4-(but-3-en-1-yloxy)-2H-chromen-2-one | 73476-09-2

• 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: 4-(but-3-en-1-yloxy)-2H-chromen-2-one
• 英文别名: 4-But-3-enyloxy-1-benzopyran-2-one；4-but-3-enoxychromen-2-one
• CAS: 73476-09-2
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: PVICAYRKAKWMHS-UHFFFAOYSA-N

物化性质

• 沸点：
  376.6±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(but-3-en-1-yloxy)-2H-chromen-2-one 在 2,4,6-三甲基吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 28.0h， 生成 4-(4-octylcarboxy-(3-hydroxybutyloxy))coumarine
  参考文献：
  名称：

  Enzyme Activity Fingerprinting with Substrate Cocktails

  摘要：

  In the postgenomic era, emphasis is shifting from protein identification to protein functional analysis. Enzyme function can be characterized by measuring activity across series of substrates, which generates an activity profile or fingerprint. Activity fingerprinting is particularly useful to differentiate closely related enzymes. Previously reported fingerprinting methods use series of parallel measurements, which are complex and difficult to reproduce. Here we report a new method for fingerprinting enzyme activities based on using mixtures of substrates, or substrate cocktails, in a single reaction that is then analyzed by HPLC. The fingerprints produced are highly reproducible and allow functional differentiation and classification of closely related enzymes, as demonstrated for a series of lipases and esterases. The method is practical, general, and flexible in terms of reaction conditions and can be adapted to any reaction type.

  DOI：

  10.1021/ja0478330
• 作为产物：
  描述：

  4-溴-1-丁烯 、 4-羟基香豆素 在 四丁基碘化铵 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4-(but-3-en-1-yloxy)-2H-chromen-2-one
  参考文献：
  名称：

  可见光诱导的三氟甲磺酸钠和苯磺基硫代磺酸盐催化末端烯烃的硫代三氟甲基化

  摘要：

  开发了非常规的还原淬灭循环以实现可见光诱导的末端烯烃的硫代三氟甲基化。CF 3 SO 2 Na用作易于处理的CF 3自由基源，以中等至良好的产率提供所需的产物。这种转化具有温和的反应条件和广泛的底物范围。

  DOI：

  10.1039/c7cc03520a

文献信息

• Rhodium(III)-Catalyzed Aerobic Oxidative C–H Olefination of Unsaturated Acrylamides with Unactivated Olefins
  作者：Ravichandran Logeswaran、Masilamani Jeganmohan

  DOI：10.1021/acs.orglett.0c03981

  日期：2021.2.5

  unactivated alkenes via vinylic C–H activation has been developed. The present cross-coupling reaction was examined with a variety of differently functionalized acrylamides and unactivated olefins. In these reactions, highly valuable amide-functionalized butadienes were prepared in good to excellent yields. This protocol was also compatible with Weinreb amides. A possible reaction mechanism involving the chelation-assisted

  已经开发了铑（III）通过乙烯基C–H活化催化丙烯酰胺与未活化烯烃的好氧氧化交叉偶联。用多种不同官能化的丙烯酰胺和未活化的烯烃检查了目前的交叉偶联反应。在这些反应中，以高至优异的产率制备了非常有价值的酰胺官能化的丁二烯。该协议还与Weinreb酰胺兼容。提出了一种可能的反应机理，其中涉及通过羧酸盐辅助的去质子化途径进行螯合辅助的乙烯基C–H活化。
• Rhodium(III)-Catalyzed C–H Olefination of Aromatic/Vinyl Acids with Unactivated Olefins at Room Temperature
  作者：Subramanian Jambu、Masilamani Jeganmohan

  DOI：10.1021/acs.orglett.0c01636

  日期：2020.7.2

  A Rh(III)-catalyzed COOH-assisted C–H alkenylation of aromatic acids with unactivated alkenes at room temperature is described. Further, the highly challenging β-C–H olefination of acrylic acids with unactivated olefins was also demonstrated. In these reactions, ortho-alkenylated aromatic/vinylic acids were prepared in good to excellent yields. A possible reaction mechanism involving ortho C–H activation

  描述了在室温下用Rh（III）催化的COOH辅助芳香酸与未活化烯烃的CHH烯基化反应。此外，还证明了丙烯酸与未活化烯烃的极具挑战性的β-CHH烯化反应。在这些反应中，邻-alkenylated芳香族/乙烯基酸在良好制备以优异的产率。提出了一种可能的反应机理，涉及邻位C–H活化和五元rhodocycle的形成，并得到了氘标记研究和关键rhodocycle中间体的分离的支持。
• Ruthenium(II)-Catalyzed Redox-Neutral C–H Alkylation of Arylamides with Unactivated Olefins
  作者：Chikkabagilu Nagaraju Shambhavi、Masilamani Jeganmohan

  DOI：10.1021/acs.orglett.1c01575

  日期：2021.6.18

  A Ru(II)-catalyzed weak chelating group-aided ortho-C–H alkylation of arylamides with unactivated olefins in a redox-neutral fashion has been demonstrated. The present alkylation reaction was well-suited for various substituted arylamides and unactivated aliphatic alkenes. In this alkylation reaction, pivalic acid plays dual role in which it delivers the proton source in a protonation step and the

  已经证明了Ru(II) 催化的弱螯合基团辅助的芳基酰胺与未活化烯烃以氧化还原中性方式进行的邻位-C-H 烷基化反应。本烷基化反应非常适用于各种取代的芳基酰胺和未活化的脂肪族烯烃。在该烷基化反应中，新戊酸发挥双重作用，它在质子化步骤中提供质子源，相应的乙酸酯部分使芳基酰胺的邻位-C-H 键去质子化。
• Coumarins as iNOS inhibitors
  申请人：Jackson Sharon

  公开号：US20050054681A1

  公开（公告）日：2005-03-10

  The present invention relates to coumarins of the formula (I): that are useful as inhibitors of nitric oxide synthase. Pharmaceutical compositions and methods of using these compounds as inhibitors of nitric oxide synthase are described herein.

  本发明涉及一种具有以下结构的香豆素（I）：这些化合物可作为一氧化氮合酶的抑制剂。本文描述了这些化合物作为一氧化氮合酶抑制剂的药物组合物和使用方法。
• Indium(0)-Mediated C sp 3-S/O Cross-Coupling Approach Towards the Regioselective Alkylation of α-Enolic Esters/Dithioesters: A Mechanistic Insight
  作者：Sushobhan Chowdhury、Tanmoy Chanda、Ashutosh Gupta、Suvajit Koley、B. Janaki Ramulu、Raymond C. F. Jones、Maya Shankar Singh

  DOI：10.1002/ejoc.201301788

  日期：2014.5

  We have reported an indium(0)-mediated C sp 3–S/O cross-coupling approach that leads to the highly regioselective alkylation of α-enolic acetate/dithioacetate systems. This hetero cross-coupling reaction does not require additional co-catalyst or promoter, and the in situ generated organoindium species promotes the reaction by acting as the coupling partner of the α-enolic acetate/dithioacetate substrates

  我们已经报道了一种铟（0）介导的 C sp 3-S/O 交叉偶联方法，该方法导致 α-烯醇乙酸酯/二硫代乙酸酯系统的高度区域选择性烷基化。这种杂交叉偶联反应不需要额外的助催化剂或促进剂，原位生成的有机铟物质通过充当 α-烯醇乙酸酯/二硫代乙酸酯底物的偶联伙伴来促进反应。C-、S- 或 O-烷基化的出色选择性完全取决于 α-烯醇乙酸酯/二硫代乙酸酯体系的亲核行为。这些结果得到了底物和产物的相对电子能量的 DFT 计算以及相应转换的激活势垒的进一步支持。