硅酸盐（Al-MCM-41）是醛和缩醛与甲硅烷基烯醇醚或乙烯酮甲硅烷基缩醛反应以产生中等至高收率的相应羟醛加合物的有效多相催化剂。在反应中观察到Al-MCM-41对无定形二氧化硅-氧化铝和无铝介孔硅酸盐具有显着的高催化活性。固体酸催化剂可通过过滤容易地回收，并且回收的催化剂可在相同反应中重复使用，而不会显着降低催化活性。
• [1,2-Benzenediolato(2−)-<i>O</i>-<i>O</i>′]oxotitanium. A Chemoselective and Efficient Catalyst for Aldol-type Reaction of Ketene Silyl Acetals with Aldehydes
  作者：Ryuichiro Hara、Teruaki Mukaiyama

  DOI：10.1246/cl.1989.1909

  日期：1989.11

  In the presence of a catalytic amount of [1,2-benzenediolato(2−)-O,O′]oxotitanium, ketene silyl acetals smoothly react with aldehydes to afford the corresponding β-hydroxy carboxylic esters in good yields under mild conditions. According to this procedure, an aldehyde group is selectively activated, while an acid labile acetal group remains intact.

  在少量[1,2-苯二醇酸(2−)-O,O']氧合钛的催化下，酮烯硅缩醛能在温和条件下顺利与醛反应，以良好产率得到相应的β-羟基羧酸酯。根据这一方法，醛基被选择性激活，而酸敏性的缩醛基团保持不变。
• Monofluoration stereoselective par le phenyltetrafluorophosphorane (PhPF4) Part. II. Application a la synthese des isomeres thréo et érythro des alkyl-2 fluoro-3 phenylpropanoates de methyle. Analyse conformationnelle par R.M.N. de 19F et 1H.
  作者：A.I. Ayi、M. Remli、R. Guedj、R. Pastor

  DOI：10.1016/s0022-1139(00)85258-6

  日期：1981.2
• Mukaiyama Aldol Reactions Catalyzed by Zirconocene Bis(triflate) Complexes:  Stereochemistry and Mechanisms for C−C Bond Formation
  作者：Shuqiong Lin、Georgiy V. Bondar、Christopher J. Levy、Scott Collins

  DOI：10.1021/jo971803g

  日期：1998.3.1

  The aldol condensations of alpha- and beta-(benzyloxy) aldehydes with enol silanes, catalyzed by Cp2Zr(OTf)(2) . THF or Cp2Zr(OTf)(2), in a variety of solvents were studied. The simple diastereoselectivity of these reactions is modest and comparable to that observed using simple aldehydes of similar steric requirements. Studies have revealed that TMSOTf is directly produced on reaction with the zirconocene catalyst with the enol silane in nitroalkane solvent or is formed during catalysis in dichloromethane solution. Although TMSOTf is known to catalyze cross-aldol reactions under these conditions, the rate of this process is not always competitive with that observed using the zircanocene catalysts. In particular, sterically unhindered or aromatic aldehydes react via a mechanism that appears to be mainly Zr-catalyzed, based on both the difference in rate between Zr- and Si-mediated reactions as well as differences in enol silane/silyl triflate reactivity in crossover-type experiments. With sterically hindered aldehydes in dichloromethane or nitromethane, catalysis is mediated by Si. The Zr-catalyzed process occurs via formation of a Zr-aldolate complex from aldehyde and enol silane, with liberation of TMSOTf, followed by rate-limiting O-silylatian of the metal aldolate by TMSOTf, as revealed by both model studies and in situ monitoring during catalysis.
• AYI A. I.; REMLI M.; GUEDJ R., J. FLUOR. CHEM., 1980, 16, NO 6, 559
  作者：AYI A. I.、 REMLI M.、 GUEDJ R.

  DOI：——

  日期：——