2-(benzofuran-2-yl)benzaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(benzofuran-2-yl)benzaldehyde
• 英文别名: 2-Benzofuranylphenyl-methanone；2-(1-benzofuran-2-yl)benzaldehyde
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: JODPRUACXRHHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzofuran-2-yl)benzaldehyde 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(2-(benzofuran-2-yl)phenyl)ethan-1-one
  参考文献：
  名称：

  o-Quinone Methides via Oxone-Mediated Benzofuran Oxidative Dearomatization and Their Intramolecular Cycloaddition with Carbonyl Groups: An Expeditious Construction of the Central Tetracyclic Core of Integrastatins, Epicoccolide A, and Epicocconigrone A

  摘要：

  The intramolecular cycloaddition of o-quinone methides (o-QMs) with a carbonyl group has been envisaged and executed successfully in the context of constructing the complex and rare [6,6,6,6]-tetracyclic core found in the integrastatins, epicoccolide A, and epicocconigrone A. These transient o-QMs were generated easily from the oxidative dearomatization of the corresponding C2-(aryl)benzofuran by employing Oxone in acetone-water at rt. The subsequent cydoaddition with the carbonyl (or conjugated olefin) present on the C2-aryl group was spontaneous.

  DOI：

  10.1021/acs.orglett.5b03707
• 作为产物：
  描述：

  2,3-苯并呋喃 、 邻溴苯甲醛 在 N-甲基-D-天冬氨酸 、 potassium acetate 、 palladium diacetate 作用下， 反应 15.0h， 以67%的产率得到2-(benzofuran-2-yl)benzaldehyde
  参考文献：
  名称：

  o-Quinone Methides via Oxone-Mediated Benzofuran Oxidative Dearomatization and Their Intramolecular Cycloaddition with Carbonyl Groups: An Expeditious Construction of the Central Tetracyclic Core of Integrastatins, Epicoccolide A, and Epicocconigrone A

  摘要：

  The intramolecular cycloaddition of o-quinone methides (o-QMs) with a carbonyl group has been envisaged and executed successfully in the context of constructing the complex and rare [6,6,6,6]-tetracyclic core found in the integrastatins, epicoccolide A, and epicocconigrone A. These transient o-QMs were generated easily from the oxidative dearomatization of the corresponding C2-(aryl)benzofuran by employing Oxone in acetone-water at rt. The subsequent cydoaddition with the carbonyl (or conjugated olefin) present on the C2-aryl group was spontaneous.

  DOI：

  10.1021/acs.orglett.5b03707

文献信息

• Benzylamine derivatives which are useful in treating psychiatric
  申请人：Akzo Nobel, N.V.

  公开号：US06080773A1

  公开（公告）日：2000-06-27

  The present invention relates to certain novel benzylamine derivatives, to processes for their preparation, to pharmaceutical formulations containing them and to their use in medical therapy, particularly in the treatment of depression.

  本发明涉及某些新颖的苯甲基胺衍生物，其制备方法，含有它们的药物制剂及其在医疗治疗中的用途，特别是在抑郁症治疗中的用途。
• Cationic Cascade for Building Complex Polycyclic Molecules from Simple Precursors: Diastereoselective Installation of Three Contiguous Stereogenic Centers in a One-Pot Process
  作者：Georgios Alachouzos、Alison J. Frontier

  DOI：10.1021/jacs.8b11713

  日期：2019.1.9

  Friedel-Crafts allylation. The entire sequence forms three carbon-carbon bonds and a carbon-halogen bond, generating halocyclopentene adducts in one pot from simple precursors. The process occurs with excellent diastereocontrol, providing highly functionalized polycycles containing three tertiary or quaternary stereogenic centers in a linear array. It is even possible to install three contiguous all-carbon quaternary

  描述了合成多环小分子的权宜之计。该方法首先使用炔基卤代-Prins 协议将两个非手性构件（烯炔和醛或酮）连接在一起。然后，在同一反应容器中，酸性条件引发阳离子级联反应，包括立体有择的卤代-纳扎罗夫电环化和非对映选择性的弗里德尔-克拉夫茨烯丙基化。整个序列形成三个碳 - 碳键和一个碳 - 卤素键，从简单的前体在一锅中生成卤代环戊烯加合物。该过程以出色的非对映控制发生，提供包含线性阵列中的三个三级或四级立体中心的高度功能化的多环。甚至可以使用这种方法安装三个连续的全碳四元中心。
• General Method for Functionalized Polyaryl Synthesis via Aryne Intermediates
  作者：Thanh Truong、Milad Mesgar、Ky Khac Anh Le、Olafs Daugulis

  DOI：10.1021/ja504886x

  日期：2014.6.18

  complements transition-metal-catalyzed direct arylation and allows access to structures that are not easily accessible via other direct arylation methods. The reactions are highly functional-group tolerant, with alkene, ether, dimethylamino, trifluoromethyl, ester, cyano, halide, hydroxyl, and silyl functionalities compatible with reaction conditions.

  描述了通过芳基卤和芳基三氟甲磺酸酯对芳烃和杂环进行碱促进的芳基化的方法。此外，还开发了对苯炔与去质子化芳烃或杂环反应中产生的ArLi中间体进行原位亲电捕获，从而可以快速、轻松地获得各种高度官能化的多芳基化合物。碱基促进的芳基化方法补充了过渡金属催化的直接芳基化，并允许获得通过其他直接芳基化方法不易获得的结构。该反应具有高度官能团耐受性，烯烃、醚、二甲氨基、三氟甲基、酯、氰基、卤化物、羟基和甲硅烷基官能团与反应条件兼容。
• A new synthetic approach to 6-unsubstituted phenanthridine and phenanthridine-like compounds under mild and metal-free conditions
  作者：Jumreang Tummatorn、Suppachai Krajangsri、Krissada Norseeda、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1039/c4ob00797b

  日期：——

  A new and mild synthetic approach for the synthesis of 6-unsubstituted phenanthridine and phenanthridine-like compounds under metal-free conditions at room temperature has been developed. The strategy involved a tandem azide rearrangement/intramolecular annulation and oxidation reactions of biarylmethyl azide precursors to obtain the desired products in up to 99% yields with high regioselectivity.

  在室温下于无金属条件下，开发了一种用于合成6-未取代菲啶及其类似化合物的新型温和合成方法。该策略涉及二芳基甲基叠氮前体的串联叠氮重排/分子内环化及氧化反应，以高达99%的产率和高区域选择性获得目标产物。
• Regioselectivity‐Switchable Intramolecular Hydroarylation of Ynone
  作者：Feng Wu、Shiwei Lu、Shifa Zhu

  DOI：10.1002/adsc.202001152

  日期：2020.12.22

  catalytic approach to the regioselective intramolecular hydroarylation of ynone has been developed. When ZnI2 was used as catalyst, the umpolung α‐arylation of ynone was realized via an addition‐elimination process of iodine ion to generate the ortho‐phenanthrenequinone methide (o‐PQM), which could be trapped by styrene to form benzo[f,h]chromenes through hetero‐Diels‐Alder reaction. While IPrAuCl/AgSbF6

  已开发出可转换的催化方法用于炔酮的区域选择性分子内氢芳基化。当ZnI 2用作催化剂时，通过碘离子加成消除过程生成邻菲菲醌（o ‐PQM），从而使炔酮的α-芳基化形成芳基，芳烃可被苯乙烯捕获从而形成苯并[ f]。中，h ]通过色烯杂-Diels-Alder反应。尽管应用了IPrAuCl / AgSbF 6，但发生了乙炔基的β芳基化反应，以中等至极好的收率得到了苯并环庚烯5一。