1-carbethoxy-1-(trimethylsilyloxy)propene | 188530-93-0

• 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: 1-carbethoxy-1-(trimethylsilyloxy)propene
• 英文别名: Ethyl 2-[(trimethylsilyl)oxy]but-2-enoate；ethyl 2-trimethylsilyloxybut-2-enoate
• CAS: 188530-93-0
• 化学式: C₉H₁₈O₃Si
• 分子量: 202.326
• InChiKey: DGLHZNHGGFFQJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-carbethoxy-1-(trimethylsilyloxy)propene 在 Selectfluor 作用下， 以 乙腈 为溶剂， 生成 ethyl 3-fluoro-2-oxobutanoate
  参考文献：
  名称：

  Preparation of β-Fluoro-α-ketoesters from α-Ketoesters and Their Conversion to (Z)-β-Fluoro-α-aminoacrylate Derivatives

  摘要：

  DOI：

  10.1021/jo9806761
• 作为产物：
  描述：

  三甲基氯硅烷 、 2-丁酮酸乙酯 以 四氢呋喃 、 三乙胺 为溶剂， 生成 1-carbethoxy-1-(trimethylsilyloxy)propene
  参考文献：
  名称：

  Synthesis and Reactions of 3-(Nosyloxy)-2-keto Esters

  摘要：

  A series of 3-(nosyloxy)-2-keto esters 7a-j were prepared from the corresponding cr-keto esters by conversion to the trimethylsilyl enol ether and reaction with p-nitrobenzenesulfonyl peroxide. Conversion of these materials to 1,2,3-trifunctionalized compounds is described, and comparison of their properties with isomeric 2-(nosyloxy)-3-keto esters is discussed.

  DOI：

  10.1021/jo962206h

文献信息

• Synthesis of Rigid Receptors Based on Triphenylene Ketals
  作者：Matthias C. Schopohl、Andreas Faust、Daniela Mirk、Roland Fröhlich、Olga Kataeva、Siegfried R. Waldvogel

  DOI：10.1002/ejoc.200500108

  日期：2005.7

  The synthesis of rigid receptors based on triphenylene ketals, including some improved procedures, is described in detail. Since chemical transformations are strongly influenced by the rigid character and steric bulkiness of the receptors, the construction of a subunit allowing quicker synthetic development is also reported. The preparation of these receptor structures involves an oxidative trimerization

  详细描述了基于三亚苯基缩酮的刚性受体的合成，包括一些改进的程序。由于化学转化受受体的刚性特征和空间体积的强烈影响，因此还报道了允许更快合成发展的亚基的构建。这些受体结构的制备涉及氧化三聚和随后的重复异构化过程。讨论了空间要求亲和基团在受体支架和相应亚基上的连接范围，并通过一些晶体结构概述了手性修饰系统分子识别的分子结构和可用空间。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• A Novel Three-Component [3+2] Cycloannulation Process for the Rapid and Highly Stereoselective Synthesis of Pyrrolobenzoxazoles
  作者：Michael Boomhoff、Christoph Schneider

  DOI：10.1002/chem.201200405

  日期：2012.4.2

  Four new σ bonds and two chiral centers are formed in a novel three‐component, one‐pot [3+2] cycloannulation process, which gives pyrrolobenzoxazoles directly in good yields and with excellent diastereoselectivity (see scheme, TMS=trimethylsilyl). The products could be converted into proline derivatives with full stereochemical control. A chiral scandium complex catalyzed the formation of the products

  在一个新颖的三组分，一锅[3 + 2]环环化工艺中形成了四个新的σ键和两个手性中心，该环化工艺可直接获得吡咯并苯并恶唑，并具有良好的非对映选择性（参见方案，TMS =三甲基甲硅烷基）。可以在完全立体化学控制下将产物转化为脯氨酸衍生物。手性scan络合物以高达83％的ee催化产物的形成 。
• Synthesis and Reactions of 3-(Nosyloxy)-2-keto Esters
  作者：Robert V. Hoffman、M. Catherine Johnson、John F. Okonya

  DOI：10.1021/jo962206h

  日期：1997.4.1

  A series of 3-(nosyloxy)-2-keto esters 7a-j were prepared from the corresponding cr-keto esters by conversion to the trimethylsilyl enol ether and reaction with p-nitrobenzenesulfonyl peroxide. Conversion of these materials to 1,2,3-trifunctionalized compounds is described, and comparison of their properties with isomeric 2-(nosyloxy)-3-keto esters is discussed.
• Preparation of β-Fluoro-α-ketoesters from α-Ketoesters and Their Conversion to (<i>Z</i>)<i>-</i>β-Fluoro-α-aminoacrylate Derivatives
  作者：John F. Okonya、M. Catherine Johnson、Robert V. Hoffman

  DOI：10.1021/jo9806761

  日期：1998.9.1