4-甲酰基-3-甲氧基苯硼酸 | 815620-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲酰基-3-甲氧基苯硼酸
• 中文别名: 4-甲酰基-3-甲氧基苯基硼酸
• 英文名称: (4-formyl-3-methoxyphenyl)boronic acid
• CAS: 815620-00-9
• 化学式: C₈H₉BO₄
• mdl: MFCD10697427
• 分子量: 179.968
• InChiKey: LZVMUJGTTXMMTE-UHFFFAOYSA-N

物化性质

• 熔点：
  214-217 °C
• 沸点：
  400.8±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338,P304+P340,P405
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  1,3,6,8-四溴芘 、 4-甲酰基-3-甲氧基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以84 %的产率得到C₄₈H₃₄O₈
  参考文献：
  名称：

  铑催化脱氢环化构建超稳定非取代喹啉桥共价有机骨架

  摘要：

  报道了通过铑催化的 [4+2] 环化对动态亚胺桥进行无氧化剂锁定以构建超稳定的非取代喹啉连接的 COF。该方法具有高效性、通用性、结晶度和拓扑结构的保留。增强的平面内π共轭促进了由超氧阴离子自由基介导的光催化有机转化。

  DOI：

  10.1002/anie.202208833

文献信息

• Bulky <i>N</i> ‐Heterocyclic‐Carbene‐Coordinated Palladium Catalysts for 1,2‐Addition of Arylboron Compounds to Carbonyl Compounds
  作者：Yuta Okuda、Masahiro Nagaoka、Tetsuya Yamamoto

  DOI：10.1002/cctc.202001464

  日期：2020.12.16

  primary, secondary, and tertiary alcohols by the 1,2‐addition of arylboronic acids or boronates to carbonyl compounds, including unactivated ketones, using novel bulky yet flexible N‐heterocyclic carbene (NHC)‐coordinated 2,6‐di(pentan‐3‐yl)aniline (IPent)‐based cyclometallated palladium complexes (CYPs) as catalysts is reported. The PhS‐IPent‐CYP‐catalyzed reactions are efficient at low catalyst loadings

  使用新型但又灵活的N杂环卡宾（NHC）配位的2,6-di（据报道以戊烷-3-基）苯胺（IPent）为基的环金属化钯配合物（CYPs）。PhS-IPent-CYP催化的反应在低催化剂负载量（0.02-0.3 mol％Pd）下有效，而1,2-加成的出色催化活性归因于NHC配体的空间体积。这些反应可产生各种功能化的苄醇，这些化合物很难通过经典方案使用高活性有机镁或锂试剂进行合成。
• [EN] BRD9 BIFUNCTIONAL DEGRADERS AND THEIR METHODS OF USE<br/>[FR] AGENTS DE DÉGRADATION BIFONCTIONNELS BRD9 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：NOVARTIS AG

  公开号：WO2021055295A1

  公开（公告）日：2021-03-25

  The disclosure provides BRD9 bifunctional compounds of Formula (A) or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, or tautomer thereof, to their preparation, to pharmaceutical compositions comprising them, and to their use in the treatment of diseases and disorders mediated by a bromodomain-containing protein, such as bromodoma in-containing protein 9 (BRD9)

  该披露提供了公式（A）的BRD9双功能化合物或其药用可接受的盐、水合物、溶剂合物、前药、立体异构体或互变异构体，以及它们的制备方法、包含它们的药物组合物，以及它们在治疗由含溴结构域蛋白介导的疾病和紊乱中的应用，例如含溴结构域蛋白9（BRD9）。
• Enhanced protonation ability of covalent organic frameworks <i>via N</i>,<i>O</i>-bidentate chelation for photocatalytic H₂ evolution
  作者：Xing Li、Huaji Pang、Yanqiu Zhu、Yonggang Xiang、Jianxiang Hu、Dekang Huang

  DOI：10.1039/d3cc05558b

  日期：——

  Inspired by the bidentate coordination chemistry of metal ions, we incorporated hydroxyl (OH) and methoxy (OMe) groups into the skeleton of imine-linked COFs to improve their protonation ability via intramolecular hydrogen bonds (O–H⋯NC). In comparison with the pristine COFs possessing monodentate nitrogen coordination sites, OH and OMe functionalized COFs with (N,O)-bidentate chelating sites exhibited

  受金属离子双齿配位化学的启发，我们将羟基（OH）和甲氧基（OMe）基团引入亚胺连接的COF的骨架中，通过分子内氢键（O–H⋯N）提高其质子化能力 C）。与具有单齿氮配位位点的原始COF相比，具有( N , O )-二齿螯合位点的OH和OMe功能化COF表现出高达13.8倍的光催化析氢速率(HER)。
• Palladium-Catalyzed Hydroxymethylation of Aryl- and Heteroarylboronic Acids using Aqueous Formaldehyde
  作者：Tetsuya Yamamoto、Azamat Zhumagazin、Takuma Furusawa、Ryoji Tanaka、Tetsu Yamakawa、Yohei Oe、Tetsuo Ohta

  DOI：10.1002/adsc.201400845

  日期：2014.11.24

  AbstractCyclometallated NHC palladium complexes prepared from palladium(II) acetate [Pd(OAc)2] and unsymmetrical 1,3‐diarylimidazolinium salts catalyzed the hydroxymethylation of (hetero)arylboronic acids using an excess amount of formalin to afford (hetero)arylmethanols in good to satisfactory yields.magnified image
• Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts
  作者：Andiliy Lai、Mehmet Kahraman、Steven Govek、Johnny Nagasawa、Celine Bonnefous、Jackie Julien、Karensa Douglas、John Sensintaffar、Nhin Lu、Kyoung-jin Lee、Anna Aparicio、Josh Kaufman、Jing Qian、Gang Shao、Rene Prudente、Michael J. Moon、James D. Joseph、Beatrice Darimont、Daniel Brigham、Kate Grillot、Richard Heyman、Peter J. Rix、Jeffrey H. Hager、Nicholas D. Smith

  DOI：10.1021/acs.jmedchem.5b00054

  日期：2015.6.25

  Approximately 80% of breast cancers are estrogen receptor alpha, (ER-a) positive, and although women typically initially respond, well to antihormonal therapies such as tamoxifen and aromatase inhibitors, resistance often emerges. Although a variety of resistance mechanism may be at play in this state, there is evidence that in many cases the ER still plays a central role, including mutations in the ER leading to constitutively active receptor. Fulvestrant is a steroid-based, selective estrogen receptor degrader., (SEED) That both antagonizes and degrades ER-alpha and is active in patients who have progressed on antihormonal agents. However, fulvestrant suffers from poor pharmaceutical properties and must be administered by intramuscular injections that limit the total amount of drug that can be administered and hence lead to the potential for incomplete receptor blockade. We describe the identification and characterization of a series of small-molecule, orally bioavailable SERDs, which are potent antagonists and degraders of ER-alpha and in which the ER-alpha degrading properties were prospectively optimized. The lead compound 111 (GDC-0810 or ARN-810) demonstrates robust activity in models of tamoxifen-sensitive and tamoxifen-resistant breast cancer, and is currently in clinical trials in women with locally advanced or metastatic estrogen receptor-positive breast cancer.