1-(N-methyl-2-pyrrolyl)-1-(trimethylsilyloxy)ethylene | 119612-86-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(N-methyl-2-pyrrolyl)-1-(trimethylsilyloxy)ethylene
• 英文别名: 1-methyl-2-(1-((trimethylsilyl)oxy)vinyl)-1H-pyrrole；trimethyl-[1-(1-methylpyrrol-2-yl)ethenoxy]silane
• CAS: 119612-86-1
• 化学式: C₁₀H₁₇NOSi
• 分子量: 195.337
• InChiKey: KIVSERMICHZWRE-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 2 Torr)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 1-(N-methyl-2-pyrrolyl)-1-(trimethylsilyloxy)ethylene 以 甲苯 为溶剂， 反应 22.0h， 以34%的产率得到5-(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-6-methyl-2-phenyl-5-trimethylsilanyloxy-4,5,6,8b-tetrahydro-3aH-pyrrolo[3,4-e]indole-1,3-dione
  参考文献：
  名称：

  N-取代的2-乙酰基吡咯的甲硅烷基烯醇醚与吲哚骨架的[4 + 2]环加成反应中的不同过程

  摘要：

  取决于N-取代基，标题反应的发生是通过多种不同的重新芳构化过程进行的：空气氧化（N-乙氧羰基），PhSO 2和Me 3 Si基团（N-苯磺酰基）的消除或烯与另一双亲二烯体（N-甲基）的反应。

  DOI：

  10.1016/s0040-4039(00)97689-5
• 作为产物：
  描述：

  2-乙酰基-1-甲基吡咯 生成 1-(N-methyl-2-pyrrolyl)-1-(trimethylsilyloxy)ethylene
  参考文献：
  名称：

  Saalfrank, Rolf W.; Guendel, Juergen; Rossmann, Guenther, Chemische Berichte, 1990, vol. 123, # 5, p. 1175 - 1183

  摘要：

  DOI：

文献信息

• Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2<i>H</i>-cyclohepta[<i>b</i>]furan-2-ones with silyl enol ethers
  作者：Taku Shoji、Shuhei Sugiyama、Yoshiaki Kobayashi、Akari Yamazaki、Yukino Ariga、Ryuzi Katoh、Hiroki Wakui、Masafumi Yasunami、Shunji Ito

  DOI：10.1039/c9cc09376a

  日期：——

  We developed a procedure for the direct synthesis of 2-arylazulenes, which were obtained in moderate to excellent yields, by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with aryl-substituted silyl enol ethers. The structures of some 2-arylazulenes were clarified by single-crystal X-ray analysis. The 2-phenylazulene derivatives obtained by this study showed noticeable fluorescence in acidic

  我们开发了一种直接合成2-芳基azulenes的程序，该方法可以通过2H-环庚[b]呋喃-2-酮与芳基取代的甲硅烷基烯醇醚的[8 + 2]环加成反应而以中等至极好的收率获得。通过单晶X射线分析澄清了一些2-芳基az嗪的结构。通过该研究获得的2-苯基氮杂烯衍生物在酸性介质中显示出明显的荧光。
• Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers
  作者：Vyacheslav I Supranovich、Vitalij V Levin、Alexander D Dilman

  DOI：10.3762/bjoc.16.126

  日期：——

  light-mediated fluoroalkylation of silyl enol ethers with (bromodifluoromethyl)trimethylsilane followed by a reduction of the primary products with sodium borohydride is described. An 18 W, 375 nm LED was used as the light source. The reaction is performed in the presence of a gold photocatalyst, which effects the generation of a (trimethylsilyl)difluoromethyl radical via cleavage of the carbon–bromine

  描述了一种用（溴二氟甲基）三甲基硅烷将甲硅烷基烯醇醚进行光介导的氟代烷基化，然后用硼氢化钠还原初级产物的方法。使用18 W，375 nm的LED作为光源。该反应在金光催化剂的存在下进行，金光催化剂通过碳-溴键的裂解影响（三甲基甲硅烷基）二氟甲基自由基的产生。
• Simplification of antitumoral phenanthroindolizidine alkaloids: Short synthesis of cytotoxic indolizidinone and pyrrolidine analogs
  作者：Javier Miguélez、Alicia Boto、Raquel Marín、Mario Díaz

  DOI：10.1016/j.ejmech.2013.06.009

  日期：2013.8

  Hydroxylated seco-analogs of cytotoxic phenanthroindolizidine alkaloids were prepared in good yields from inexpensive 4-hydroxyproline derivatives, in just two steps. Thus, a sequential oxidative radical scission–oxidation was used for the direct conversion of the proline derivative into a 2-(2-aryl-oxoethyl)pyrrolidine with a variety of aryl and heteroaryl groups. The 4R-stereogenic center allowed

  只需两步，即可从廉价的4-羟基脯氨酸衍生物中以高收率制备细胞毒性的菲咯啉吲哚嗪生物碱的羟基化类似物。因此，顺序氧化自由基的断裂-氧化被用于脯氨酸衍生物直接转化为带有各种芳基和杂芳基的2-（2-芳基-氧乙基）吡咯烷。4 R-立体异构中心可方便地进行异构体分离，并在引入新链时进行立体控制（有趣的是，2,4-顺式异构体为主）。在第二步中，环化反应提供了带有吲哚并吲哚酮核心的生物碱类似物；发生部分异构化，但异构体易于纯化。然后比较了双环吲哚并二酮和更简单的吡咯烷衍生物对致瘤性人神经元SHSY-5Y和乳腺癌MCF7细胞的细胞毒活性。所有联苯衍生物均表现出有效的活性（一种化合物在微摩尔剂量下在两种肿瘤细胞中均导致> 80％的细胞死亡），在吡咯烷酮和吲哚齐酮酮系列中可比。
• Nickel catalyzed dealkoxylative C_sp2–C_sp3 cross coupling reactions – stereospecific synthesis of allylsilanes from enol ethers
  作者：Lin Guo、Matthias Leiendecker、Chien-Chi Hsiao、Christoph Baumann、Magnus Rueping

  DOI：10.1039/c4cc08187k

  日期：——

  The application of cyclic and acyclic enol ethers as electrophiles in cross coupling reactions offers new possibilities for the preparation of functional compounds.

  环状和非环状烯醇醚作为亲电试剂在交叉偶联反应中的应用为功能化合物的制备提供了新的可能性。
• Synthesis of indolizidinone analogues of cytotoxic alkaloids: Monocyclic precursors are also active
  作者：Alicia Boto、Javier Miguélez、Raquel Marín、Mario Díaz

  DOI：10.1016/j.bmcl.2012.03.109

  日期：2012.5

  Readily available proline derivatives can be transformed in just two steps into analogues of cytotoxic phenanthroindolizidine alkaloids. The key step uses a sequential radical scission-oxidation-alkylation process, which yields 2-substituted pyrrolidine amides. A second process effects the cyclization to give the desired alkaloid analogues, which possess an indolizidine core. The major and minor isomers (dr 3:2 to 3:1) can be easily separated, allowing their use to study structure-activity relationships (SAR). The process is versatile and allows the introduction of aryl and heteroaryl groups (including biphenyl, halogenated phenyl, and pyrrole rings). Some of these alkaloid analogues displayed a selective cytotoxic activity against tumorogenic human neuronal and mammary cancer cells, and one derivative caused around 80% cell death in both tumor lines at micromolar doses. The cytotoxicity of some monocyclic precursors was also studied, being comparable or superior to the bicyclic derivatives. (C) 2012 Elsevier Ltd. All rights reserved.