tert-butyldimethyl[[1-(2-(phenylethynyl)phenyl)vinyl]oxy]silane | 371964-02-2

• 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: tert-butyldimethyl[[1-(2-(phenylethynyl)phenyl)vinyl]oxy]silane
• 英文别名: Tert-butyl-dimethyl-[1-[2-(2-phenylethynyl)phenyl]ethenoxy]silane
• CAS: 371964-02-2
• 化学式: C₂₂H₂₆OSi
• 分子量: 334.533
• InChiKey: AJHVSTVMBOKORZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• 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：

  tert-butyldimethyl[[1-(2-(phenylethynyl)phenyl)vinyl]oxy]silane 在 cesium acetate 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以25%的产率得到1-(2-(苯基乙炔基)苯基)乙酮
  参考文献：
  名称：

  炔酮的化学和区域选择性催化剂控制的碳环化：1-茚满酮和1-萘酚的快速合成

  摘要：

  提出了一种由催化剂控制的2-炔基芳基酮的分子内碳环化反应。下铑（III）催化，1-茚满酮是通过5-形成外切-挖独家化疗选择性，区域选择性和立体选择性carbocyclizations。当由铜催化的（I），1-萘酚通过6-得到内型-挖独家化疗和区域选择性carbocyclizations。

  DOI：

  10.1002/chem.201901860
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 1-(2-(苯基乙炔基)苯基)乙酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyldimethyl[[1-(2-(phenylethynyl)phenyl)vinyl]oxy]silane
  参考文献：
  名称：

  Transition-metal-promoted 6-endo-dig cyclization of aromatic enynes: rapid synthesis of functionalized naphthalenes

  摘要：

  Transition-metal-mediated cyclization of aromatic enynes provides high yields of substituted naphthalene compounds. The reaction can tolerate a wide range of substituents on both the olefin and the alkyne. The most useful catalysts were found to be [Rh(CO)(2)Cl](2), PdCl2 and PtCl2. In addition, a facile silyl migration occurs when the acetylene is substituted with a triorganosilyl group affording 4-silyl-naplithalenes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01146-7

文献信息

• Gold(I)-Catalyzed Regioselective Inter-/Intramolecular Addition Cascade of Di- and Triynes for Direct Construction of Substituted Naphthalenes
  作者：Saori Naoe、Yamato Suzuki、Kimio Hirano、Yusuke Inaba、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo300771f

  日期：2012.6.1

  intermolecular addition–intramolecular carbocyclization reaction of dialkynylbenzenes was developed. In this reaction, regioselective addition of an external nucleophile toward the terminal alkyne and subsequent 6-endo-dig cyclization proceeded to give the 1,3-disubstituted naphthalenes in good yields. The direct synthesis of disubstituted chrysenes via a gold-catalyzed addition and double cyclization cascade

  开发了金催化的二炔基苯的级联分子间加成-分子内碳环化反应。在该反应中，进行了向末端炔烃的区域亲核试剂的区域选择性加成和随后的6 -endo-dig环化，从而以良好的产率得到了1，3-二取代的萘。还实现了通过使用三炔类底物的金催化加成和双环化级联反应直接合成二取代的chrysenes。
• Silver(I) versus Gold(I) Catalysis in Benzannulation Reaction: A Versatile Access to Acridines
  作者：Philippe Belmont、Thomas Godet

  DOI：10.1055/s-2008-1078178

  日期：——

  catalytic amounts of gold and/or silver salts, the reaction of silyl enol ethers onto alkynes occurs under mild conditions to produce the corresponding polycyclic aromatic systems (acridine, quinoline or naphthalene cores) in good to high yields. Among the catalysts investigated, AgOTf has been chosen as a general catalyst for this reaction which likely proceeds through silver(I) activation of the alkynyl

  描述了银/金催化的苯并环化反应。在催化量的金和/或银盐的存在下，甲硅烷基烯醇醚与炔烃的反应在温和条件下发生，以良好到高产率产生相应的多环芳族系统（吖啶、喹啉或萘核）。在所研究的催化剂中，已选择 AgOTf 作为该反应的通用催化剂，该反应可能通过银（I）活化炔基部分进行，导致随后的环异构化反应。
• Chemo‐ and Regioselective Catalyst‐Controlled Carbocyclization of Alkynyl Ketones: Rapid Synthesis of 1‐Indanones and 1‐Naphthols
  作者：Liangliang Song、Guilong Tian、Erik V. Van der Eycken

  DOI：10.1002/chem.201901860

  日期：2019.6.7

  A catalyst‐controlled intramolecular carbocyclization of 2‐alkynyl aryl ketones is presented. Under rhodium(III) catalysis, 1‐indanones are formed through 5‐exo‐dig carbocyclizations with exclusive chemo‐, regio‐ and stereoselectivity. When catalyzed by copper(I), 1‐naphthols are obtained through 6‐endo‐dig carbocyclizations with exclusive chemo‐ and regioselectivity.

  提出了一种由催化剂控制的2-炔基芳基酮的分子内碳环化反应。下铑（III）催化，1-茚满酮是通过5-形成外切-挖独家化疗选择性，区域选择性和立体选择性carbocyclizations。当由铜催化的（I），1-萘酚通过6-得到内型-挖独家化疗和区域选择性carbocyclizations。
• Transition-metal-promoted 6-endo-dig cyclization of aromatic enynes: rapid synthesis of functionalized naphthalenes
  作者：John W Dankwardt

  DOI：10.1016/s0040-4039(01)01146-7

  日期：2001.8

  Transition-metal-mediated cyclization of aromatic enynes provides high yields of substituted naphthalene compounds. The reaction can tolerate a wide range of substituents on both the olefin and the alkyne. The most useful catalysts were found to be [Rh(CO)(2)Cl](2), PdCl2 and PtCl2. In addition, a facile silyl migration occurs when the acetylene is substituted with a triorganosilyl group affording 4-silyl-naplithalenes. (C) 2001 Elsevier Science Ltd. All rights reserved.