2-(benzo[1,3]dioxol-5-ylethynyl)benzaldehyde | 1185881-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(benzo[1,3]dioxol-5-ylethynyl)benzaldehyde
• CAS: 1185881-86-0
• 化学式: C₁₆H₁₀O₃
• 分子量: 250.254
• InChiKey: ORRZTOKNVHHBHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(benzo[1,3]dioxol-5-ylethynyl)benzaldehyde 在 盐酸羟胺 、 potassium tert-butylate 、 碘 、 碳酸氢钠 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 34.0h， 生成 3-(4'-biphenyl)-4-iodoisoquinoline
  参考文献：
  名称：

  从N-（o-芳基乙炔基）苄基对甲苯磺酰胺与碘和碱轻松制备3-芳基-4-碘异喹啉

  摘要：

  在60℃下在NaHCO 3存在下用分子碘处理N-（邻-芳基乙炔基）苄基对甲苯磺酰胺，然后在室温下与t BuOK反应，以良好的收率得到3-芳基-4-碘异喹啉。将得到的3-芳基-4-碘异喹啉之一的4-碘-3-苯基异喹啉进一步平滑地转化为异喹啉衍生物。本方法是在无过渡金属的条件下由N-（邻-芳基乙炔基）苄基对甲苯磺酰胺制备3-芳基-4-碘异喹啉的一锅法。©2021爱思唯尔科学。版权所有。

  DOI：

  10.1016/j.tet.2021.131993
• 作为产物：
  描述：

  胡椒醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 16.47h， 生成 2-(benzo[1,3]dioxol-5-ylethynyl)benzaldehyde
  参考文献：
  名称：

  Functionalization of Csp3–H bond—Sc(OTf)3-catalyzed domino 1,5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum’s acids

  摘要：

  Under Sc(OTf)(3) catalysis, benzylidene Meldrum's acids bearing a tethered p-methoxyphenethyl group were observed to undergo a [1,5]-hydride shift/cyclization at room temperature, representing a mild Csp(3)-H bond functionalization. The resulting spiro Meldrum's acid intermediates then underwent intramolecular Friedel-Crafts acylation, completing the one-pot, domino reaction. The reported protocol generates the 6-6-5-6 tetracyclic core of tetrahydrobenzo[b]fluoren-11-ones. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.007

文献信息

• Silver‐Catalyzed Sequential Cascade Reaction of Isocyanides with 1‐(2‐Ethynyl‐phenyl)‐prop‐2‐yn‐1‐ol: Access to Benzo[ <i>b</i> ]fluorenes and Benzofuran‐Pyrroles
  作者：Jian‐Quan Liu、Xinyi Chen、Xuanyu Shen、Yihan Wang、Xiang‐Shan Wang、Xihe Bi

  DOI：10.1002/adsc.201801344

  日期：2019.4

  A silver‐catalyzed cycloaromatization of 1‐(2‐ethynyl‐phenyl)‐prop‐2‐yn‐1‐ol with isocyanides efficiently provides benzo[b]fluorene and benzofuran‐pyrrole derivatives through a modular cascade reaction that includes a nucleophilic attack on the diyne substrate. A C−C cross‐coupling/oxygen transportation/Diels‐Alder/hydrogen shift/isomerization cascade mechanistic pathway is proposed.

  银与异氰酸酯催化的1-（2-乙炔基-苯基）-丙-2-炔-1-醇的芳环芳香化反应可通过模块级联反应有效地提供苯并[ b ]芴和苯并呋喃-吡咯衍生物，包括对苯并的亲核攻击。二炔底物。提出了AC-C交叉偶联/氧迁移/ Diels-Alder /氢转移/异构化级联机制途径。
• Molecular iodine-mediated reaction of 2-(2-phenylethynyl)-Morita–Baylis–Hillman adducts: an easy route to naphthyl ketones and iodo-substituted isochromenes
  作者：Donala Janreddy、Veerababurao Kavala、Trimurtulu Kotipalli、R. R. Rajawinslin、Chun-Wei Kuo、Wen-Chang Huang、Ching-Fa Yao

  DOI：10.1039/c4ob00938j

  日期：——

  The iodine mediated reaction of 2-(2-phenylethynyl)-MBH gives corresponding naphthyl ketones and iodo-substituted isochromenes.

  碘介导的2-(2-苯乙炔基)-MBH的反应会生成相应的萘酮和碘取代的异色烯。
• Molecular Iodine-Mediated Cascade Reaction of 2-Alkynylbenzaldehyde and Indole: An Easy Access to Tetracyclic Indoloazulene Derivatives
  作者：Sachin D. Gawande、Veerababurao Kavala、Manoj R. Zanwar、Chun-Wei Kuo、Hsiu-Ni Huang、Chiu-Hui He、Ting-Shen Kuo、Ching-Fa Yao

  DOI：10.1002/adsc.201300421

  日期：2013.10.11

  AbstractThe synthesis of iodo‐substituted tetracyclic indole fused azulene derivatives was achieved from the reaction of 2‐(substituted phenylethynyl)benzaldehydes and different indoles in the presence of molecular iodine. The reaction involves the formation of a bisindole from the corresponding 2‐(substituted phenylethynyl)benzaldehyde and indole followed by iodocyclization in a one‐pot cascade process. A wide range of 2‐(substituted phenylethynyl)benzaldehydes and indoles were utilized in this protocol to derive a diverse range of iodo‐substituted tetracyclic indole fused azulene derivatives in moderate to good yields. Further functionalizations of the iodo‐substituted tetracyclic indole fused azulenes were achieved by various palladium‐catalyzed cross‐coupling reactions to generate highly substituted tetracyclic indole fused azulene derivatives.magnified image