acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal
• 英文别名: 1-(1-ethoxyethoxy)-2-phenylethynylbenzene；1-(1-Ethoxyethoxy)-2-(2-phenylethynyl)benzene；1-(1-ethoxyethoxy)-2-(2-phenylethynyl)benzene
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: DCJLTQIXLAZRPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal 在 三氟化硼乙醚 、 bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 生成 3-碘-2-苯基-苯并呋喃
  参考文献：
  名称：

  具有2-取代的苯并[b]呋喃的9Z-视黄酸类似物的合成和生物学评估。

  摘要：

  2-取代的3-碘苯并[b]呋喃和锡烷基酯的钯催化的交叉偶联反应以良好的收率提供了9Z-视黄酸酯类似物的立体选择性生产。然后将这些酯通过碱性水解以优异的产率转化为相应的酸，并对其生物活性进行了评估。该类似物将多烯侧链的连接位置从苯并[b]呋喃的2-位改变为3-位，大大降低了生物活性，并且在2-位引入各种取代基几乎对活性没有影响。

  DOI：

  10.1248/cpb.58.418
• 作为产物：
  描述：

  acetaldehyde o-iodophenyl ethyl acetal 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal
  参考文献：
  名称：

  具有独特动态荧光“开/关”特性的二氧杂膦稠合双磷酸环的三组分合成

  摘要：

  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。

  DOI：

  10.1002/anie.202215436

文献信息

• Iodocyclization of Ethoxyethyl Ethers to Alkynes: A Broadly Applicable Synthesis of 3-Iodobenzo[<i>b</i>]furans
  作者：Takashi Okitsu、Daisuke Nakazawa、Rie Taniguchi、Akimori Wada

  DOI：10.1021/ol8020463

  日期：2008.11.6

  A wide variety of 3-iodobenzo[b]furans were readily prepared by iodocyclization of 2-alkynyl-1-(1-ethoxyethoxy) benzenes with the I(Coll)(2)PF6-BF3 center dot OEt2 combination. Aryl-, vinylic-, and alkyl-substituted alkynes undergo iodocyclization in good to excellent yields. The mechanism of the reaction is also discussed.
• Synthesis of 2,3-Disubstituted Benzofurans by Platinum−Olefin-Catalyzed Carboalkoxylation of <i>o</i>-Alkynylphenyl Acetals
  作者：Itaru Nakamura、Yuya Mizushima、Yoshinori Yamamoto

  DOI：10.1021/ja055202f

  日期：2005.11.1

  The PtCl2-catalyzed cyclization reaction of o-alkynylphenyl acetals 1 in the presence of 1,5-cyclooctadiene produces 3-(alpha-alkoxyalkyl)benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl)phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl)phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal (1f) in the presence of 2 mol % of platinum(II) chloride and 8 mol % of 1,5-cyclooctadiene in toluene at 30 degrees C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively.
• Synthesis of 2,3-disubstituted benzofurans and indoles by π-Lewis acidic transition metal-catalyzed cyclization of ortho-alkynylphenyl O,O- and N,O-acetals
  作者：Itaru Nakamura、Yuya Mizushima、Uichiro Yamagishi、Yoshinori Yamamoto

  DOI：10.1016/j.tet.2007.03.039

  日期：2007.8

  The PtCl2-catalyzed cyclization reaction of ortho-alkynylphenyl acetals 1 in the presence of COD (1,5-cyclooctadiene) produces 3-(alpha-alkoxyalkyl) benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl) phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl) phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl) phenyl acetal (1f) in the presence of 2 mol% of platinum(II) chloride and 8 mol% of 1,5-cycloocatadiene in toluene at 30 degrees C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively. Moreover, the reaction of N-methoxymethyl-2-alkynylanilines 3 was catalyzed by PdBr2, affording the corresponding 2,3-disubstituted indoles 4 in moderate yields. For example, the reaction of N-methoxymethyl-2-(1-pentynyl)- N-tosylaniline (3a) and N-methoxymethyl-2-(phenylethynyl)-N-tosylaniline (3b) in the presence of 10 mol% of PdBr2 in toluene at 80 degrees C gave 3-methoxymethyl-2-propyl-1-tosylindole (4a) and 3-methoxymethyl-2-phenyl-1-tosylindole (4b) in 33 and 33% yields, respectively. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of 9Z-Retinoic Acid Analogs Having 2-Substituted Benzo[b]furan
  作者：Takashi Okitsu、Daisuke Nakazawa、Kimie Nakagawa、Toshio Okano、Akimori Wada

  DOI：10.1248/cpb.58.418

  日期：——

  3-iodobenzo[b]furans and stannanyl ester afforded the stereoselective production of 9Z-retinoic acid ester analogs in good yields. These esters were then converted to the corresponding acids via basic hydrolysis in excellent yields, and their biological activities were evaluated. The analog changed the connected position of polyene side chain from 2-position to 3-position of benzo[b]furan decreased the

  2-取代的3-碘苯并[b]呋喃和锡烷基酯的钯催化的交叉偶联反应以良好的收率提供了9Z-视黄酸酯类似物的立体选择性生产。然后将这些酯通过碱性水解以优异的产率转化为相应的酸，并对其生物活性进行了评估。该类似物将多烯侧链的连接位置从苯并[b]呋喃的2-位改变为3-位，大大降低了生物活性，并且在2-位引入各种取代基几乎对活性没有影响。
• 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。