cis-1-propenylboronic acid | 6336-44-3

• 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: cis-1-propenylboronic acid
• 英文别名: cis-propenylboronic acid；(Z)-Prop-1-en-1-ylboronic acid；[(Z)-prop-1-enyl]boronic acid
• CAS: 6336-44-3
• 化学式: C₃H₇BO₂
• 分子量: 85.8984
• InChiKey: CBMCZKMIOZYAHS-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.43
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• 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：

  cis-1-propenylboronic acid 、 1-(4-喹啉基)甲胺 在 trans-PdBr(N-Succ)(PPh₃)2 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以91%的产率得到2-[(Z)-1-propenyl]-2-cyclohexen-1-one
  参考文献：
  名称：

  Simple Palladium(II) Precatalyst for Suzuki−Miyaura Couplings:  Efficient Reactions of Benzylic, Aryl, Heteroaryl, and Vinyl Coupling Partners

  摘要：

  trans-PdBr(N-Succ)(PPh3)(2) (1) is a universally effective precatalyst for Suzuki-Miyaura cross-couplings of benzylic halides with aryl- or heteroarylboronic acids. Substituted aryl halides and halogenated cyclic enones can be cross-coupled with aryl- or vinylboronic acids in excellent yields. Catalyst recycling is also demonstrated.

  DOI：

  10.1021/ol702291r
• 作为产物：
  描述：

  硼酸三异丙酯 、 (E)-propenyl lithium 在 氮气 、 氯化铵 、 盐酸 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 cis-1-propenylboronic acid
  参考文献：
  名称：

  Enantioselective syn and anti Homocrotylation of Aldehydes: Application to the Formal Synthesis of Spongidepsin

  摘要：

  Whereas crotylboration has been a useful method for synthesis of stereochemically complex products, we have shown that homocrotylboration can be achieved with cyclopropanated crotylation reagents, and that the stereo-selectivity of the reaction can be predicted by analogous models. This paper presents a full account of this work, including the first examples of asymmetric anti homocrotylation. The scope of this reaction is demonstrated with highly enantioselective homocrotylation of both aliphatic and aromatic aldehydes, as well as double diastereoselection studies. An application of the synthesis of the marine natural product spongidepsin is presented, as well as streamlined syntheses of homocrotylation reagents.

  DOI：

  10.1021/jacs.5b08858

文献信息

• Copper-Catalyzed Amino Lactonization and Amino Oxygenation of Alkenes Using <i>O</i>-Benzoylhydroxylamines
  作者：Brett N. Hemric、Kun Shen、Qiu Wang

  DOI：10.1021/jacs.6b02840

  日期：2016.5.11

  A copper-catalyzed amino lactonization of unsaturated carboxylic acids has been achieved as well as the analogous intermolecular three-component amino oxygenation of olefins. The transformation features mild conditions and a remarkably broad substrate scope, offering a novel and efficient approach to construct a wide range of amino lactones as well as 1,2-amino alcohol derivatives. Mechanistic studies

  已经实现了铜催化的不饱和羧酸的氨基内酯化以及烯烃的类似分子间三组分氨基氧化。该转化具有温和的条件和非常广泛的底物范围，为构建各种氨基内酯和 1,2-氨基醇衍生物提供了一种新颖而有效的方法。机理研究表明，该反应是通过独特的 O-苯甲酰羟胺促进的烯烃亲电胺化进行的。
• [EN] TRIAZOLE AGONISTS OF THE APJ RECEPTOR<br/>[FR] TRIAZOLES AGONISTES DU RÉCEPTEUR APJ
  申请人：AMGEN INC

  公开号：WO2016187308A1

  公开（公告）日：2016-11-24

  Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the following structures where the definitions of the variables are provided herein.

  公式I和公式II的化合物，其药用盐，上述任何一种的立体异构体，或它们的混合物是APJ受体的激动剂，并可用于治疗心血管和其他疾病。公式I和公式II的化合物具有以下结构，其中变量的定义在此提供。
• [EN] TRIAZOLE FURAN COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR<br/>[FR] COMPOSÉS DE TRIAZOLE FURANE UTILISÉS EN TANT QU'AGONISTES DU RÉCEPTEUR APJ
  申请人：AMGEN INC

  公开号：WO2018097944A1

  公开（公告）日：2018-05-31

  Compounds of Formula (I) and Formula (II), pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and have use in treating cardiovascular and other conditions. Compounds of Formula (I) and Formula (II) have the following structures: (I); (II). Intermediates (V) are also claimed.

  式(I)和式(II)的化合物，其药用盐，任何上述化合物的立体异构体，或它们的混合物是APJ受体的激动剂，并且在治疗心血管和其他疾病方面有用。式(I)和式(II)的化合物具有以下结构：(I); (II)。中间体(V)也被要求。
• Combining the Petasis 3-Component Reaction with Multiple Modes of Cyclization: A Build/Couple/Pair Strategy for the Synthesis of Densely Functionalized Small Molecules
  作者：Thomas Flagstad、Mette R. Hansen、Sebastian T. Le Quement、Michael Givskov、Thomas E. Nielsen

  DOI：10.1021/co500091f

  日期：2015.1.12

  strategy for the synthesis of complex and densely functionalized small molecules is presented. The strategy relies on synthetically tractable building blocks (build), that is, diversely substituted hydrazides, α-hydroxy aldehydes, and boronic acids, which undergo Petasis 3-component reactions (couple) to afford densely functionalized anti-hydrazido alcohols. The resulting scaffolds can subsequently

  提出了一种构建/偶联/配对策略，用于合成复杂且功能密集的小分子。该策略依赖于合成易处理的构建基（构建体），即不同取代的酰肼，α-羟基醛和硼酸，它们经历Petasis 3组分反应（偶合）以提供高密度官能化的抗酰肼醇。产生的支架随后可以通过化学选择性环化反应（对），包括分子内Diels-Alder或Ru-亚烷基催化的闭环复分解反应，仅需3-4个步骤即可以良好的产率转化成结构多样的杂环。
• FURO- AND THIENO-PYRIDINE CARBOXAMIDE COMPOUNDS USEFUL AS PIM KINASE INHIBITORS
  申请人：Incyte Corporation

  公开号：US20150057265A1

  公开（公告）日：2015-02-26

  The present disclosure describes furo- and thieno-pyridine carboxamide compounds, as well as their compositions and methods of use. The compounds inhibit the activity of the Pim kinases, and are useful in the treatment of diseases related to the activity of Pim kinases including, e.g., cancer and other diseases.

  本公开描述了呋喃和噻吩吡啶羧酰胺化合物，以及它们的组合物和使用方法。这些化合物抑制Pim激酶的活性，并且在治疗与Pim激酶活性相关的疾病方面具有用处，例如癌症和其他疾病。