1-(己-1-炔-1-基)-2-(甲氧基甲氧基)苯 | 125345-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(己-1-炔-1-基)-2-(甲氧基甲氧基)苯
• 英文名称: 1-hexynyl-2-(methoxymethoxy)benzene
• 英文别名: 1-Hex-1-ynyl-2-(methoxymethoxy)benzene
• CAS: 125345-26-8
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: XBEMRAPJRNMPIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1-(己-1-炔-1-基)-2-(甲氧基甲氧基)苯 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 2-丁基苯并呋喃
  参考文献：
  名称：

  Highly efficient heterogeneous synthesis of benzofurans under aqueous condition

  摘要：

  Highly efficient organic reactions in water are important for designing environmental-friendly and low cost synthetic processes. Herein, we demonstrate an intermediate-in-water strategy for the heterogeneous synthesis of benzofurans in aqueous media. The cyclization reaction of 2-(phenylethynyl)phenol to 2-phenylbenzofuran cannot proceed in pure water. However, this reaction can be efficiently promoted by the formation of sparingly soluble intermediate in the presence of alkaline. Quantitative conversion of a variety of substrates to benzofuran derivatives has been achieved in the absence of noble metal catalyst. Other remarkable features including easy-isolation and purification of product, along with wide range of functional group tolerance render the methodology promising in the realm of green-synthesis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.005
• 作为产物：
  描述：

  2-碘苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 1-(己-1-炔-1-基)-2-(甲氧基甲氧基)苯
  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

• Condensed heteroaromatic ring systems. XXIV. Palladium-catalyzed cyclization of 2-substituted phenylacetylenes in the presence of carbon monoxide
  作者：Yoshinori Kondo、Futoshi Shiga、Naoko Murata、Takao Sakamoto、Hiroshi Yamanaka

  DOI：10.1016/s0040-4020(01)89295-4

  日期：1994.1

  The palladium-catalyzed reaction of 2-alkynylanilines and 2-alkynylphenols in the presence of carbon monoxide and methanol under basic conditions gave the sequential cyclization / carbonylation products, methyl 2-substituted indole and benzo[b]-furan-3-carboxylates. Similar reaction of 2-alkynylbenzamides gave 3-alkylidenisoindole derivatives.

  在碱性条件下，在一氧化碳和甲醇存在下，钯催化的2-炔基苯胺和2-炔基苯酚的反应，依次得到环化/羰基化产物，2-甲基取代的吲哚和苯并[ b ]-呋喃-3-羧酸酯。2-炔基苯甲酰胺的类似反应得到3-亚烷基亚异吲哚衍生物。
• Visible-Light-Driven Alkyne Hydro-/Carbocarboxylation Using CO₂via Iridium/Cobalt Dual Catalysis for Divergent Heterocycle Synthesis
  作者：Jing Hou、Aloysius Ee、Wei Feng、Jin-Hui Xu、Yu Zhao、Jie Wu

  DOI：10.1021/jacs.8b01561

  日期：2018.4.18

  We present herein the first visible-light-driven hydrocarboxylation as well as carbocarboxylation of alkynes using CO2 via an iridium/cobalt dual catalysis. Such transformations provide access to various pharmaceutically important heterocycles in a one-pot procedure from readily available alkynes. Coumarins, 2-quinolones, and 2-benzoxepinones were directly accessed through a one-pot alkyne hydrocarboxylation/alkene

  我们在此展示了第一个可见光驱动的烃羧化以及通过铱/钴双催化使用 CO2 的炔烃的羧化。这种转化提供了通过一锅法从容易获得的炔烃获得各种药学上重要的杂环的途径。通过一锅炔烃加氢羧化/烯烃异构化/环化序列直接获得香豆素、2-喹诺酮和 2-苯并氧杂环酮，其中 Ir 光催化剂起到双重作用，促进炔烃加氢羧化中的单电子转移和随后的能量转移烯烃异构化。此外，前所未有的钴羧化/酰基迁移级联使炔双官能化能够高效引入γ-羟基丁烯内酯。
• Rhodium-Catalyzed Olefin Isomerization/Enantioselective Intramolecular Alder-Ene Reaction Cascade
  作者：Ryuichi Okamoto、Eri Okazaki、Keiichi Noguchi、Ken Tanaka

  DOI：10.1021/ol201986e

  日期：2011.9.16

  The olefin isomerization/enantioselective intramolecular Alder-ene reaction cascade was achieved by using a cationic rhodium(I)/(R)-BINAP complex as a catalyst. A variety of substituted dihydrobenzofurans and dihydronaphthofurans were obtained from phenol- or naphthol-linked 1,7-enynes, respectively, with good yields and ee values.
• Gold-Catalyzed Cyclizations of (<i>o</i>-Alkynyl)phenoxyacrylates with External Nucleophiles: Regio- and Stereoselective Synthesis of Functionalized Benzo[<i>b</i>]oxepines
  作者：Jun Liu、Yuanhong Liu

  DOI：10.1021/ol302252h

  日期：2012.9.21

  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.
• Yoneda, Eiji; Sugioka, Takashi; Hirao, Kojiro, Journal of the Chemical Society. Perkin transactions I, 1998, # 3, p. 477 - 483
  作者：Yoneda, Eiji、Sugioka, Takashi、Hirao, Kojiro、Zhahg, Shi-Wei、Takahashi, Shigetoshi

  DOI：——

  日期：——