but-2-ynyloxymethyl phenyl ketone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: but-2-ynyloxymethyl phenyl ketone
• 英文别名: 2-But-2-ynoxy-1-phenylethanone；2-but-2-ynoxy-1-phenylethanone
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: KXIRHFCNUBRELO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  but-2-ynyloxymethyl phenyl ketone 在 bis(1,5-cyclooctadiene)nickel (0) 、 C₂₅H₂₃OP 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  炔酮的高对映选择性镍催化的分子内还原环化

  摘要：

  报道了炔烃的第一个不对称镍催化的分子内还原环化反应。AP-手性单膦和三乙基硅烷分别用作配体和还原剂，以优异的收率和对映选择性形成一系列带有呋喃/吡喃环的叔烯丙基醇。该反应具有广泛的底物范围，并能够有效地合成脱羟基立方体蛋白和手性二苯并环辛二烯骨架。

  DOI：

  10.1002/anie.201410700
• 作为产物：
  描述：

  Ethyl 2-but-2-ynoxyacetate 在 异丙基氯化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 but-2-ynyloxymethyl phenyl ketone
  参考文献：
  名称：

  炔酮的高对映选择性镍催化的分子内还原环化

  摘要：

  报道了炔烃的第一个不对称镍催化的分子内还原环化反应。AP-手性单膦和三乙基硅烷分别用作配体和还原剂，以优异的收率和对映选择性形成一系列带有呋喃/吡喃环的叔烯丙基醇。该反应具有广泛的底物范围，并能够有效地合成脱羟基立方体蛋白和手性二苯并环辛二烯骨架。

  DOI：

  10.1002/anie.201410700

文献信息

• Facile access to 2,2-disubstituted indolin-3-ones via a cascade Fischer indolization/Claisen rearrangement reaction
  作者：Zilei Xia、Jiadong Hu、Yu-Qi Gao、Qizheng Yao、Weiqing Xie

  DOI：10.1039/c7cc03754f

  日期：——

  An efficient approach for the synthesis of 2,2-disubstituted indolin-3-ones is described. From readily accessible aryl hydrazines and allyloxyketones, 2,2-disubstituted indolin-3-ones could be obtained in good to excellent yields under mild reaction conditions via cascade Fischer indolization/Claisen rearrangement process. This protocol provides a facile entry to 2,2-disubstituted indolin-3-ones, which

  描述了一种合成2，2-二取代的吲哚-3-酮的有效方法。从容易获得的芳基肼和烯丙氧基酮，可以通过级联的Fischer吲哚化/ Claisen重排过程，在温和的反应条件下以良好或优异的产率获得2,2-二取代的吲哚-3-酮。该方案为2，2-二取代的吲哚-3-酮提供了简便的方法，该方法已被用于与Ph草碱有关的苯并呋喃二氢吲哚骨架的构建中。
• Rhodium-Catalyzed Asymmetric Tandem Cyclization for Efficient and Rapid Access to Underexplored Heterocyclic Tertiary Allylic Alcohols Containing a Tetrasubstituted Olefin
  作者：Yi Li、Ming-Hua Xu

  DOI：10.1021/ol500993h

  日期：2014.5.16

  Rh-catalyzed asymmetric tandem cyclization of nitrogen- or oxygen-bridged 5-alkynones with arylboronic acids was achieved. The simple catalytic system involving a rhodium(I) complex with readily available chiral BINAP ligand promotes the reaction to proceed in a highly stereocontrolled manner. This protocol provides a very reliable and practical access to a variety of chiral heterocyclic tertiary allylic

  实现了第一个Rh催化的氮或氧桥接的5-炔基与芳基硼酸的不对称串联环化反应。包含铑（I）配合物和易于获得的手性BINAP配体的简单催化体系可促进反应以高度立体可控的方式进行。该方案以高收率和高达99％ee的高对映选择性提供了一种非常可靠和实用的途径，可用于获得具有四取代碳立体中心和全碳四取代烯烃官能度的各种手性杂环叔烯丙基醇。
• Rhodium-Catalyzed Addition-Cyclization Reactions of 5-Yn-1-ones with Arylboronic Acids
  作者：Masahiro Murakami、Tomoya Miura、Masahiko Shimada

  DOI：10.1055/s-2005-863718

  日期：——

  presence of a catalytic amount of rhodium(I) complex having a diolefin ligand to afford 2-alkylidenecyclopentanols through the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond, followed by intramolecular nucleophilic addition of the resulting vinylrhodium(I) species to the carbonyl group.

  5-Yn-1-ones 与芳基硼酸在催化量的具有二烯烃配体的铑 (I) 配合物存在下反应，通过区域选择性加成跨碳-碳三元组的芳基铑 (I) 物质，得到 2-亚烷基环戊醇键，然后将所得乙烯基铑 (I) 物质分子内亲核加成到羰基上。
• Precatalyst‐Enabled Selectivity: Enantioselective NiH‐Catalyzed <i>anti</i> ‐Hydrometalative Cyclization of Alkynones to <i>Endo</i> ‐ and Heterocyclic Allylic Alcohols
  作者：Xiao‐Wen Zhang、Ming‐Hui Zhu、Hai‐Xiang Zeng、Qi‐Yang Li、Wen‐Bo Liu

  DOI：10.1002/anie.202110815

  日期：2021.12.20

  AbstractA highly enantioselective NiH‐catalyzed hydrocyclization of alkynones with unparalleled anti‐ and endocyclic selectivities is described. The choice of the precatalysts has significant influence in tuning the regio‐ and enantioselectivity. Using Ni(OTs)2/Phox as a precatalyst and (EtO)2MeSiH as a hydride source, an array of enantioenriched O‐, N‐, and S‐containing heterocyclic tertiary allylic alcohols are obtained in 24–81 % yields with 80:20–99:1 er. Mechanistic investigations and synthetic application are also carried out. This study represents an efficient access to a set of allylic alcohols that are unable to access by the state‐of‐the‐art coupling reactions.
• Rhodium-catalyzed arylative cyclization of alkynones induced by addition of arylboronic acids
  作者：Tomoya Miura、Masahiko Shimada、Masahiro Murakami

  DOI：10.1016/j.tet.2007.03.025

  日期：2007.7

  Alkynones react with arylboronic acids in the presence of a rhodium(I) catalyst to afford four- and five-membered-ring cyclic alcohols equipped with a tetrasubstituted exocyclic olefin. The cyclic allylic alcohol skeleton is constructed by the carbon-carbon bond formation between the carbonyl group and an alkenylrhodium(I) intermediate formed by the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond. (c) 2007 Elsevier Ltd. All rights reserved.