{2-[4-fluoro-2-(methoxymethyl)phenyl]ethynyl}trimethylsilane | 842167-55-9

• 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: {2-[4-fluoro-2-(methoxymethyl)phenyl]ethynyl}trimethylsilane
• 英文别名: ((4-fluoro-2-(methoxymethyl)phenyl)ethynyl)trimethylsilane；2-[4-fluoro-2-(methoxymethyl)phenyl]ethynyl-trimethylsilane
• CAS: 842167-55-9
• 化学式: C₁₃H₁₇FOSi
• 分子量: 236.361
• InChiKey: ZNUOKHIGEBXKBA-UHFFFAOYSA-N

物化性质

• 沸点：
  253.3±40.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  {2-[4-fluoro-2-(methoxymethyl)phenyl]ethynyl}trimethylsilane 在 盐酸 、 sodium tetrahydroborate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氯化亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 4.0~160.0 ℃ 、6.89 MPa 条件下， 反应 32.5h， 生成 ethyl 6-fluoro-4-(methoxymethyl)-2,3-dihydro-1H-indene-1-carbimidate hydrochloride
  参考文献：
  名称：

  A concise synthesis of chiral indanes as α 1A adrenoceptor partial agonists

  摘要：

  The synthesis of a series of chiral indanes with reported am partial agonist activity is outlined, applying a rhodium catalysed cyclisation for template construction. This method was extended to the asymmetric synthesis of lead compound PF-03774076 (1) which was prepared on >20 g scale in seven steps. Highlights include Rh-mediated cyclocarbonylation and an asymmetric alkene hydrogenation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.004
• 作为产物：
  描述：

  1-溴-4-氟-2-(甲氧基甲基)苯 在 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 {2-[4-fluoro-2-(methoxymethyl)phenyl]ethynyl}trimethylsilane
  参考文献：
  名称：

  Copper-Catalyzed Allylations of Zirconocene Intermediates Generated from o-Alkenyl or o-Alkynylbenzyl Ether Derivatives and Zirconocene−Butene Complex

  摘要：

  o-Alkenyl or alkynyl benzylzirconocene intermediate, which was readily generated by the reaction of 2-alkoxymethyl-styrene or 2-alkoxymethyl-1-(trimethylsilylethynyl)-benzene derivative with zirconocene-butene complex (Negishi reagent, "Cp2Zr"), reacted with allyl or propargyl halides in the presence of a catalytic amount of CuCl to give allylation or allenylation products. Conversion to Dane's diene, which is a key intermediate for estrone synthesis, was efficiently carried out by enyne olefin metathesis of the allylation products.

  DOI：

  10.1021/jo048860b

文献信息

• Novel 2-imidazoles as potent, selective and CNS penetrant α1A adrenoceptor partial agonists
  作者：Lee R. Roberts、Justin Bryans、Kelly Conlon、Gordon McMurray、Alan Stobie、Gavin A. Whitlock

  DOI：10.1016/j.bmcl.2008.10.066

  日期：2008.12

  A novel series of central nervous system (CNS) penetrant indane 2-imidazoles have been identified as potent, partial agonists of the alpha(1A) adrenergic receptor, having good selectivity over the alpha(1B), alpha(1D) and alpha(2) sub-types. A key structural motif to impart selectivity is a methylene spacer between the indane and a pendant substituent, which includes heterocycles, sulphones and ethers. Introduction of an ortho-halogen to this group led to a lowering of intrinsic efficacy (E-max). (C) 2008 Elsevier Ltd. All rights reserved.