5-[Tert-butyl(dimethyl)silyl]oxy-3-methylpent-1-yn-3-ol | 885655-04-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[Tert-butyl(dimethyl)silyl]oxy-3-methylpent-1-yn-3-ol
• CAS: 885655-04-9
• 化学式: C₁₂H₂₄O₂Si
• 分子量: 228.407
• InChiKey: FXXAHXREUJJDAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[Tert-butyl(dimethyl)silyl]oxy-3-methylpent-1-yn-3-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦氯金 吡啶 、 4-二甲氨基吡啶 、 silver hexafluoroantimonate 、 copper(l) iodide 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 3a,8-dimethyl-3b-phenyl-3,3a,3b,4,5,6,7,8a-octahydro-2H-1-oxa-cyclopenta[a]indene
  参考文献：
  名称：

  金（I）催化的功能化环戊二烯的合成。

  摘要：

  DOI：

  10.1002/anie.200604006
• 作为产物：
  描述：

  4-[(叔-丁基二甲基硅烷基)氧基]丁烷-2-酮 、 三甲基乙炔基硅 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-[Tert-butyl(dimethyl)silyl]oxy-3-methylpent-1-yn-3-ol
  参考文献：
  名称：

  Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes

  摘要：

  By using designed biphenyl-2-ylphosphines functionalized with a remote basic groups as ligands, N-alkynyl-o-nosylamides are directly converted to (1E,3E)-1-amido-1,3-dienes with excellent diastereoselectivities under gold catalysis. With allenamides as substrates, the gold-catalyzed isomerizations are high yielding and applicable to a broad substrate scope including various nitrogen protecting groups and exhibit unprecedented (3E)-selectivities for the distal C-C double bond and good regioselectivities. Combining this gold catalysis with one-pot Diels-Alder reactions leads to rapid assembly of valuable bicyclic compounds.

  DOI：

  10.1021/acs.orglett.7b02624

文献信息

• ACETYLENE ALCOHOL AND METHOD FOR PREPARING THE SAME
  申请人：Koike Norivuki

  公开号：US20060100454A1

  公开（公告）日：2006-05-11

  An acetylene alcohol represented by the following formula, wherein R 1 represents a monovalent hydrocarbon radical having 4 to 10 carbon atoms with the carbon atom bonded to the silicon atom being a tertiary carbon, R 2 and R 3 each represents a monovalent group selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and a fluorinated group represented by the formula, Rf-Q-, wherein Rf is a linear or branched perfluoroalkyl group having 3 to 100 carbon atoms which may be interrupted by one or more ether bonds, and Q is a divalent group having 2 to 10 carbon atoms which may be interrupted by one or more nitrogen, oxygen, or sulfur atoms, and n is zero or 1.

  一种乙炔醇，其化学式如下，其中R1代表具有4至10个碳原子的一价烃基，其中与硅原子结合的碳原子是三级碳，R2和R3分别代表由1至4个碳原子的烷基和由以下公式表示的氟化基所选的一价基团，Rf-Q-，其中Rf是具有3至100个碳原子的线性或支链全氟烷基，可以通过一个或多个醚键中断，Q是具有2至10个碳原子的二价基团，可以通过一个或多个氮、氧或硫原子中断，n为零或1。
• LiO^<i>t</i>Bu-Promoted <i>trans</i>-Stereoselective and β-Regioselective Hydroboration of Propargyl Alcohols
  作者：Xia Tian、Yu-Kun Zhang、Ya-Xin You、Jian-Rong Han、Qiu-Shi Cheng、Shi-Ming Fan、Di-Di Chen、Ting-Ting Wang、Shouxin Liu、Wei Su

  DOI：10.1021/acs.orglett.3c02411

  日期：2023.9.1

  (Bpin)2 as the boron reagent in dimethyl sulfoxide at room temperature. Both terminal and internal propargyl alcohols with diverse structures and functional groups underwent the transformation smoothly to produce β-Bpin-substituted (E)-allylic alcohols, of which the synthetic potentials were demonstrated by the downstream conversions of boronate, alkenyl, and hydroxyl groups.

  在室温下，仅以 LiOtBu 为碱，以 （Bpin）2 为硼试剂，即可在室温下在二甲基亚砜中实现方便高效的炔丙醇反式立体选择性和β区选择性硼氢化。具有不同结构和官能团的末端和内部炔丙醇都顺利地发生转化，生成 β-Bpin 取代 （E）-烯丙醇，其中合成潜力通过硼酸盐、烯基和羟基的下游转化得到证明。
• Gold(I)-Catalyzed Synthesis of Functionalized Cyclopentadienes
  作者：Jun Hee Lee、F. Dean Toste

  DOI：10.1002/anie.200604006

  日期：2007.1.29
• Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes
  作者：Xingguang Li、Zhixun Wang、Xu Ma、Pei-nian Liu、Liming Zhang

  DOI：10.1021/acs.orglett.7b02624

  日期：2017.11.3

  By using designed biphenyl-2-ylphosphines functionalized with a remote basic groups as ligands, N-alkynyl-o-nosylamides are directly converted to (1E,3E)-1-amido-1,3-dienes with excellent diastereoselectivities under gold catalysis. With allenamides as substrates, the gold-catalyzed isomerizations are high yielding and applicable to a broad substrate scope including various nitrogen protecting groups and exhibit unprecedented (3E)-selectivities for the distal C-C double bond and good regioselectivities. Combining this gold catalysis with one-pot Diels-Alder reactions leads to rapid assembly of valuable bicyclic compounds.