1-戊烯基硼酸 | 104376-24-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 1-戊烯基硼酸
• 英文名称: (E)-1-pentenylboronic acid
• 英文别名: (E)-pent-1-en-1-ylboronic acid；trans-1-penten-1-ylboronic acid；(E)-pent-1-enylboronic acid；1-pentenylboronic acid；(E)-1-penten-1-ylboronic acid；1-penten-1-ylboronic acid；(E)-pentenylboronic acid；Pent-1-en-1-ylboronic acid；[(E)-pent-1-enyl]boronic acid
• CAS: 104376-24-1；59239-44-0
• 化学式: C₅H₁₁BO₂
• 分子量: 113.952
• InChiKey: SYKWJOZHNDPWIM-SNAWJCMRSA-N

物化性质

• 熔点：
  100-105 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  1-戊烯基硼酸 在 吡啶 、 四(三苯基膦)钯 、 二苯基二硒醚 、 potassium carbonate 、 N-氟代双苯磺酰胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 2-propyl-1-tosyl-1H-indole
  参考文献：
  名称：

  硒催化的烯烃的氧化C（sp 2）–H胺化反应在（Aza-）吲哚类化合物的合成中得到了很好的体现

  摘要：

  报道了一种使用N-氟苯磺酰亚胺作为末端氧化剂直接，分子内胺化C（sp 2）-H键的新的硒催化方案。该方法能够容易地形成分别衍生自容易获得的邻乙烯基苯胺和乙烯基化氨基吡啶的多种多样的功能化的吲哚和氮杂吲哚。该方法利用硒亲电试剂的显着的亲碳性来催化烯烃的活化，并导致高产率且具有出色的官能团耐受性的C（sp 2）–N键形成。

  DOI：

  10.1021/acs.orglett.5b01156
• 作为产物：
  描述：

  (E)-pent-1-en-1-yl-1,3,2-benzodioxaborole 在 水 作用下， 反应 1.0h， 以87%的产率得到1-戊烯基硼酸
  参考文献：
  名称：

  2-Pyrones possessing antimicrobial and cytotoxic activities

  摘要：

  The 2-pyrone sub-unit is found in a number of natural products possessing broad spectrum biological activity. Such compounds are validated as being capable of binding to specific protein domains and able to exert a remarkable range of biological effects. In an effort to identify synthetic 2-pyrones with interesting biological effects, herein we report the synthesis and biological evaluation of 4-substituted-6-methyl-2-pyrones. Synthetic routes to 4-alkyl/alkenyl/aryl/alkynyl-6-methyl-2-pyrones have been developed utilising Sonogashira, Suzuki and Negishi cross-coupling starting from readily available 4-bromo-6-methyl-2-pyrone. Specific conditions for each organometallic protocol were required for successful cross-coupling. In particular, a triethylamine/acetonitrile-base/solvent mixture was crucial to Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone, whereas thallium carbonate was a mandatory base for the Suzuki cross-coupling of trialkylboranes. The 2-pyrones demonstrate potent inhibitory activity against Bacillus subtilis, Escherichia coli, Staphylococcus aureus, Schizosaccharomyces pombe and Botrytis cinerea. The growth inhibitory activities of selected 2-pyrones were determined in A2780 human ovarian carcinoma and K562 human chronic myelogenous leukaemia cell lines using an in vitro cell culture system (MTT assay). These studies demonstrate that 4-phenylethynyl-, 4-tetrahydropyranylpropargyl ether- and 4-ethynyl-6-methyl-2-pyrones have excellent potential as a new class of anticancer agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.051

文献信息

• Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones
  作者：Amy Boylan、Thien S. Nguyen、Brian J. Lundy、Jian-Yuan Li、Ravikrishna Vallakati、Sasha Sundstrom、Jeremy A. May

  DOI：10.3390/molecules26061615

  日期：——

  Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the

  影响烯基硼酸与杂芳基连接的烯酮共轭加成反应速率的两个关键因素：感应吸电子杂原子与成键位点的接近度以及可用杂原子孤对对稳定产生的正电荷的共振贡献在烯酮β-位。对于前者，杂原子距离烯酮β-碳越近，反应越快。对于后者，苄基阳离子电荷的共振稳定性更强，可加速反应。因此，反应速率通过感应吸电子元件的更接近而增加，但如果涉及共振效应，则观察到具有给电子能力的速率增加。提出了异构底物这些趋势的证据，并且这些见解的应用允许反应条件改善与以前有问题的底物的反应性。
• [EN] HETEROAROMATIC AND HETEROBICYCLIC AROMATIC DERIVATIVES FOR THE TREATMENT OF FERROPTOSIS-RELATED DISORDERS<br/>[FR] DÉRIVÉS AROMATIQUES HÉTÉROBICYCLIQUES ET HÉTÉROAROMATIQUES POUR LE TRAITEMENT DE TROUBLES LIÉS À LA FERROPTOSE
  申请人：COLLABORATIVE MEDICINAL DEV LLC

  公开号：WO2020185738A1

  公开（公告）日：2020-09-17

  The present application discloses heteroaromatic and heterobicyclic aromatic derivative compounds and compositions, and methods for treating ferroptosis-related disorders and diseases in patients using the compounds and compositions as disclosed herein.

  本申请公开了杂芳和杂双环芳香衍生物化合物和组合物，以及利用所公开的化合物和组合物治疗患者的铁死亡相关疾病和疾病的方法。
• Macrocyclic MCL-1 inhibitors and methods of use
  申请人：AbbVie Inc.

  公开号：US20190055264A1

  公开（公告）日：2019-02-21

  The present disclosure provides for compounds of Formula (I) wherein A 2 , A 3 , A 4 , A 6 , A 7 , A 8 , A 15 , R A , R 5 , R 9 , R 10A , R 10B , R 11 , R 12 , R 13 , R 14 , R 16 , W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents for the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

  本公开提供了Formula (I)的化合物，其中A2、A3、A4、A6、A7、A8、A15、RA、R5、R9、R10A、R10B、R11、R12、R13、R14、R16、W、X和Y具有规范中定义的任何值，以及其药学上可接受的盐，可用作治疗疾病和病况的药物，包括癌症。还提供了包含Formula (I)化合物的药物组合物。
• Pincer-type bis(carbene)-derived complexes of nickel(II): Synthesis, structure, and catalytic activity
  作者：Kiyofumi Inamoto、Jun-ichi Kuroda、Eunsang Kwon、Kou Hiroya、Takayuki Doi

  DOI：10.1016/j.jorganchem.2008.11.003

  日期：2009.2

  Air- and moisture-stable NHC (N-heterocyclic carbene)-derived CNC-type pincer complexes of nickel(II) 4a–d were successfully synthesized, and their structures were fully characterized using X-ray crystallography and analytical and spectroscopic methods. These complexes exhibit a high catalytic activity for the Suzuki–Miyaura coupling reaction of aryl bromides and chlorides with aryl- and alkenylboronic

  成功合成了由空气和水分稳定的NHC（N-杂环卡宾）衍生的CNC型镍（II）4a - d络合物，并使用X射线晶体学，分析和光谱方法对它们的结构进行了充分表征。这些络合物对芳烃溴化物和氯化物与芳基和链烯基硼酸的Suzuki-Miyaura偶联反应具有很高的催化活性，通常可以高收率提供一系列联苯和对苯二甲酸酯。
• Study of the Structure–Activity Relationship in a Heterogeneous Copper–Palladium Catalysed Suzuki–Miyaura Coupling
  作者：Anna Fodor、Ágnes Magyar、Dóra Barczikai、Laurence Pirault-Roy、Zoltán Hell

  DOI：10.1007/s10562-015-1490-y

  日期：2015.3

  applied in the Suzuki–Miyaura reaction. The reaction took place with a variety of substituted boronic acids as well as with a collection of iodo- and bromobenzene derivatives. In some cases steric effects had influence on the reaction, ortho-substituted iodo- or bromobenzenes gave lower yield independently from the substituent. But most m- and p-substituted iodo- and bromobenzenes showed good to excellent

  通过两步湿法浸渍制备的 4 Å 分子筛负载的铜钯双金属催化剂成功应用于 Suzuki-Miyaura 反应。该反应与多种取代的硼酸以及一系列碘苯和溴苯衍生物发生。在某些情况下，空间效应对反应有影响，邻位取代的碘苯或溴苯的产率较低，与取代基无关。但大多数间位和对位取代的碘苯和溴苯表现出良好至极好的活性。通过两种甚至三种途径获得了几种联苯：硼酸或相应的碘苯或溴苯被官能化。 图形摘要