methyl 3-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-(2-furyl)-2-methylenepropanoate | 169690-56-6

• 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: methyl 3-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-(2-furyl)-2-methylenepropanoate
• 英文别名: methyl 2-[(tert-butyldimethylsilyloxy)(furan-2-yl)methyl]acrylate；Methyl 2-[[tert-butyl(dimethyl)silyl]oxy-(furan-2-yl)methyl]prop-2-enoate
• CAS: 169690-56-6
• 化学式: C₁₅H₂₄O₄Si
• 分子量: 296.439
• InChiKey: LVNPHBKHYNSXLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-(2-furyl)-2-methylenepropanoate 在 氧气 、 rose bengal 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到methyl 2-[(tert-butyldimethylsilyloxy)(2-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)methyl]acrylate
  参考文献：
  名称：

  A tandem Baylis–Hillman-singlet oxygen oxidation reaction for facile synthesis of γ-substituted γ-hydroxybutenolides

  摘要：

  A series of highly functionalised gamma-hydroxyacryl gamma-hydroxybutenolides, 2, were synthesised in 25-50% overall yields in two or three steps from 2-furfural using a tandem Baylis-Hillman-singlet oxygen oxidation reaction. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.019
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 3-羟基-2-亚甲基-3-(2-呋喃基)丙酸甲酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以98%的产率得到methyl 3-(((1,1-dimethylethyl)dimethylsilyl)oxy)-3-(2-furyl)-2-methylenepropanoate
  参考文献：
  名称：

  A tandem Baylis–Hillman-singlet oxygen oxidation reaction for facile synthesis of γ-substituted γ-hydroxybutenolides

  摘要：

  A series of highly functionalised gamma-hydroxyacryl gamma-hydroxybutenolides, 2, were synthesised in 25-50% overall yields in two or three steps from 2-furfural using a tandem Baylis-Hillman-singlet oxygen oxidation reaction. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.019

文献信息

• Syn-Stereocontrolled dihydroxylation of Baylis-Hillman adducts
  作者：István E. Markó、Paul R. Giles、Zdenek Janousek、Nigel J. Hindley、Jean-Paul Declercq、Bernard Tinant、Janine Feneau-Dupont、John S. Svendsen

  DOI：10.1002/recl.19951140418

  日期：——

  The hydroxylation of Baylis-Hillman adducts 1 is shown to proceed with high levels of diastereocontrol. A mechanistic rationale to explain this selectivity is discussed.

  Baylis-Hillman加合物1的羟基化表现为高水平的非对映异构控制。讨论了解释这种选择性的机械原理。
• A Simple Route to .alpha.-Substituted-.beta.-Amino Ester Precursors of Carbapenem Antibiotics
  作者：Patrick Perlmutter、Mark Tabone

  DOI：10.1021/jo00125a043

  日期：1995.10

  A three-step process is presented for the preparation of alpha-substituted-beta-amino esters which can serve as precursors to a key intermediate in carbapenem synthesis. The pivotal reaction in this sequence involves a highly diastereoselective conjugate addition reaction. Two series of alkenoates bearing a stereogenic substituent attached to C2 were prepared and their conjugate addition reactions with benzylamine studied under several different sets of conditions. Conjugate addition of benzylamine to alkenoates 7a and 7d, in methanol at room temperature, gave adducts 8a and Sd with virtually complete anti-diastereoselectivity. These two beta-amino esters bear the correct relative stereochemistry and side chain to serve as precursors for carbapenem antibiotic synthetic intermediates. The role of the allylic substituents of the alkenoates 7a-e in determining the stereochemical outcome of these additions is discussed. These conjugate additions were explored further by the preparation and conjugate addition reactions of the alpha,beta-disubstituted alkenoates 15a and 15b. It was found that the presence of a beta-substituent led to a dramatic reduction in yield although the same anti-diastereoselectivity was maintained. The relative stereochemistry of the adducts was established by examination of the relevant coupling constants in the H-1 NMR spectra of their tetrahydro-1,3-oxazine derivatives.
• A tandem Baylis–Hillman-singlet oxygen oxidation reaction for facile synthesis of γ-substituted γ-hydroxybutenolides
  作者：Santoshkumar N. Patil、Benjamin E. Stephens、Fei Liu

  DOI：10.1016/j.tet.2008.09.019

  日期：2008.11

  A series of highly functionalised gamma-hydroxyacryl gamma-hydroxybutenolides, 2, were synthesised in 25-50% overall yields in two or three steps from 2-furfural using a tandem Baylis-Hillman-singlet oxygen oxidation reaction. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.