ethyl 4-((2-hydroxyphenyl)ethynyl)benzoate | 1338699-34-5

• 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 4-((2-hydroxyphenyl)ethynyl)benzoate
• 英文别名: Ethyl 4-[2-(2-hydroxyphenyl)ethynyl]benzoate
• CAS: 1338699-34-5
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: JPMSADVBYPFEOB-UHFFFAOYSA-N

物化性质

• 沸点：
  424.6±30.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-((2-hydroxyphenyl)ethynyl)benzoate 在 三乙烯二胺 、 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 methyl (2SR,3SR)-2-butoxy-4-(4-(ethoxycarbonyl)phenyl)-2,3-dihydrobenzo[b]oxepine-3-carboxylate
  参考文献：
  名称：

  Gold-Catalyzed Cyclizations of (o-Alkynyl)phenoxyacrylates with External Nucleophiles: Regio- and Stereoselective Synthesis of Functionalized Benzo[b]oxepines

  摘要：

  A catalytic approach to benzo[b]oxepines with high stereoselectivity by Au-catalyzed cyclization of (o-alkynyl)phenoxyacrylates with various nucleophiles under mild reaction conditions has been developed. Notably, the use of vinyl ether instead of alcohol could afford the same benzoxepines. The reaction may proceed by Au-catalyzed oligomerization of vinyl ether to release the alcohol, which then reacts with (o-alkynyl)phenoxyacrylates to furnish the benzoxepines.

  DOI：

  10.1021/ol302252h
• 作为产物：
  描述：

  1-乙炔基-2-(甲氧基甲氧基)苯 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 生成 ethyl 4-((2-hydroxyphenyl)ethynyl)benzoate
  参考文献：
  名称：

  Gold-Catalyzed Cyclizations of (o-Alkynyl)phenoxyacrylates with External Nucleophiles: Regio- and Stereoselective Synthesis of Functionalized Benzo[b]oxepines

  摘要：

  A catalytic approach to benzo[b]oxepines with high stereoselectivity by Au-catalyzed cyclization of (o-alkynyl)phenoxyacrylates with various nucleophiles under mild reaction conditions has been developed. Notably, the use of vinyl ether instead of alcohol could afford the same benzoxepines. The reaction may proceed by Au-catalyzed oligomerization of vinyl ether to release the alcohol, which then reacts with (o-alkynyl)phenoxyacrylates to furnish the benzoxepines.

  DOI：

  10.1021/ol302252h

文献信息

• Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Br<scp>ø</scp>nsted base
  作者：Azusa Kondoh、Hoa Thi Quynh Tran、Kyoko Kimura、Masahiro Terada

  DOI：10.1039/c6cc01690a

  日期：——

  An enantioselective intramolecular cyclization reaction of alkynyl esters was developed, which employs a Bronsted base catalyst generated in situ from a chiral Schiff base and t-BuOK. This reaction is a...

  开发了炔基酯的对映选择性分子内环化反应，该反应使用了从手性席夫碱和t-BuOK原位生成的布朗斯台德碱催化剂。这个反应是...
• A New Insight into Palladium-Catalyzed Reaction of 2-Alkynylphenol with Carbon Monoxide
  作者：Yong Luo、Jie Wu

  DOI：10.1021/ol202478u

  日期：2011.11.4

  A novel and efficient pathway for the generation of 3-(benzofuran-3-ylmethylene)benzofuran-2(3H)-ones via a palladium-catalyzed carbonylative reaction of 2-alkynylphenol with carbon monoxide is described. The reaction proceeds through a double insertion of triple bonds during the reaction process. The products are obtained in good yields with high selectivity. A one-pot synthesis starting from 2-iodophenol

  描述了通过钯催化的2-炔基苯酚与一氧化碳的羰基化反应生成3-（苯并呋喃-3-基亚甲基）苯并呋喃-2（3 H）-的新颖而有效的途径。反应在反应过程中通过三键的两次插入而进行。以高收率和高选择性获得产物。还提出了一种从2-碘苯酚和炔烃开始的一锅法合成法。
• Three‐Component Synthesis of Dioxaphosphorane‐Fused Diphosphacycles Exhibiting Unique Dynamic Fluorescence “On/Off” Properties
  作者：Chenchen Li、Haiyang Huang、Longgen Sun、Mingqing Huang、Haixin Ding、Jiang Bai、Ban‐Peng Cao、Qiang Xiao

  DOI：10.1002/anie.202215436

  日期：2023.2

  Herein, we report a straightforward three-component synthesis of novel dioxaphosphorane-fused diphosphacycles with distinctive photophysical properties. Based on their unique structure and properties, a novel fluorescent switch for pH sensing was revealed by a dynamic ring-opening/ring-closing mechanism.

  在此，我们报告了具有独特光物理特性的新型二氧杂正膦稠合二磷酸环的直接三组分合成。基于其独特的结构和特性，通过动态开环/闭环机制揭示了一种用于 pH 传感的新型荧光开关。
• US5534641A
  申请人：——

  公开号：US5534641A

  公开（公告）日：1996-07-09
• [EN] ACETYLENES DISUBSTITUTED WITH 2-TETRAHYDROPYRANOXYARYL AND ARYL OR HETEROARYL GROUPS HAVING RETINOID-LIKE BIOLOGICAL ACTIVITY<br/>[FR] ACETYLENES DISUBSTITUES PAR DES GROUPES 2-TETRAHYDROPYRANOXYARYLES ET ARYLES OU HETEROARYLES A ACTIVITE BIOLOGIQUE ANALOGUE AUX RETINOIDES
  申请人：ALLERGAN

  公开号：WO1996020938A1

  公开（公告）日：1996-07-11

  (EN) Compounds of formula (1), wherein R1-R5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; THP is a 2-tetrahydropyranyl group; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pirimidinyl, pyrazinyl, thiazolyl and oxazolyl, said groups being substituted with the R5 group defined above; A is (CH2)n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, or CR7OR13O, where R7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R8 is phenyl or lower alkylphenyl, R9 and R10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, and R13 is divalent alkyl radical of 2-5 carbons, having retinoid-like biological activity.(FR) Composés de formule (1), dans laquelle R1 - R5 désignent indépendamment les uns des autres hydrogène, alkyle inférieur ayant 1 à 6 atomes de carbone, alkyle ou cycloalkyle à chaîne ramifiée ayant 3 à 15 atomes de carbone, cycloalkyle inférieur substitué par alkyle inférieur ayant 3 à 15 atomes de carbone; THP est un groupe 2-tétrahydro pyranyle; X désigne S ou O; Y désigne un groupe phényle ou hétéroaryle sélectionné dans un groupe constitué de pyridyle, thiényle, furyle, pyridazinyle, pirimidinyle, pyrazinyle, thiazolyle et oxazolyle, ces groupes étant substitués par le groupe R5 défini ci-dessus; A désigne (CH2)n où n vaut 0 à 5, alkyle inférieur à chaîne ramifiée ayant 3 à 6 atomes de carbone, cycloalkyle ayant 3 à 6 atomes de carbone, alcényle ayant 2 à 6 atomes de carbone et 1 ou 2 liaisons doubles, alcynyle ayant 2 à 6 atomes de carbone et 1 ou 2 liaisons triples; B désigne hydrogène, COOH ou un sel pharmaceutiquement acceptable de celui-ci, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2 ou CR7OR13O, où R7 désigne un groupe alkyle, cycloalkyle ou alcényle ayant 1 à 5 atomes de carbone, R8 désigne un groupe alkyle ayant 1 à 10 atomes de carbone ou un groupe cycloalkyle ayant 1 à 10 atomes de carbone, ou R8 désigne phényle ou alkylphényle inférieur, R9 et R10 désignent indépendamment l'un de l'autre hydrogène, un groupe alkyle ayant 1 à 10 atomes de carbone, un groupe cycloalkyle ayant 1 à 10 atomes de carbone, phényle ou alkylphényle inférieur, R11 désigne alkyle inférieur, phényle ou alkylphényle inférieur, R12 désigne alkyle inférieur et R13 désigne un radical alkyle divalent ayant 2 à 5 atomes de carbone. Ces composés ont une activité biologique analogue aux rétinoïdes.