trimethyl(pent-2-en-3-yloxy)silane | 40911-69-1

• 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: trimethyl(pent-2-en-3-yloxy)silane
• 英文别名: 2-Trimethylsiloxy-2-penten；2-Trimethylsilyloxy-2-pentene；trimethyl(pent-2-en-2-yloxy)silane
• CAS: 40911-69-1
• 化学式: C₈H₁₈OSi
• 分子量: 158.316
• InChiKey: ZZEYTWGUPVMOKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trimethyl(pent-2-en-3-yloxy)silane 、 4-methoxy-1-(4-methoxyphenyl)-3,4-dimethylpent-1-yn-3-yl acetate 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 硝基甲烷 为溶剂， 反应 0.08h， 以86%的产率得到2-ethyl-4-(4-methoxyphenyl)-3-methyl-5-(3-methylbut-2-en-2-yl)-furan
  参考文献：
  名称：

  三氟甲磺酸铋（III）催化合成2-烯基呋喃

  摘要：

  标题化合物的汇集合成报道，其依赖于一个连续的2重S Ñ在甲氧基取代的丙炔乙酸盐'型取代反应。呋喃C3-C4键大概是通过甲硅烷基烯醇醚攻击炔丙基阳离子中间体而建立的。产生的α-甲氧基烯丙基被分子内取代，通过取代甲氧基基团（形成OC 2键）导致环化并同时形成环外烯烃双键。尽管条件相对温和，但反应在5分钟内完成。

  DOI：

  10.1021/jo5009993
• 作为产物：
  描述：

  2-戊酮 在 magnesium bis(hexamethyldisilazide) 作用下， 以 乙二醇二甲醚 为溶剂， 生成 (1-pentenyl-2-oxy)trimethylsilane 、 trimethyl(pent-2-en-3-yloxy)silane 、 6-Methyl-6-trimethylsilyloxynonan-4-one
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Silyl Enol Ethers Using a New Base Electrogenerated from Hexamethyldisilazane

  摘要：

  The hexamethyldisilazane magnesium salt, a new base readily electrogenerated in an undivided cell fitted with a sacrificial magnesium anode, using a normally equilibrating medium (DME/15% vol HMPA mixture), exhibited a surprising regioselectivity leading to the less highly substituted silyl enol ethers from unsymmetrical ketones. This regioselectivity was not temperature dependent, but was strongly dependent on the nature and proportions of the solvent/cosolvent mixture. Moreover, the reaction was different in pure NMP, and exclusively afforded, from 2-pentanone, the new silylated aldol (56% yield) which resulted from the condensation of the less highly substituted enolate with the ketone.

  DOI：

  10.1021/jo960493j

文献信息

• Mannich Reaction of Imines and Silyl Enol Ethers Induced by Radical Cation Salts: Synthesis of β-Amino Ketones
  作者：Xiao-dong Jia、Xi-cun Wang、Wen-juan Wang、Cong-de Huo、Zheng-jun Quan、Yan Ren

  DOI：10.1055/s-0030-1259036

  日期：2010.12

  Mannich reaction of imines and sily enol ethers induced by radical cation salts was investigated and a series of β-amino ketones were synthesized. Reverse diastereoselectivity was obtained in the reactions of imines and silyl enol ethers of pentan-2-one and pentan-3-one, respectively, which was rationalized by quantum mechanical calculations. A single electron-transfer mechanism was proposed in which

  研究了自由基阳离子盐诱导亚胺与甲硅烷基烯醇醚的曼尼希反应，合成了一系列β-氨基酮。分别在pentan-2-one和pentan-3-one的亚胺和甲硅烷基烯醇醚的反应中获得了反向非对映选择性，这通过量子力学计算得到了合理化。提出了一种单一的电子转移机制，其中亚胺自由基阳离子在这种转变中充当亲电子物种。
• Photochemical Reaction of 2,3-Dichloro-1,4-naphthoquinone with Enol Silyl Ethers
  作者：Kazuhiro Maruyama、Seiji Tai、Hiroshi Imahori

  DOI：10.1246/bcsj.59.1777

  日期：1986.6

  2-Oxoalkylated 1,4-naphthoquinones were obtained in the photochemical reactions of 2,3-dichloro-1,4-naphthoquinone with 2-trimethylsiloxy-1-alkenes. Application of this method afforded a wide variety of functionalized 2-oxoalkylated 1,4-naphthoquinones. The photochemical reactions of 2,3-dichloro-1,4-naphthoquinone with 1-alkyl-2-(trimethylsiloxy)ethylenes gave naphthol derivatives. However, 1,1-d

  2-氧烷基化的 1,4-萘醌是在 2,3-二氯-1,4-萘醌与 2-三甲基甲硅烷氧基-1-烯烃的光化学反应中获得的。该方法的应用提供了多种功能化的 2-氧代烷基化 1,4-萘醌。2,3-二氯-1,4-萘醌与1-烷基-2-(三甲基甲硅烷氧基)乙烯的光化学反应得到萘酚衍生物。然而，1,1-二烷基-2-(三甲基甲硅烷氧基)乙烯没有产生任何产物。
• Ketone derivatives and medical application thereof
  申请人：Toray Industries, Inc.

  公开号：US06215016B1

  公开（公告）日：2001-04-10

  The present invention relates to ketone derivatives represented by the following formula and medical agents containing the ketone derivatives or pharmacologically acceptable salts thereof as an active ingredient, and in particular, relates to a hematopoietic agent; it is shown that the present invention increases blood cells, such as platelets, white blood cells, and red blood cells, and is effective in preventing and treating cytopenia caused by cancer chemotherapy, radiation therapy, and the like.

  本发明涉及以下式表示的酮衍生物及含有该酮衍生物或其药学上可接受的盐为活性成分的医药制剂，特别是涉及一种造血剂；本发明表明该制剂可提高血小板、白细胞和红细胞等血细胞数量，对于预防和治疗由癌症化疗、放疗等引起的细胞减少症具有良好的疗效。
• Enantioselective Construction of Highly Functionalized Indoloquinolizines—congeners to Polycyclic Indole Alkaloids
  作者：Ralf Lock、Herbert Waldmann

  DOI：10.1002/chem.19970030122

  日期：1997.1

  AbstractIndolo[2,3‐a]quinolizines have been prepared in enantiomerically pure form by a very short and efficient synthetic sequence consisting of a) formation of imines of tryptophan esters, b) their enantioselective reaction with substituted silyloxydienes mediated by a chiral or an achiral boron Lewis acid, and c) subsequent ring closure initiated by conversion of the generated vinylogous amides into vinylogous imidoyl chlorides. With this strategy various substituents can be incorporated directly into the 1‐position of the heterocyclic framework of complex indole alkaloids by the choice of an appropriate silyloxydiene, so that subsequent derivatization of the alkaloid precursor at this position is rendered unnecessary.