2-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)phenol | 1374575-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)phenol
• 英文别名: 2-[1-Hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl]phenol；2-(1-hydroxy-3-trimethylsilylprop-2-ynyl)phenol
• CAS: 1374575-83-3
• 化学式: C₁₂H₁₆O₂Si
• 分子量: 220.343
• InChiKey: VHZAWCYFGSHXAP-UHFFFAOYSA-N

物化性质

• 沸点：
  333.2±32.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)phenol 在 potassium phosphate 、 copper(l) iodide 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 2-亚甲基-2,3-二氢-1-苯并呋喃-3-醇
  参考文献：
  名称：

  一种新的铜（I）催化环醚化/酸催化烯丙基亲核取代，用于一锅法合成 2-取代苯并呋喃

  摘要：

  已开发出一种新的铜 (I) 催化环醚化，然后进行酸催化烯丙基亲核取代，用于一锅法合成 2-取代苯并呋喃。这种一锅法反应在极其温和的条件下使用简单且廉价的催化剂有效进行，以良好到优异的产率提供多种取代的苯并呋喃。

  DOI：

  10.1055/s-0031-1290767
• 作为产物：
  描述：

  2-溴苯甲醛二乙缩醛 在 盐酸 、 bis(1,5-cyclooctadiene)nickel (0) 、 正丁基锂 、 双氧水 、 potassium hydrogencarbonate 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 14.5h， 生成 2-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)phenol
  参考文献：
  名称：

  Highly Efficient Activation of Organosilanes with η²-Aldehyde Nickel Complexes: Key for Catalytic Syntheses of Aryl-, Vinyl-, and Alkynyl-Benzoxasiloles

  摘要：

  An eta(2)-aldehyde nickel complex was utilized as an effective activator for an organosilane in order to generate a hypervalent silicate reactant for the first time. This method was successfully applied to the highly efficient syntheses of 3-aryl-, vinyl-, and alkynyl-2,1-benzoxasiloles from benzaldehydes with aryl-, vinyl-, and alkynylsilyl groups at the ortho position. Initial mechanistic studies revealed that an intermolecular aryl transfer process was involved in the reaction mechanism. The formation of an eta(2)-aldehyde complex was directly confirmed by NMR.

  DOI：

  10.1021/ja510089c

文献信息

• Propargylation of CoQ0 through the Redox Chain Reaction
  作者：Robert Pawlowski、Maciej Stodulski、Jacek Mlynarski

  DOI：10.1021/acs.joc.1c02685

  日期：2022.1.7

  propargylation of CoQ0 is described by employing the cooperative effect of Sc(OTf)3 and Hantzsch ester. It is suggested to work through the redox chain reaction, which involves hydroquinone and dimeric propargylic moiety intermediates. A broad range of propargylic alcohols can be converted into the appropriate derivatives of CoQ0 containing triple bonds in good to excellent yields. The mechanism of the given

  通过使用 Sc(OTf) 3和 Hantzsch 酯的协同作用，描述了 CoQ0 的有效催化炔丙基化。建议通过氧化还原链反应进行，该反应涉及氢醌和二聚炔丙基部分中间体。广泛的炔丙醇可以转化为合适的含有三键的 CoQ0 衍生物，产率从良好到极好。还讨论了给定转换的机制。
• Copper(I)-Catalyzed Hydroalkoxylation/Hydrogen-Bonding-Induced Asymmetric Hetero-Diels-Alder Cycloaddition Cascade: An Approach to Aromatic Spiroketals
  作者：Xin Li、Jijun Xue、Chusheng Huang、Ying Li

  DOI：10.1002/asia.201101056

  日期：2012.5

  One thing leads to another: Bis(benzannelated) 5,6‐spiroketal skeletons can be constructed by an efficient cascade process involving an unprecedented CuI‐catalyzed intramolecular alkyne hydroalkoxylation and an asymmetric hetero‐Diels–Alder cycloaddition. The method yields a series of diversely functionalized spiroketals from two readily available open‐chained starting materials in good yields and

  一件事导致另一件事：可以通过有效的级联过程，包括前所未有的Cu I催化的分子内炔烃加氢烷氧基化和不对称杂Diels-Alder环加成反应，构建双（苯甲酰化）5,6-螺酮骨架。该方法可从两种容易获得的开链起始原料中以高收率和出色的非对映选择性产生一系列功能多样的螺缩酮。
• A New Copper(I)-Catalyzed Cycloetherification/Acid-Catalyzed Allylic Nucleophilic Substitution for One-Pot Synthesis of 2-Substituted Benzofurans
  作者：Jijun Xue、Ying Li、Xin Li、Rui Chen

  DOI：10.1055/s-0031-1290767

  日期：2012.4

  A new copper(I)-catalyzed cycloetherification followed by an acid-catalyzed allylic nucleophilic substitution have been developed for the one-pot synthesis of 2-substituted benzofurans. This one-pot reaction proceeds efficiently under extremely mild conditions with simple and inexpensive catalysts, providing diversely substituted benzofurans in good to excellent yields.

  已开发出一种新的铜 (I) 催化环醚化，然后进行酸催化烯丙基亲核取代，用于一锅法合成 2-取代苯并呋喃。这种一锅法反应在极其温和的条件下使用简单且廉价的催化剂有效进行，以良好到优异的产率提供多种取代的苯并呋喃。
• Simultaneous Generation and Subsequent Cycloaddition of <i>ortho</i> -Quinonemethides and Cyclic Enecarbamates Promoted by a Gold/Lewis Acid Catalytic System
  作者：Patricia Fernández、Pedro Alonso、Francisco J. Fañanás、Félix Rodríguez

  DOI：10.1002/ejoc.201800679

  日期：2018.8.7

  A gold/BF3 catalytic system promotes the transformation of simple 3‐butynamines and 2‐(hydroxymethyl)phenol derivatives into cyclic enamines and ortho‐quinone methide derivatives. The subsequent formal [4+2]‐cyclization reaction between these two intermediates gives rise to hexahydrochromeno[2,3‐b]pyrrole derivatives.

  金/ BF 3催化体系促进简单的3-丁炔胺和2-（羟甲基）苯酚衍生物转化为环烯胺和邻醌甲基化物衍生物。这两个中间体之间随后的正式的[4 + 2]-环化反应产生了六氢色素[2,3- b ]吡咯衍生物。
• Catalytic Asymmetric Cycloaddition of In Situ-Generated <i>ortho</i> -Quinone Methides and Azlactones by a Triple Brønsted Acid Activation Strategy
  作者：Xiao-Ye Yu、Jia-Rong Chen、Qiang Wei、Hong-Gang Cheng、Zhi-Cheng Liu、Wen-Jing Xiao

  DOI：10.1002/chem.201601227

  日期：2016.5.10

  A convergent and highly stereoselective [4+2] cycloaddition of in situ‐generated ortho‐Quinone methides (o‐QMs) and azlactone enols has been successfully developed through a triple Brønsted acid catalysis strategy. This protocol provides an efficient and mild access to various densely functionalized dihydrocoumarins bearing adjacent quaternary and tertiary stereogenic centers in high yields with excellent

  通过三重布朗斯台德酸催化策略成功开发了原位生成的邻醌-甲基醌（o- QMs）和氮杂内酯烯醇的会聚且高度立体选择性的[4 + 2]环加成反应。该方案可以高效，温和地获得各种高密度功能化的双氢香豆素，这些双氢香豆素具有很高的非对映选择性和对映选择性，可高产地毗邻相邻的季铵和叔立体异构中心。