ethyl 2-(5-ethyl-2-hydroxyphenyl)-2-oxoacetate | 1380745-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(5-ethyl-2-hydroxyphenyl)-2-oxoacetate
• CAS: 1380745-74-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: ZPXVPQCJJHITCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-Chlorphenyl-allenyl-sulfon 、 ethyl 2-(5-ethyl-2-hydroxyphenyl)-2-oxoacetate 在 sodium 4-methylbenzenesulfinate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以34%的产率得到ethyl (Z)-2-(((4-chlorophenyl)sulfonyl)methylene)-6-ethyl-4-hydroxychromane-4-carboxylate
  参考文献：
  名称：

  Synthesis of quaternary carbon centered chromans from the reactions of ethyl 2-(2-hydroxyaryl)-2-oxoacetates with allenic ester or allenic sulfone catalyzed by tertiary phosphine and SPTS

  摘要：

  Cyclization reactions of ethyl 2-(2-hydroxyaryl)-2-oxoacetates with ethyl 2,3-butadienoate and allenylsulfone proceeded smoothly in the presence of tertiary phosphine and sodium p-toluenesulfinate (SFTS) to give the corresponding quaternary carbon centered chromans in moderate to good yields under mild conditions, which provides an alternative efficient approach for the synthesis of biologically active chroman products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.036
• 作为产物：
  描述：

  4-乙基苯酚 、 草酰氯单乙酯 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl 2-(5-ethyl-2-hydroxyphenyl)-2-oxoacetate
  参考文献：
  名称：

  Synthesis of quaternary carbon centered chromans from the reactions of ethyl 2-(2-hydroxyaryl)-2-oxoacetates with allenic ester or allenic sulfone catalyzed by tertiary phosphine and SPTS

  摘要：

  Cyclization reactions of ethyl 2-(2-hydroxyaryl)-2-oxoacetates with ethyl 2,3-butadienoate and allenylsulfone proceeded smoothly in the presence of tertiary phosphine and sodium p-toluenesulfinate (SFTS) to give the corresponding quaternary carbon centered chromans in moderate to good yields under mild conditions, which provides an alternative efficient approach for the synthesis of biologically active chroman products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.036

文献信息

• P^III-Mediated intramolecular cyclopropanation and metal-free synthesis of cyclopropane-fused heterocycles
  作者：Jiayong Zhang、Jiahang Hao、Zhiqiang Huang、Jie Han、Zhengjie He

  DOI：10.1039/d0cc04086j

  日期：——

  A P(NMe2)3-mediated reductive intramolecular cyclopropanation is developed for the first time, which provides facile access to a wide variety of cyclopropane-fused heterocycles including chromanes, tetrahydroquinolines, lactones, and lactams. Catalytic hydrogenative ring-expansion of the cyclopropane-fused heterocycles is also elaborated, leading to various structurally important medium-sized heterocycles

  首次开发了AP（NMe 2）3介导的还原性分子内环丙烷化反应，该反应可轻松利用各种环丙烷稠合的杂环，包括苯并二氢吡喃，四氢喹啉，内酯和内酰胺。还详细说明了环丙烷稠合杂环的催化加氢扩环，从而产生了各种结构上重要的中等尺寸的杂环。
• Lewis Base-Catalyzed Intramolecular Vinylogous Aldol Reaction and Chemoselective Syntheses of 3-Hydroxy-2,3-Disubstituted Dihydrobenzofurans and Indolines
  作者：Jiayong Zhang、Zhengjie He

  DOI：10.1021/acs.joc.3c01313

  日期：2023.9.15

  A Lewis base-catalyzed intramolecular vinylogous aldol reaction of o-(allyloxy)phenyl ketoesters or o-(allylamino)phenyl ketoesters has been developed. This reaction provides ready access to 3-hydroxy-2,3-disubstituted dihydrobenzofurans and indolines in high yields with excellent chemoselectivity and diastereoselectivity. An acid-promoted dehydration of such products further extends the utility of

  开发了路易斯碱催化的邻-(烯丙氧基)苯基酮酯或邻-(烯丙氨基)苯基酮酯的分子内插烯羟醛反应。该反应可以以高产率轻松获得 3-羟基-2,3-二取代的二氢苯并呋喃和二氢吲哚，并具有优异的化学选择性和非对映选择性。此类产物的酸促进脱水进一步将该反应的用途扩展到2-烯基苯并呋喃和吲哚的合成。