6,8-dichloro-2H-chromen-2-one | 20300-61-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,8-dichloro-2H-chromen-2-one
• 英文别名: 6,8-dichlorocoumarin；6,8-dichlorochromen-2-one
• CAS: 20300-61-2
• 化学式: C₉H₄Cl₂O₂
• 分子量: 215.036
• InChiKey: VXNXVBSMMLEIIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  6,8-dichloro-2H-chromen-2-one 在 盐酸 、 immobilized Pseudomonas cepacia lipase 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 ethyl (3R)-3-amino-3-(3,5-dichloro-2-hydroxyphenyl)propanoate
  参考文献：
  名称：

  R-Isomers of Arg-Gly-Asp (RGD) mimics as potent αvβ3 inhibitors

  摘要：

  The integrin alpha(v)beta(3), vitronectin receptor, is expressed in a number of cell types and has been shown to mediate adhesion of osteoclasts to bone matrix, vascular smooth muscle cell migration, and angiogenesis. We recently disclosed the discovery of a tripeptide Arg-Gly-Asp (RGD) mimic, which has been shown to be a potent inhibitor of the integrin alpha(v)beta(3) and has excellent anti-angiogenic properties including its suppression of tumor growth in animal models. In other investigations involving RGD mimics, only compounds containing the S-isomers of the beta-amino acids have been shown to be potent. We were surprised to find the potencies of analogs containing enantiomerically pure S-isomers of beta-amino acids which were only marginally better than the corresponding racemic mixtures. We therefore synthesized RGD mimics containing R-isomers of beta-amino acids and found them to be relatively potent inhibitors of alpha(v)beta(3). One of the compounds was examined in tumor models in mice and has been shown to significantly reduce the rate of growth and the size of tumors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.034
• 作为产物：
  描述：

  (E)-ethyl 3-(3,5-dichloro-2-hydroxyphenyl)acrylate 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到6,8-dichloro-2H-chromen-2-one
  参考文献：
  名称：

  香豆素类化合物的合成方法

  摘要：

  本发明公开了香豆素类化合物的一种合成方法，其结构式如下：其中，R1选自‑H、‑CH3、‑OCH3、‑F、‑Cl、‑Br、‑OH、‑NO2、N(CH2CH3)2的一种或几种，R2选自‑H、‑CH3或CH2CH3的一种。本发明直接利用2‑羟基肉桂酸酯类化合物为原料，在可见光催化的作用下，一步合成得到了香豆素类化合物。本发明的香豆素类化合物的合成方法，与现有合成方法相比，具有方法简单，条件温和，产率高的特点，反应在常温下进行，利用可见光作为反应能量来源，绿色无公害。

  公开号：

  CN106674175B

文献信息

• &agr;&ngr;&bgr;3 integrin antagonists in combination with chemotherapeutic agents
  申请人：——

  公开号：US06372719B1

  公开（公告）日：2002-04-16

  The present invention is directed to compounds of the formula and pharmaceutically acceptable salts and isomers thereof administered in combination with chemotherapeutic agents.

  本发明涉及以下结构的化合物及其药用盐和异构体，与化疗药物一起给药。
• Heterocyclic glycyl &bgr;-alanine derivatives
  申请人：G. D. Searle & Co.

  公开号：US06689754B1

  公开（公告）日：2004-02-10

  The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salts thereof, pharmaceutical compositions containing such compounds and methods of treating conditions mediated by the &agr;v&bgr;3 integrin.

  本发明涉及一类由化学式I表示的化合物，或其药学上可接受的盐，包含这类化合物的药物组合物以及治疗由αvβ3整合素介导的疾病的方法。
• Visible-Light-Induced Regioselective Alkylation of Coumarins via Decarboxylative Coupling with <i>N</i>-Hydroxyphthalimide Esters
  作者：Can Jin、Zhiyang Yan、Bin Sun、Jin Yang

  DOI：10.1021/acs.orglett.9b00327

  日期：2019.4.5

  An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate

  通过使用烷基N-羟基邻苯二甲酰亚胺酯作为烷基化试剂，开发了一种有效的香豆素的光催化脱羧3-位烷基化反应。事实证明，这种脱羧方法可耐受多种衍生自脂族羧酸（伯，仲和叔）的NHP酯，可提供中等收率至优异收率的广泛范围的3-烷基化香豆素衍生物。该协议因其条件温和，易于获得的起始原料，操作简便和宽泛的官能团耐受性而得到强调。
• Diacylation of coumarins by silver-catalyzed decarboxylative cross-coupling
  作者：Hua Wang、Shi-Liu Zhou、Li-Na Guo、Xin-Hua Duan

  DOI：10.1016/j.tet.2014.12.029

  日期：2015.1

  A mild silver-catalyzed decarboxylative acylation of coumarins has been developed by using α-oxocarboxylic acids as acyl sources. This protocol provides an efficient and straightforward access to aroyl substituted coumarins in moderate to excellent yields with good selectivities. Furthermore, the reaction conditions were also applicable to quinolinones and naphthoquinones, affording the corresponding

  通过使用α-氧代羧酸作为酰基源，已开发出温和的银催化香豆素的脱羧酰化反应。该方案以中等至极好的收率和良好的选择性，提供了直接，有效地获得芳酰基取代的香豆素的途径。此外，反应条件也适用于喹啉酮和萘醌，得到相应的酰化杂环化合物。
• Meta-azacyclic amino benzoic acid compounds and derivatives thereof
  申请人：G. D. Searle & Co.

  公开号：US06013651A1

  公开（公告）日：2000-01-11

  The present invention is directed to compounds of the formula ##STR1## and pharmaceutically acceptable salts and isomers thereof.

  本发明涉及公式##STR1##的化合物及其药用可接受的盐和异构体。