2-甲基苯并呋喃-3-甲醛 | 55581-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2-甲基苯并呋喃-3-甲醛
• 英文名称: 2-methylbenzofuran-3-carbaldehyde
• 英文别名: 2-methyl-1-benzofuran-3-carbaldehyde
• CAS: 55581-61-8
• 化学式: C₁₀H₈O₂
• mdl: MFCD00625450
• 分子量: 160.172
• InChiKey: MSCYILGZMAMAQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-甲基苯并呋喃-3-甲醛 生成 2,3-二甲基苯呋喃
  参考文献：
  名称：

  Bisagni et al., Journal of the Chemical Society, 1955, p. 3688,3692

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基苯并呋喃 在 sodium hydroxide 、 三氯氧磷 作用下， 反应 8.25h， 生成 2-甲基苯并呋喃-3-甲醛
  参考文献：
  名称：

  Pearson, James R.; Porter, Quentin N., Australian Journal of Chemistry, 1991, vol. 44, # 8, p. 1085 - 1095

  摘要：

  DOI：

文献信息

• Cyclopenta[<i>b</i>]annulation of Heteroarenes by Organocatalytic γ′[C(sp³)−H] Functionalization of Ynones
  作者：Moluguri Raghu、Jagdeep Grover、S. S. V. Ramasastry

  DOI：10.1002/chem.201604562

  日期：2016.12.19

  to the designed ynones triggers γ′[C(sp3)−H] functionalization, leading to the formation of heteroaryl‐based ortho‐quinodimethane (oQDM) intermediates that undergo carbocyclization to provide cyclopentannulated heteroarenes in good yields and excellent stereoselectivities. Deuterium‐labeling experiments substantiated the proposed reaction mechanism as well as the speculated epimerization.

  对于环戊二烯并[一种新方法b通过金属和无定向基团的γ'[C（SP杂芳烃的]环3）-H]官能化和ynones的分子内加氢烷基化得到了发展。在史无前例的事件中，将有机膦亲核加成到设计的炔酮上会触发γ'[C（sp 3）-H]功能化，导致形成杂芳基邻喹啉二甲烷（oQDM）中间体，该中间体经过碳环化作用以提供环戊环杂芳烃具有良好的收率和出色的立体选择性。氘标记实验证实了拟议的反应机理以及推测的差向异构。
• Palladium-catalysed annulative allylic alkylation for the synthesis of benzannulated heteroarenes
  作者：Sonu Yadav、S. S. V. Ramasastry

  DOI：10.1039/d0cc06695h

  日期：——

  A conceptually novel intramolecular allylic alkylation strategy is developed for the synthesis of carbazoles and dibenzothiophenes. In an unusual event, palladium catalyses the formation of π-allylpalladium complexes of the respective (2-methylindol-3-yl)allyl acetates and subsequently facilitates the benzannulation process.

  为合成咔唑和二苯并噻吩开发了一种概念上新颖的分子内烯丙基烷基化策略。在不寻常的情况下，钯催化相应的（2-甲基吲哚-3-基）烯丙基乙酸酯的π-烯丙基钯络合物的形成，并随后促进苯甲环化过程。
• Synthesis of Chiral Polycyclic Tetrahydrocarbazoles by Enantioselective Aminocatalytic Double Activation of 2-Hydroxycinnamaldehydes with Dienals
  作者：Yong-Chao Ming、Xue-Jiao Lv、Ming Liu、Yan-Kai Liu

  DOI：10.1021/acs.orglett.1c02309

  日期：2021.8.20

  An efficient aminocatalytic enantioselective double-activation strategy has been developed that combines several different aminocatalytic modes in a cascade process, such as iminium ion, vinylogous iminium ion, trienamine, and dienamine activations. By using this strategy, 2-hydroxycinnamaldehydes worked well with various dienals via [4 + 2] cycloaddition and the oxa-Michael reaction-initiated cascade

  已经开发了一种有效的氨基催化对映选择性双活化策略，它在级联过程中结合了几种不同的氨基催化模式，例如亚胺离子、乙烯基亚胺离子、三烯胺和二烯胺活化。通过使用这种策略，2-羟基肉桂醛分别通过 [4 + 2] 环加成和 oxa-Michael 反应引发的级联与各种二烯很好地配合，从而产生具有优异非对映选择性和对映选择性的手性多环四氢咔唑和色满衍生物。
• Organocatalytic asymmetric synthesis of dihydrocarbazoles via a formal [4+2] cycloaddition of in situ generated o-quinodimethanes with enals
  作者：Bo-Qi Gu、Hao Zhang、Ruo-Heng Su、Wei-Ping Deng

  DOI：10.1016/j.tet.2016.08.077

  日期：2016.10

  An organocatalytic asymmetric [4+2] eliminative cycloaddition reaction of 2-methyl-indolyl methylenemalononitriles with α,β-unsaturated aldehydes via in situ generated indole-ortho-quinodimethane intermediates has been developed. This approach provides straightforward access to 2,9-dihydro-1H-carbazole-3-carbaldehydes, as well as its analogous dihydrodibenzofuran and dihydrodibenzothiophene in good

  通过原位生成的吲哚-邻-邻-喹二甲烷中间体，开发了2-甲基-吲哚基亚甲基丙二腈与α，β-不饱和醛的有机催化不对称[4 + 2]消除环加成反应。这种方法可直接获得2,9-二氢-1 H-咔唑-3-甲醛及其类似的二氢二苯并呋喃和二氢二苯并噻吩，且收率高且对映选择性高。
• [EN] NOVEL COMPOUNDS AND THEIR USE<br/>[FR] NOUVEAUX COMPOSÉS ET LEUR UTILISATION
  申请人：DEBIOPHARM INT SA

  公开号：WO2021123372A1

  公开（公告）日：2021-06-24

  The present invention provides compounds of the general formula (I) or a pharmaceutically acceptable prodrugs, salts and/or solvates thereof, wherein LHS is selected from the group consisting of LHSa and LHSb And wherein, the asterisk (*) marks the point of attachment; These compounds exhibit antibacterial activity against Gram-negative and Gram-positive bacteria, especially S. aureus, E. coli, K. pneumoniae and A. baumannii. Pharmaceutical compositions containing these compounds, therapeutic uses thereof and methods for manufacturing the same are also provided.

  本发明提供了一般式（I）的化合物或其药用可接受的前药、盐和/或溶剂化合物，其中LHS选自LHSa和LHSb组成的组，星号（*）标记附着点；这些化合物对革兰氏阴性和革兰氏阳性细菌，特别是金黄色葡萄球菌、大肠杆菌、肺炎克雷伯菌和鲍曼不动杆菌表现出抗菌活性。还提供了含有这些化合物的药物组合物、其治疗用途和制备方法。