4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-3-en-2-one | 440084-09-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-3-en-2-one
• 英文别名: 4-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]but-3-en-2-one
• CAS: 440084-09-3
• 化学式: C₁₆H₂₁BO₃
• 分子量: 272.152
• InChiKey: DOPARYWVKNHMSH-UHFFFAOYSA-N

物化性质

• 沸点：
  410.7±28.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-3-en-2-one 、 2-丁炔酸甲酯 在 Pd(OTf)2*2H₂O 、 C₄₆H₄₄O₄P₂ 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以99%的产率得到methyl 3-methyl-1-(2-oxopropyl)-1H-indene-2-carboxylate
  参考文献：
  名称：

  Cationic Palladium(II)-Catalyzed Highly Enantioselective Tandem Reactions of ortho-Boronate-Substituted Cinnamic Ketones and Internal Alkynes: A Convenient Synthesis of Optically Active Indenes

  摘要：

  Cationic palladium(II)-catalyzed tandem reactions of ortho-boronate-substituted cinnamic ketones and internal alkynes to yield optically active indenes were developed in high yields and good enantioselectivities.

  DOI：

  10.1021/ol9001015
• 作为产物：
  描述：

  1-三苯基膦-2-丙酮 、 2-甲酰基苯基硼酸频哪醇酯 以 甲苯 为溶剂， 反应 18.0h， 以72%的产率得到4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-3-en-2-one
  参考文献：
  名称：

  Cationic Palladium(II)-Catalyzed Highly Enantioselective Tandem Reactions of ortho-Boronate-Substituted Cinnamic Ketones and Internal Alkynes: A Convenient Synthesis of Optically Active Indenes

  摘要：

  Cationic palladium(II)-catalyzed tandem reactions of ortho-boronate-substituted cinnamic ketones and internal alkynes to yield optically active indenes were developed in high yields and good enantioselectivities.

  DOI：

  10.1021/ol9001015

文献信息

• Synthesis of 6-Substituted Phenanthridine Derivatives by Palladium-Catalysed Domino Suzuki-Miyaura/Aza-Michael Reactions
  作者：Xiaobo Bao、Wei Yao、Qihua Zhu、Yungen Xu

  DOI：10.1002/ejoc.201402913

  日期：2014.11

  An efficient method for the synthesis of 6-substituted phenanthridine derivatives has been developed through a one-pot process involving a sequence of palladium-catalysed Suzuki–Miyaura reaction followed by intramolecular aza-Michael addition. This method is applicable to the synthesis of a wide range of substituted phenanthridines from simple substrates.

  已经通过一锅法开发了一种合成 6-取代菲啶衍生物的有效方法，该方法涉及一系列钯催化的 Suzuki-Miyaura 反应，然后是分子内 aza-Michael 加成。该方法适用于从简单底物合成多种取代菲啶。
• Synthesis of Indenyl Triazenes by Rhodium-Catalyzed Annulation Reactions
  作者：Carl T. Bormann、Florian G. Abela、Rosario Scopelliti、Farzaneh Fadaei-Tirani、Kay Severin

  DOI：10.1002/ejoc.202000195

  日期：2020.4.16

  Rh‐catalyzed [3+2] annulation reactions of arylboronic acid derivatives and alkynyl triazenes, which provide access to functionalized indenyl triazenes, are described. The regioselectivity of the annulations is mostly high, but strongly dependent on the substituents on the alkyne

  描述了芳基硼酸衍生物和炔基三氮烯的Rh催化的[3 + 2]环化反应，提供了功能化的茚基三氮烯的通道。环的区域选择性大部分较高，但强烈取决于炔烃上的取代基
• Rhodium-Catalyzed Asymmetric Annulation of Unactivated Alkynes with 3-(<i>ortho</i>-Boronated Aryl) Conjugated Enones: Enantioselective Synthesis of 2,3-Disubstituted Indenes
  作者：Yu Sun、Jiayu Pan、Xiuqi Wang、Xiaoli Bu、Mengtao Ma、Fei Xue

  DOI：10.1021/acs.joc.2c02957

  日期：2023.5.5

  A rhodium-catalyzed tandem arylation/cyclization reaction of 3-(ortho-boronated aryl) conjugated enones with unactivated alkynes is reported. By using a rhodium(I)/chiral-diene complex as the catalyst, the protocol was processed smoothly to provide various 2,3-disubstituted indene compounds in high yields with excellent regioselectivities and enantioselectivities. The approach outlined herein is appealing

  报道了 3-（邻位硼化芳基）共轭烯酮与未活化炔烃的铑催化串联芳基化/环化反应。通过使用铑 (I)/手性二烯配合物作为催化剂，该方案顺利进行，以高收率提供具有出色区域选择性和对映选择性的各种 2,3-二取代茚化合物。本文概述的方法很有吸引力，因为简单的二芳基炔烃、二烷基炔烃和烷基（芳基）炔烃是起始材料。
• Rhodium-Catalyzed Annulation of Ynamides with Bifunctional Arylboron Reagents
  作者：Benoit Gourdet、Mairi E. Rudkin、Hon Wai Lam

  DOI：10.1021/ol100769p

  日期：2010.6.4

  Annulation of ynamides with arylboronic acids or esters containing an electrophilic functional group at the ortho-position proceeds under the action of rhodium catalysis to generate 2-amidoindenols or 2-amidoindenes, usually with good regioselectivity,