1-ethylbut-1-enyl boronic acid | 153748-70-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 1-ethylbut-1-enyl boronic acid
• 英文别名: (3Z)-Hex-3-en-3-ylboronic acid；[(Z)-hex-3-en-3-yl]boronic acid
• CAS: 153748-70-0
• 化学式: C₆H₁₃BO₂
• 分子量: 127.979
• InChiKey: ZZVOVLLPBNLJRC-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-ethylbut-1-enyl boronic acid 在 吡啶 、 copper diacetate 、 sodium sulfate 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 36.0h， 生成 3,4-diethylspiro[4H-1,2-oxazole-5,9'-fluorene]
  参考文献：
  名称：

  N-乙烯基硝基的制备和重排：螺异恶唑啉和芴系的异恶唑的合成

  摘要：

  经由芴酮肟和乙烯基硼酸之间的铜介导的偶联，制备了衍生自芴酮的N-乙烯基硝酮。这些化合物会经历随后的重排和加成反应，这不同于传统的硝酮的[3 + 2]环加成反应性。芴酮N-乙烯基硝酮的热重排生成螺异恶唑啉，而用炔烃处理则得到芴系的异恶唑。讨论了芴酮N-乙烯基硝酮的制备及其局限性及其后续的重排和加成反应。

  DOI：

  10.1021/ol3022885
• 作为产物：
  描述：

  3-己炔 在 水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.08h， 生成 1-ethylbut-1-enyl boronic acid
  参考文献：
  名称：

  通过烯基硼酸的羰基化作用中断的菲舍尔-吲哚中间体

  摘要：

  在铜介导的和铜催化的条件下，已经实现了烯基硼酸与N-芳基苯并异羟肟酸的氧化芳基化，以提供接近的费歇尔-吲哚中间体的途径。据认为，这种转变是通过铜促进的C–O键形成事件继之以[3,3]重排而进行的。描述了该方法的范围并讨论了机械实验。

  DOI：

  10.1021/ol401416r

文献信息

• Diastereoselective Synthesis of Nine-Membered Heterocycles <i>via</i> the Cycloaddition and Sequential Rearrangement of <i>N</i> -Vinyl Nitrones with Isocyanates
  作者：Ning Zou、Ji-Wen Jiao、Yu Feng、Chun-Hua Chen、Cui Liang、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1002/adsc.201700685

  日期：2017.10.25

  A metal‐free construction of highly diastereoselective nine‐membered heterocycles is described via the cycloaddition and rearrangement of N‐vinyl‐α,β‐unsaturated ketonitrones and isocyanates. Notably, the prepared nine‐membered heterocycles afforded 2,3‐dihydropyrrolizines under heating conditions. Mechanistic studies showed that the nine‐membered rings might undergo decarboxylation, isomerization

  通过N-乙烯基-α，β-不饱和酮硝酮和异氰酸酯的环加成和重排描述了高度非对映选择性的九元杂环的无金属结构。值得注意的是，在加热条件下，所制备的九元杂环提供了2,3-二氢吡咯烷酮。机理研究表明，九元环可能会发生脱羧，异构化，氮杂-迈克尔加成和芳构化，从而在一锅反应中得到2,3-二氢吡咯啉。
• Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates
  作者：Gary A. Molander、Carmem R. Bernardi

  DOI：10.1021/jo026236y

  日期：2002.11.1

  that the palladium-catalyzed cross-coupling reaction of air-stable potassium alkenyltrifluoroborates with aryl halides and triflates proceeds readily with good yields. Recent progress in outlining the scope and limitations of such reactions is described herein. The palladium-catalyzed cross-coupling reaction of potassium alkenyltrifluoroborates with aryl and heteroaryl halides and triflates proceeds

  我们以前曾报道过，空气稳定的链烯基三氟硼酸钾与芳基卤化物和三氟甲磺酸酯的钯催化交叉偶联反应容易进行，收率很高。本文描述了概述此类反应的范围和局限性的最新进展。链烯基三氟硼酸钾与芳基和杂芳基卤化物和三氟甲磺酸酯的钯催化交叉偶联反应易于进行，产率中等至优异。烯基的交叉偶联反应通常可以在叔丁基NH 2作为碱的存在下，在i-PrOH-H 2 O中使用2mol％的PdCl 2（dppf）.CH 2 Cl 2作为催化剂来进行。两种配偶体均容忍多种官能团，并且该方法对于烯基三氟硼酸酯原料是立体定向的。
• Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl Bromides
  作者：Gary A. Molander、Luciana A. Felix

  DOI：10.1021/jo050286w

  日期：2005.5.1

  The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes

  描述了使用空气稳定的链烯基三氟硼酸钾作为偶联伴侣的立体选择性合成共轭二烯的方法。钯催化的（E）-和（Z）-烯基三氟硼酸钾与（E）-或（Z）-烯基溴化物的钯催化交叉偶联反应容易进行，产率中等至优异，得到相应的（E，E）- ，（E，Z）-，（Z，E）-或（Z，Z）共轭二烯立体定向。交叉耦合通常可使用5摩尔％的Pd（OAC）的实现2，10摩尔％的PPH 3和Cs的3当量2 CO 3在THF-H 2 O（10∶1）中。两种偶联伙伴均容许多种官能团。
• Preparation and Cycloaddition Reactions of Enantiopure 2-(<i>N-</i>Acylamino)-1,3-dienes for the Synthesis of Octahydroquinoline Derivatives
  作者：Fabrizio Lo Galbo、Ernesto G. Occhiato、Antonio Guarna、Cristina Faggi

  DOI：10.1021/jo0344687

  日期：2003.8.1

  Stille, Suzuki-Miyaura, and Sonogashira cross-coupling reactions were carried out with a glutarimide-derived vinyl phosphate, bearing a chiral auxiliary on the N atom, to prepare enantiopure 2-(N-acylamino)-1,3-dienes as partners in Diels-Alder reactions. The cycloadditions were performed with various dienophiles under thermal conditions, with or without Lewis acids. With maleimides, the preferential formation of endo cycloadducts was observed, whereas with acrylamides the exo approach prevailed. Furthermore, in the latter case, 6-substitued octahydro-quinolinones were obtained in accordance with the predicted regioselectivity. Since diastereopure compounds were in all cases obtained either by chromatography or by crystallization, and because of the easy access to a variety of boronic acids, to be used in the coupling step, this methodology is useful for the short synthesis of differently substituted, enantiopure octahydroquinolinones amenable to further transformation into decahydroquinolines possessing interesting biological activities.
• Dichloroborane–dioxane: an exceptional reagent for the preparation of alkenyl- and alkylboronic acids
  作者：Kanth V.B Josyula、Peng Gao、Chris Hewitt

  DOI：10.1016/j.tetlet.2003.08.086

  日期：2003.10

  Terminal alkynes and alkenes were conveniently hydroborated to the corresponding alkenyl- and alkyldichloroboranes using dichloroborane-dioxane in dichloromethane. These dichloroboranes were hydrolyzed by water to the corresponding alkenyl- and alkylboronic acids in moderate to good yields. With terminal alkenes and alkynes boron was predominantly attached to terminal carbon. Alkynes gave exclusively trans-vinylboronic acids. (C) 2003 Elsevier Ltd. All rights reserved.