2-methoxycarbonyl-1-phenyl-1-trimethylsilyloxypropene | 281195-04-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-methoxycarbonyl-1-phenyl-1-trimethylsilyloxypropene
• 英文别名: Methyl 2-[phenyl(trimethylsilyloxy)methyl]prop-2-enoate；methyl 2-[phenyl(trimethylsilyloxy)methyl]prop-2-enoate
• CAS: 281195-04-8
• 化学式: C₁₄H₂₀O₃Si
• 分子量: 264.397
• InChiKey: OBPDRQGLFFWHNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-methoxycarbonyl-1-phenyl-1-trimethylsilyloxypropene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 3.0h， 生成 (2S,3R)-methyl 3-hydroxy-2-methyl-3-phenylpropionate 、 methyl 3-hydroxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  Diastereoselective heterogeneous catalytic hydrogenation of Baylis–Hillman adducts

  摘要：

  We describe herein our results concerning a highly diastereoselective heterogeneous hydrogenation of Baylis-Hillman adducts obtained from aromatic aldehydes. The results obtained are complementary to those already described for homogeneous catalytic hydrogenation reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00258-6
• 作为产物：
  描述：

  2-(羟基苯基甲基)-丙烯酸甲酯 、 六甲基二硅氮烷 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以98%的产率得到2-methoxycarbonyl-1-phenyl-1-trimethylsilyloxypropene
  参考文献：
  名称：

  A FACILE CONVERSION OF THE BAYLIS-HILLMAN ADDUCTS INTO TRIMETHYLSILYL ETHERS WITH HEXAMETHYLDISILAZANE CATALYSED BY IODINE

  摘要：

  The hydroxy group of the Baylis-Hillman adducts was protected with trimethylsilyl (TMS) group using the reaction of adducts la-h with hexamethyldisilazane (HMDS) catalyzed by iodine under nearly neutral reaction conditions.

  DOI：

  10.1080/10426500490459803

文献信息

• Silicon-based Bulky Group−Tuned Parallel Kinetic Resolution in Copper-Catalyzed 1,3-Dipolar Additions
  作者：Yang Yuan、Zhan-Jiang Zheng、Li Li、Xing-Feng Bai、Zheng Xu、Yu-Ming Cui、Jian Cao、Ke-Fang Yang、Li-Wen Xu

  DOI：10.1002/adsc.201800220

  日期：2018.8.17

  structurally different types of amino acid derivatives via chemodivergent [3+2] cycloaddition reactions and tandem conjugate addition‐elimination reaction respectively. The resulting and structurally divergent enantioenriched amino acid derivatives that contain four contiguous stereogenic centers and an all‐carbon quaternary center were obtained with up to 99% ee with >95:1 dr and good yields.

  研发新的策略或反应过程以激发官能团的新反应性，这继续促使合成化学家们寻求使用新化合物的创新解决方案。在本文中，我们发现硅基庞大的基团使1,3-偶极加成引发的平行动力学拆分（PKR）意外发生，从而导致通过化学发散[3]产生两种结构不同类型的氨基酸衍生物的高度对映选择性[3]。 +2]分别为环加成反应和串联共轭加消除反应。得到的结果和结构上不同的对映体富集的氨基酸衍生物包含四个连续的立体生成中心和一个全碳四元中心，其ee高达99％，dr大于95：1 和高产量。
• A FACILE CONVERSION OF THE BAYLIS-HILLMAN ADDUCTS INTO TRIMETHYLSILYL ETHERS WITH HEXAMETHYLDISILAZANE CATALYSED BY IODINE
  作者：Manouchehr Mamaghani、Abed Badrian

  DOI：10.1080/10426500490459803

  日期：2004.6

  The hydroxy group of the Baylis-Hillman adducts was protected with trimethylsilyl (TMS) group using the reaction of adducts la-h with hexamethyldisilazane (HMDS) catalyzed by iodine under nearly neutral reaction conditions.
• Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)
  作者：Marjan Jereb

  DOI：10.1016/j.tet.2012.03.040

  日期：2012.5

  An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol%) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process. (C) 2012 Elsevier Ltd. All rights reserved.
• Diastereoselective heterogeneous catalytic hydrogenation of Baylis–Hillman adducts
  作者：Cristiano R Mateus、Wanda P Almeida、Fernando Coelho

  DOI：10.1016/s0040-4039(00)00258-6

  日期：2000.4

  We describe herein our results concerning a highly diastereoselective heterogeneous hydrogenation of Baylis-Hillman adducts obtained from aromatic aldehydes. The results obtained are complementary to those already described for homogeneous catalytic hydrogenation reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.