tert-butyl(2-iodo-4-methylphenoxy)dimethylsilane | 1318697-60-7

• 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: tert-butyl(2-iodo-4-methylphenoxy)dimethylsilane
• 英文别名: tert-butyl-(2-iodo-4-methylphenoxy)-dimethylsilane
• CAS: 1318697-60-7
• 化学式: C₁₃H₂₁IOSi
• 分子量: 348.299
• InChiKey: OTRWZCLJWTZSFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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-butyl(2-iodo-4-methylphenoxy)dimethylsilane 在 4-二甲氨基吡啶 、 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  手性（无环二氨基卡宾）金（I）催化炔丙酯的动态不对称转化

  摘要：

  报道了手性（无环二氨基卡宾）金（I）配合物催化的高度对映选择性转化。开发了由外消旋苯酚取代的新戊酸炔丙酯对映选择性合成2-取代的新戊酸苯并苯酰的方法。在阳离子金存在下，底物重排得到丙二烯中间体，其环化导致通过动态动力学不对称转化形成对映体富集的产物。

  DOI：

  10.1021/ja205068j
• 作为产物：
  描述：

  对甲酚 在 咪唑 、 chloroamine-T 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl(2-iodo-4-methylphenoxy)dimethylsilane
  参考文献：
  名称：

  One-pot synthesis of 2,2′-bisbenzofurans using cuprous chloride as a catalyst

  摘要：

  A variety of novel 5,5'-disubstituted-2,2'-bisbenzofuran derivatives were synthesized by treatment of 4-substituted-2-(2-trimethylsilylethynyl)phenyl tert-butyldimethylsilyl ether analogues with Cud I as a catalyst in 62-82% isolated yields. This novel strategy provides a straightforward and simple pathway for the preparation of 2,2'-bisbenzofuran derivatives of interest in life and material sciences. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.040

文献信息

• Convenient and Highly Efficient Routes to 2  <i>H</i> ‐Chromene and 4‐Chromanone Derivatives: Iodine‐Promoted and <i>p</i> ‐Toluenesulfonic Acid Catalyzed Cascade Cyclizations of Propynols
  作者：Yi‐Feng Qiu、Yu‐Ying Ye、Xian‐Rong Song、Xin‐Yu Zhu、Fang Yang、Bo Song、Jia Wang、Hui‐Liang Hua、Yu‐Tao He、Ya‐Ping Han、Xue‐Yuan Liu、Yong‐Min Liang

  DOI：10.1002/chem.201406100

  日期：2015.2.16

  A convenient strategy is presented for the easy preparation of a series of 2 H‐chromenes under mild conditions through iodocyclization of readily accessible propynols. In addition, various 4‐chromanones can be synthesized through a p‐toluenesulfonic acid catalyzed cascade cyclization with high efficiency (yields up to 99 %). Our developed reaction systems are proven to have good functional‐group applicability

  提出了一种简便的策略，可以通过容易获得的丙炔醇的碘环化，在温和条件下轻松制备一系列2  H-色烯。此外，可以通过p合成各种4-chromanones甲苯磺酸高效催化级联环化（产率高达99％）。我们开发的反应系统经验证具有良好的官能团适用性，并且可以按比例放大至克数量，并具有令人满意的产率。这些系统还为两种重要的类黄酮骨架提供了新的合成策略，而无需使用昂贵且有毒的金属催化剂。此外，生成的卤化物可进一步用于随后的钯催化的偶联反应中，因此这些化合物可作为潜在的中间体，用于构建某些有价值的药物分子。
• Synthesis of Organophosphorus Compounds through Copper-Catalyzed Annulation Involving C–O and C–P Bond Formations
  作者：Xue-Song Li、Ya-Ping Han、Xin-Yu Zhu、Ming Li、Wan-Xu Wei、Yong-Min Liang

  DOI：10.1021/acs.joc.7b01947

  日期：2017.11.3

  high-efficiency, and atom-economical synthesis of valuable organophosphorus compounds via cascade annulation of propargylic alcohols with diphenylphosphine oxide is described. This protocol, which has a good functional-group compatibility and insensitivity to an ambient atmosphere, provides a simple and direct pathway to the products, organophosphorus compounds, in good yields under mild conditions. The method

  描述了一种新颖的三氟甲磺酸铜（II）催化的高效炔烃与二苯基膦氧化物的级联环氧化合成有价值的有机磷化合物的方法。该方案对环境气氛具有良好的官能团相容性和不敏感性，可在温和条件下以高收率提供一条简单直接的途径通往有机磷化合物产品。该方法可以有效地放大到克级，从而突出了该方法的潜在应用。
• Gold(I)-Catalyzed Domino Cyclization for the Synthesis of Tricyclic Chromones
  作者：Weimin Chen、Henry Wong、Zhiqiang Li、Qingjiang Li、Guo-Kai Liu、Xiao-Shui Peng

  DOI：10.1055/s-0034-1380715

  日期：——

  A simple and efficient method for the synthesis of tricyclic chromones has been developed. In this approach, tricyclic chromones were synthesized from a diverse range of phenols and alkynes through a Sonogashira coupling and subsequent gold-catalyzed intramolecular domino cyclization.

  已开发出一种简单有效的合成三环色酮的方法。在这种方法中，通过 Sonogashira 偶联和随后的金催化分子内多米诺环化，从多种酚类和炔烃合成三环色酮。
• BF₃·Et₂O-Promoted Cleavage of the C_sp–C_sp2 Bond of 2-Propynolphenols/Anilines: Route to C2-Alkenylated Benzoxazoles and Benzimidazoles
  作者：Xian-Rong Song、Yi-Feng Qiu、Bo Song、Xin-Hua Hao、Ya-Ping Han、Pin Gao、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/jo502761x

  日期：2015.2.20

  A novel BF3 center dot Et2O-promoted tandem reaction of easily prepared 2-propynolphenols/anilines and trimethylsilyl azide is developed to give C2-alkenylated benzoxazoles and benzimidazoles in moderate to good yields. Most reactions could be accomplished in 30 min at room temperature. This tandem process involves a C-sp-C-sp2 bond cleavage and a C-N bond formation. Moreover, both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under the mild conditions.
• Rhodium(III)-Catalyzed Direct C-2 Olefination of Unactivated Indoles Utilizing OH/NH₂as Directing Group
  作者：Chen-Yu Tang、Yuan Tao、Xin-Yan Wu、Feng Sha

  DOI：10.1002/adsc.201300930

  日期：2014.2.10

  AbstractOxidative C‐2 olefination of indoles/pyrrole via rhodium(III)‐catalyzed direct CH bond activation is reported. Phenolic OH and aniline NH2 units were revealed to be effective chelating groups to activate the aryl CH bond. The reactions proceeded with excellent selectivity and high functional group tolerance, furnishing 2‐vinylindoles/2‐vinylpyrroles in good yields.magnified image