acetaldehyde o-iodophenyl ethyl acetal | 870011-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: acetaldehyde o-iodophenyl ethyl acetal
• 英文别名: 1-(1-ethoxyethoxy)-2-iodobenzene
• CAS: 870011-18-0
• 化学式: C₁₀H₁₃IO₂
• 分子量: 292.117
• InChiKey: BSIMCZKQHTVQBG-UHFFFAOYSA-N

物化性质

• 沸点：
  305.6±27.0 °C(Predicted)
• 密度：
  1.523±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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 o-iodophenyl ethyl acetal 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.08h， 生成
  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
• 作为产物：
  描述：

  2-碘苯酚 、 乙烯基乙醚 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以68%的产率得到acetaldehyde o-iodophenyl ethyl acetal
  参考文献：
  名称：

  通过形式碳烷氧基化的金催化多米诺合成功能化的苯并呋喃和四环异色满

  摘要：

  已经开发了由α-烷氧基烷基邻炔基芳基醚（n = 0）和富电子芳烃对侧链进行修饰的苯并呋喃的多米诺合成。在目前的多米诺骨牌反应中，芳烃的α-烷氧基烷基化与邻炔基芳基醚的迁移环异构化中的中间体进行反应，然后将苯并呋喃亲核加成到苄基醚中，阳离子Au（III）催化剂活化了C- Cπ键和C–Oσ键。本方法可以扩展到由α-烷氧基烷基（邻炔基芳基）甲基醚（n＝ 1）和芳基甲氧基甲基醚的Au（I）催化的四环异色团的多米诺骨牌合成。

  DOI：

  10.1021/acs.orglett.6b02159

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.
• Catalyst composition comprising an alkylene diamine-nickel complex and process for producing a cross-coupled compound using the same
  申请人：TOSOH CORPORATION

  公开号：EP1707263B1

  公开（公告）日：2009-02-25
• Catalyst composition and process for producing cross-coupled compound using same
  申请人：Ishikawa Shinichi

  公开号：US20060224011A1

  公开（公告）日：2006-10-05

  A catalyst composition for a cross-coupling reaction comprising a nickel salt-amine complex of formula (1), and triphenylphosphine. where R 1 thru R 4 independently represent alkyl, aryl, heteroaryl or alkenyl; n is an integer of 1-6; and X independently represents halo, hydroxyl, nitrate or acetate group. Using the catalyst composition, a cross-coupling reaction is carried out between a boron-containing compound of formula (2) and a compound of formula (3). where R 5 and R 6 are the same as R 1 -R 4 defined above; Y independently represents hydroxyl or alkoxy, Z is halo, methanesulfonate or trifluoromethanesulfonate.