(26a)-{[1-(3,4-dichlorophenyl)ethenyl]oxy}(trimethyl)silane | 91077-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (26a)-{[1-(3,4-dichlorophenyl)ethenyl]oxy}(trimethyl)silane
• 英文别名: {[1-(3,4-dichlorophenyl)ethenyl]oxy}(trimethyl)silane；α-Trimethylsilyloxy-3,4-dichlorostyrene；Silane, [[1-(3,4-dichlorophenyl)ethenyl]oxy]trimethyl-；1-(3,4-dichlorophenyl)ethenoxy-trimethylsilane
• CAS: 91077-75-7
• 化学式: C₁₁H₁₄Cl₂OSi
• 分子量: 261.223
• InChiKey: LJVCFOBIHFEASD-UHFFFAOYSA-N

物化性质

• 沸点：
  129-130 °C(Press: 8 Torr)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (26a)-{[1-(3,4-dichlorophenyl)ethenyl]oxy}(trimethyl)silane 在 吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三光气 、 间氯过氧苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 Petroleum ether 为溶剂， 反应 44.0h， 生成 7-(4-bromothiophen-2-yl)-10-(3,4-dichlorophenyl)-2,4-dimethyl-8-oxa-2,4-diazaspiro[5.6]dodec-10-ene-1,3,5-trione
  参考文献：
  名称：

  Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

  摘要：

  A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

  DOI：

  10.1021/acs.orglett.0c02508
• 作为产物：
  描述：

  碘代三甲硅烷 、 3,4-二氯苯乙酮 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以96%的产率得到(26a)-{[1-(3,4-dichlorophenyl)ethenyl]oxy}(trimethyl)silane
  参考文献：
  名称：

  Shipov, A. G.; Orlova, N. A.; Savostyanova, I. A., Journal of general chemistry of the USSR, 1989, vol. 59, # 5.2, p. 959 - 971

  摘要：

  DOI：

文献信息

• Catalytic, Enantioselective Alkylation of α-Imino Esters:  The Synthesis of Nonnatural α-Amino Acid Derivatives
  作者：Dana Ferraris、Brandon Young、Christopher Cox、Travis Dudding、William J. Drury、Lev Ryzhkov、Andrew E. Taggi、Thomas Lectka

  DOI：10.1021/ja016838j

  日期：2002.1.1

  Methodology for the practical synthesis of nonnatural amino acids has been developed through the catalytic, asymmetric alkylation of α-imino esters and N,O-acetals by enol silanes, ketene acetals, alkenes, and allylsilanes using chiral transition metal-phosphine complexes as catalysts (1−5 mol %). The alkylation products, which are prepared with high enantioselectivity (up to 99% ee) and diastereoselectivity

  使用手性过渡金属-膦配合物作为催化剂，通过烯醇硅烷、乙烯酮缩醛、烯烃和烯丙基硅烷对 α-亚氨基酯和 N,O-缩醛进行催化不对称烷基化，开发了用于实际合成非天然氨基酸的方法。 1-5 摩尔％）。以高对映选择性（高达 99% ee）和非对映选择性（高达 25:1/anti:syn）制备的烷基化产物是受保护的非天然氨基酸，代表天然产物和药物的潜在前体。烯烃与α-亚氨基酯催化反应的动力学分析被提出以阐明该反应的机理。
• Catalytic, Asymmetric Mannich-Type Reactions of α-Imino Esters Bearing Readily Removable Substituents on Nitrogen
  作者：Yoshitaka Nakamura、Ryosuke Matsubara、Hiroshi Kiyohara、Shū Kobayashi

  DOI：10.1021/ol034717d

  日期：2003.7.1

  [reaction: see text] Catalytic, enantioselective Mannich-type reactions of alpha-imino esters bearing readily removable substituents on nitrogen are described. Several N-carbamate-protected alpha-imino esters, which are readily prepared from 2-bromoglycine esters using a polymer-supported amine, reacted with silicon enolates to afford the desired adducts in high yields with high enantioselectivity

  [反应：见正文]描述了在氮上带有易于除去的取代基的α-亚氨基酯的催化，对映选择性曼尼希型反应。几种由N-氨基甲酸酯保护的α-亚氨基酯易于使用聚合物负载的胺从2-溴甘氨酸酯制备，并与烯醇硅反应，以高收率使用铜（II）-二胺以高对映选择性提供所需的加合物。复杂的。还已经证明了产物胺容易脱保护并转化为游离的α-氨基酸衍生物。
• Catalytic Asymmetric Synthesis of α-Amino Phosphonates Using Enantioselective Carbon−Carbon Bond-Forming Reactions
  作者：Shū Kobayashi、Hiroshi Kiyohara、Yoshitaka Nakamura、Ryosuke Matsubara

  DOI：10.1021/ja048791i

  日期：2004.6.1

  enolates with N-acyl-α-iminophosphonates leading to optically active α-amino phophonates. A copper (II)−diamine complex was shown to be effective in this reaction, and high levels of yield and selectivity were achieved. It is noteworthy that this reaction opens a way to various biologically important, optically active α-amino phosphonate derivatives.

  我们已经开发出硅烯醇化物与 N-酰基-α-亚氨基膦酸酯的高度对映选择性反应，从而产生光学活性的 α-氨基膦酸酯。铜 (II)-二胺络合物在该反应中显示有效，并且实现了高水平的产率和选择性。值得注意的是，该反应为各种具有生物学重要意义的光学活性 α-氨基膦酸酯衍生物开辟了道路。
• 10.1021/acs.joc.4c00310
  作者：Liang, Tongwei、Yuan, Qingjia、Xu, Li、Liu, Jian-Quan、Kärkäs, Markus D.、Wang, Xiang-Shan

  DOI：10.1021/acs.joc.4c00310

  日期：——

  for the intermolecular radical umpolung cross-coupling protocol of silyl enol ethers with activated methylene compounds is disclosed. The protocol exhibits excellent functional group tolerance, enabling the expedient preparation of a variety of tricarbonyl compounds. Preliminary mechanistic investigations suggest that the reaction proceeds through a process involving free radicals in which silver oxide

  公开了用于甲硅烷基烯醇醚与活化的亚甲基化合物的分子间自由基翻转交叉偶联方案的银催化方案。该方案表现出优异的官能团耐受性，能够方便地制备各种三羰基化合物。初步机理研究表明，该反应通过涉及自由基的过程进行，其中氧化银具有双重作用，既充当催化剂又充当碱。
• A topliss tree analysis of the HIV-protease inhibitory activity of 6-phenyl-4-hydroxy-pyran-2-ones
  作者：Bruce A. Steinbaugh、Harriet W. Hamilton、J.V.N. Vara Prasad、Kimberly S. Para、Peter J. Tummino、Donna Ferguson、Elizabeth A. Lunney、C. John Blankley

  DOI：10.1016/0960-894x(96)00180-1

  日期：1996.5

  In a study of 4-hydroxy-pyran-2-ones as possible inhibitors of HIV protease, a series of compounds were synthesized following the Topliss operational scheme for substitution on a phenyl group at the 6 position of the pyrone. In addition, a number of compounds with polar substituents were made. (C) 1996 Elsevier Science Ltd