2-(2-oxo-2H-chromen-6-yl)acetonitrile | 142588-42-9

• 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: 2-(2-oxo-2H-chromen-6-yl)acetonitrile
• 英文别名: (2-oxo-2H-chromen-6-yl)-acetonitrile；6-cyanomethylcoumarin；2-(2-Oxochromen-6-yl)acetonitrile
• CAS: 142588-42-9
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: MDKDZFBQBATNGG-UHFFFAOYSA-N

物化性质

• 沸点：
  413.4±45.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-oxo-2H-chromen-6-yl)acetonitrile 以 盐酸 、 甲醇 、 乙酸乙酯 为溶剂， 生成 6-carbomethoxymethylcoumarin
  参考文献：
  名称：

  Substituted monocyclic aryl compounds exhibiting selective leukotriene

  摘要：

  具有选择性LTB.sub.4拮抗剂性质的单环芳基化合物，包括一个酰胺取代基、一个带有末端羧酸或其衍生物的取代基团和一个亲脂性取代基，以及使用这些单环芳基化合物的治疗组合物和治疗因LTB.sub.4活性引起的疾病的方法被揭示。

  公开号：

  US05232948A1
• 作为产物：
  描述：

  6-甲基香豆素 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 2-(2-oxo-2H-chromen-6-yl)acetonitrile
  参考文献：
  名称：

  A Novel Series of [2-[Methyl(2-phenethyl)amino]-2-oxoethyl]benzene-Containing Leukotriene B₄ Antagonists:  Initial Structure−Activity Relationships

  摘要：

  This report describes the synthesis of a new class of LTB(4) receptor antagonists containing [2-[methyl(2-phenethyl)amino]-2-oxoethyl]benzene as a key binding domain for interaction with high-affinity LTB(4) receptors. In addition to this binding domain, two other structural features, an acid function and a lipophilic group, are also required by these compounds for high binding affinity, Our studies indicate that maximal binding affinity in this series is controlled by the spatial relationship of these groups relative to one another, The structure-activity relationships are discussed, The most potent compound in this chemical series, (E)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (32), has an IC50 of 2 nM in a guinea pig spleen cell membrane assay, In the whale-cell human neutrophils binding assay, (Z)-5-[2-[methyl(2-phenethyl)amino]-2-oxoethyl]-2-(benzyloxy)cinnamic acid (30) was the most potent compound with an IC50 of 50 nM.

  DOI：

  10.1021/jm9506985

文献信息

• Palladium-Catalyzed Synthesis of Benzofurans and Coumarins from Phenols and Olefins
  作者：Upendra Sharma、Togati Naveen、Arun Maji、Srimanta Manna、Debabrata Maiti

  DOI：10.1002/anie.201305326

  日期：2013.11.25

  Triple CH functionalization: Palladium‐catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential CH functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms.

  三重CH官能化：描述了通过酚与未活化的烯烃反应，钯催化合成苯并呋喃和香豆素。该反应包括顺序的CH官能化，并显示出各种官能团相容性。初步的机理研究阐明了可能的机制。
• Development of Fluorogenic Substrates For Monoamine Oxidases (Mao-A and Mao-B)
  申请人：Chen Gong

  公开号：US20080194522A1

  公开（公告）日：2008-08-14

  The present invention relates to compounds useful for detecting the activity of monoamine oxidases, compounds useful for competitively inhibiting monoamine oxidases, for determining inhibitors of monoamine oxidases and compounds useful for treating monoamine oxidase-related nervous system pathologies, as well as pharmaceutical compositions and methods of manufacture thereof.

  本发明涉及用于检测单胺氧化酶活性的化合物，用于竞争性抑制单胺氧化酶的化合物，用于确定单胺氧化酶抑制剂和用于治疗与单胺氧化酶相关的神经系统病理的化合物，以及制药组合物和制造方法。
• [EN] DEVELOPMENT OF FLUOROGENIC SUBSTRATES FOR MONOAMINE OXIDASES (MAO-A AND MAO-B)<br/>[FR] MISE AU POINT DE SUBSTRATS FLUOROGENES DESTINES AUX MONOAMINE OXYDASES (MAO-A AND MAO-B)
  申请人：F NEW YORK THE TRUSTEES OF COL

  公开号：WO2006026368A3

  公开（公告）日：2006-08-31
• SUBSTITUTED MONOCYCLIC ARYL COMPOUNDS EXHIBITING SELECTIVE LEUKOTRIENE B 4? ANTAGONIST ACTIVITY
  申请人：RHONE-POULENC RORER INTERNATIONAL (HOLDINGS) INC.

  公开号：EP0538416A1

  公开（公告）日：1993-04-28
• EP0538416A4
  申请人：——

  公开号：EP0538416A4

  公开（公告）日：1994-05-18