2-(triethylsilyl)furan | 1578-32-1

• 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: 2-(triethylsilyl)furan
• 英文别名: 2-triethylsilylfuran；triethyl-furan-2-yl-silane；Triethyl-(2-furyl)-silan；2-Furyl-triethylsilan；2-Triethyl-silylfuran；triethyl(furan-2-yl)silane
• CAS: 1578-32-1
• 化学式: C₁₀H₁₈OSi
• 分子量: 182.338
• InChiKey: CQVYWIWUMGAFKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(triethylsilyl)furan 在 正丁基锂 、 dihydrogen hexachloroplatinate(IV) hexahydrate 作用下， 以 乙醚 、 正己烷 、 异丙醇 为溶剂， 反应 16.17h， 生成 Triethyl-[5-[1-(3-piperidin-1-ylpropyl)silinan-1-yl]furan-2-yl]silane
  参考文献：
  名称：

  1- {3- [1-（5-（5-有机基甲硅烷基呋喃-2-基）硅兰-1-基]丙基}胺的合成及细胞毒活性及一些三甲基锗基类似物

  摘要：

  新的高度细胞毒性1- {3- [1-（5- organylsilyl -呋喃-2-基）silinan -1-基]丙基}胺和一些trimethylgermyl类似物（IC 50 1-7微克毫升-1）已经通过合成在Speier催化剂的存在下，脂肪族和杂环N-烯丙胺的氢化硅烷化反应。研究了硅环，呋喃环第5位的元素有机取代基以及胺的结构对新化合物的细胞毒性的影响。

  DOI：

  10.1002/chem.201402865
• 作为产物：
  描述：

  呋喃 、 三乙基硅烷 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 1,2-二[(2R,5R)-2,5-二异丙基磷杂环戊烷基]乙烷 、 环己烯 作用下， 以 neat (no solvent) 为溶剂， 反应 20.0h， 以91%的产率得到2-(triethylsilyl)furan
  参考文献：
  名称：

  Intermolecular C–H Silylation of Arenes and Heteroarenes with HSiEt₃under Operationally Diverse Conditions: Neat/Stoichiometric and Acceptor/Acceptorless

  摘要：

  Efficient protocols for Rh-catalyzed intermolecular C-H silylation of unactivated arenes and heteroarenes are disclosed. The silylations are catalyzed by a Rh-complex (2 mol %) derived in situ from commercially available Rh(nbd)(2)BF4 and (S,S)-i-Pr-BPE (L3) with Et3SiH in the presence of hydrogen acceptor under either neat (excess of arene) or stoichiometric conditions. The regioselectivity is determined mainly by the steric bulk of the substituents and by the electronic effect as an ancillary factor. In addition, our preliminary result shows that the current protocol catalyzes the silylation of arenes in the absence of hydrogen acceptors.

  DOI：

  10.1021/acscatal.5b02806

文献信息

• Synthesis and cytotoxic activity of new 2-[(3-aminopropyl)dimethylsilyl]-5-triethylsilylfurans
  作者：Luba Ignatovich、Velta Muravenko、Irina Shestakova、Ilona Domrachova、Juris Popelis、Edmunds Lukevics

  DOI：10.1002/aoc.1538

  日期：2010.3

  Highly cytotoxic 3‐aminopropyl derivatives of 5‐triethylsilyl‐2‐dimethylsilylfuran (LC501–3 µg ml−1) have been prepared by hydrosilylation of heterocyclic N‐allylamines with corresponding hydrosilane in the presence of Speier's catalyst. The influence of the amine structure on the cytotoxicity has been investigated. Copyright © 2009 John Wiley & Sons, Ltd.

  在Speier催化剂的存在下，通过杂环N-烯丙胺与相应的氢硅烷的氢化硅烷化反应，制得了5-三乙基甲硅烷基-2-二甲基甲硅烷基呋喃具有高度细胞毒性的3-氨基丙基衍生物（LC 50 1–3 µg ml -1）。已经研究了胺结构对细胞毒性的影响。版权所有©2009 John Wiley＆Sons，Ltd.
• Biarylmethane and Fused Heterocyclic Arene Synthesis via in Situ Generated <i>o</i>- and/or <i>p</i>-Naphthoquinone Methides
  作者：Yoshinari Sawama、Takahiro Kawajiri、Shota Asai、Naoki Yasukawa、Yuko Shishido、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1021/acs.joc.5b00434

  日期：2015.6.5

  o- and/or p-naphthoquinone methides (NQMs) can be selectively prepared by the ring opening of 1-(siloxymethyl)-1,4-epoxy-1,4-dihydronaphthalene derivatives based on a substituent effect at the 4 position of the substrates. The 4-alkyl- or silyl-substituted 1-(siloxymethyl)-1,4-epoxy-1,4-dihydronaphthalene was transformed to o-NQM (1-naphthoquinone-2-methide), which underwent Friedel–Crafts 1,4-addition

  邻-和/或对-萘醌甲基化物（NQMs）可通过在1-氨基甲氧基-1,4-甲氧基-1,4-环氧-1,4-二氢萘衍生物的开环作用下的1-（甲硅烷氧基甲基）-1,4-环氧-1,4-二氢萘衍生物的开环来选择性地制备。基材。将4-烷基或甲硅烷基取代的1-（甲硅烷氧基甲基）-1,4-环氧-1,4-二氢萘转化为邻-NQM（1-萘醌-2-甲基），然后进行弗里德尔-克拉夫特工艺1,4 -α，β-不饱和羰基部分的加成得到2-苄基-1-萘酚，作为联芳基甲烷，和[4 + 2]-环加成与二烯亲和剂，得到稠合的杂环芳烃。同时，可通过Friedel-Crafts 1,6-加成p的方法将4-未取代的1-（甲硅烷氧基甲基）-1,4-环氧-1,4-二氢萘转化为相应的4-苄基-1-萘酚。-NQM（1-萘醌-4-甲基化物）是通过1,4-环氧部分的位点选择性开环生成的。此外，将4-（甲硅烷氧基甲基）-（1,4-双（甲硅烷氧基甲基））-1
• Synthesis and antitumor activity of 3-[(methyl)bis(5-trialkylsilyl-furan-2-yl)silyl]propylamines
  作者：L. Ignatovich、V. Romanov、J. Spura、J. Popelis、I. Domracheva、I. Shestakova

  DOI：10.1007/s10593-012-0940-3

  日期：2012.3

  Novel 3-[(methyl)bis(5-trialkylsilylfuran-2-yl)silyl]propylamines have been synthesized by a hydrosilylation reaction of aliphatic and heterocyclic N-allylamines in the presence of the Speier's catalyst. The effects of the structure of the amine and the alkyl substituent at the silicon atom on the cytotoxicity of the compounds have been studied.

  通过在Speier催化剂的存在下脂族和杂环N-烯丙基胺的硅氢加成反应已经合成了新型的3-[（甲基）双（5-三烷基甲硅烷基呋喃-2-基）甲硅烷基]丙胺。研究了硅原子上胺和烷基取代基的结构对化合物细胞毒性的影响。
• Electrophilic Aromatic Substitutions of Silylated Furans and Thiophenes with Retention of the Organosilyl Group
  作者：Mirjam Herrlich、Nathalie Hampel、Herbert Mayr

  DOI：10.1021/ol015810+

  日期：2001.5.1

  [GRAPHICS]isolable in the presence of a proton spongeThe influence of trialkylsilyl groups on the nucleophilic reactivities of furans and thiophenes is determined by kinetic experiments.
• Intramolecular Diels-Alder Reaction of Furans with Allenyl Ethers Followed by Phenylthio and Trialkylsilyl Groups Rearrangement
  作者：Chi-Te Chuang、Chia-Hui Yen、Hsien-Jen Wu

  DOI：10.1002/jccs.199800119

  日期：1998.12

  AbstractA new reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by phenylthio group rearrangement was discovered. Treatment of the propargyl ethers 2a‐c with t‐BuOK in t‐BuOH at 85 ° C gave the phenylthio group rearrangement products 5a‐c and 6a‐c. A reaction involving an intramolecular Diels‐Alder reaction of a furan diene with an allenyl ether dienophile followed by trialkylsilyl group rearrangement is also demonstrated.