2-(cyclohex-1-en-1-ylethynyl)-5-methoxybenzaldehyde | 1404078-24-5

• 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: 2-(cyclohex-1-en-1-ylethynyl)-5-methoxybenzaldehyde
• 英文别名: 2-[2-(Cyclohexen-1-yl)ethynyl]-5-methoxybenzaldehyde；2-[2-(cyclohexen-1-yl)ethynyl]-5-methoxybenzaldehyde
• CAS: 1404078-24-5
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: AYNXWUYWBMCYLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(cyclohex-1-en-1-ylethynyl)-5-methoxybenzaldehyde 在 chloro(triphenylphosphine)gold(I)-silver hexafluoroantimonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.34h， 生成 9-(cyclohex-1-en-1-yl)-13-methoxy-5-methyl-14b,16-dihydrobenzo[6,7]indolo[3′,4′:3,4,5]azepino[2,1-a]isoquinoline
  参考文献：
  名称：

  A Sequential One-Pot Protocol for the Synthesis of Dihydrobenzo[6,7]indolo-[3′,4′:3,4,5]azepino[2,1-a]isoquinolines Using a Gold-Silver Combined Catalyst

  摘要：

  A sequential one-pot protocol for the synthesis of indole-based peri-annulated polyheterocycles using trifluoroacetic acid and a gold-silver combined catalyst system is described. The reaction is thought to proceed via an imine formation-cationic pi-cyclization-alkyne activation-intramolecular hydroamination sequence to yield novel dihydrobenzo[6,7]indolo[3',4':3,4,5]azepino[2,1-a]isoquinolines in good yields.

  DOI：

  10.1055/s-0033-1338424
• 作为产物：
  描述：

  1-乙炔基环己烷 、 2-溴-5-甲氧基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以87%的产率得到2-(cyclohex-1-en-1-ylethynyl)-5-methoxybenzaldehyde
  参考文献：
  名称：

  A Sequential One-Pot Protocol for the Synthesis of Dihydrobenzo[6,7]indolo-[3′,4′:3,4,5]azepino[2,1-a]isoquinolines Using a Gold-Silver Combined Catalyst

  摘要：

  A sequential one-pot protocol for the synthesis of indole-based peri-annulated polyheterocycles using trifluoroacetic acid and a gold-silver combined catalyst system is described. The reaction is thought to proceed via an imine formation-cationic pi-cyclization-alkyne activation-intramolecular hydroamination sequence to yield novel dihydrobenzo[6,7]indolo[3',4':3,4,5]azepino[2,1-a]isoquinolines in good yields.

  DOI：

  10.1055/s-0033-1338424

文献信息

• Ag(I)-Catalyzed Aminofluorination of Alkynes: Efficient Synthesis of 4-Fluoroisoquinolines and 4-Fluoropyrrolo[α]isoquinolines
  作者：Tao Xu、Guosheng Liu

  DOI：10.1021/ol3026507

  日期：2012.11.2

  A silver-catalyzed intramolecular oxidative aminofluorination of alkynes has been developed by using NFSI as a fluorinating reagent. This reaction represents an efficient method for the synthesis of various 4-fluoroisoquinolines and 4-fluoropyrrolo[α]isoquinolines.

  通过使用NFSI作为氟化试剂，开发了炔烃的银催化的分子内氧化氨基氟化。该反应代表了合成各种4-氟异喹啉和4-氟吡咯并[α]异喹啉的有效方法。
• Iodine-mediated electrophilic tandem cyclization of 2-alkynylbenzaldehydes with anthranilic acid leading to 1,2-dihydroisoquinoline-fused benzoxazinones
  作者：Shashikant U. Dighe、Sanjay Batra

  DOI：10.1016/j.tet.2013.08.086

  日期：2013.11

  An efficient iodine-mediated electrophilic tandem cyclization of substituted 2-alkynylbenzaldehydes with anthranilic acids under basic medium leading to iodo-1,2-dihydroisoquinoline-fused benzoxazinones is presented. Success of the protocol for the reaction of substituted 2-alkynylbenzaldehydes with 2-aminobenzamides to furnish isoquinoline-fused quinazolinones is also described.

  一种有效碘介导的亲电串联取代的2- alkynylbenzaldehydes与邻氨基苯甲酸的下基本培养基环化导致碘-1,2-二氢异喹啉稠合苯并嗪酮被呈现。该协议为取代的2- alkynylbenzaldehydes与2-氨基苯甲酰胺，得到异喹啉稠合喹唑啉酮反应的成功也被描述。
• Three-Component Tandem-Intramolecular Hydroamination Reactions in One Pot Involving Indoles, 2-Aminobenzyl Alcohols, and 2-Alkynylbenzaldehydes: Consecutive 7-<i>endo</i>-<i>trig</i>and Electrophilic 6-<i>endo</i>-<i>dig</i>Cyclizations
  作者：Srinivas Samala、Mohammad Saifuddin、Anil K. Mandadapu、Bijoy Kundu

  DOI：10.1002/ejoc.201300100

  日期：2013.6

  A one-pot protocol for the synthesis of indole-based annulated polyheterocycles involving consecutive 7-endo-trig and electrophilic 6-endo-dig cyclizations is described. The reaction proceeds initially through annulation of 5-methoxyindole, 2-amino benzyl alcohol and 2-alkynylbenzaldehyde

  描述了一种用于合成基于吲哚的环状聚杂环的一锅协议，涉及连续的 7-endo-trig 和亲电 6-endo-dig 环化。该反应最初通过 5-甲氧基吲哚、2-氨基苯甲醇和 2-炔基苯甲醛的环化进行
• Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynylbenzaldehyde via Domino Reactions under Transition-Metal-Free Conditions
  作者：Rajesh K. Arigela、Srinivas Samala、Rohit Mahar、Sanjeev K. Shukla、Bijoy Kundu

  DOI：10.1021/jo401929q

  日期：2013.10.18

  We describe two simple straightforward syntheses of triazolo isoquinolines (3) and isochromenes (7) from 2-alkynylbenzaldehydes (1) as a common synthon. The synthetic strategy for 3 involves formation of the (E)-1-(2-nitrovinyl)-2-(alkynyl)benzene species 2 via condensation of synthon 1 with nitromethane followed by a [3 + 2] cycloaddition/extrusion of the nitro group/regioselective 6-endo cyclization domino sequence. In yet another strategy, the synthon 1 was condensed with nitromethane followed by electrophilic iodo cyclization of the resulting 2-nitro-1-(2-(alkynyl)phenyl)ethanol (6) to furnish iodo isochromene derivatives. The salient feature of the above two strategies involves formation of the corresponding heterocycles under metal-free conditions in good yields.
• A Sequential One-Pot Protocol for the Synthesis of Dihydrobenzo[6,7]indolo-[3′,4′:3,4,5]azepino[2,1-a]isoquinolines Using a Gold-Silver Combined Catalyst
  作者：Bijoy Kundu、Mohammad Saifuddin、Srinivas Samala、Deevi Krishna

  DOI：10.1055/s-0033-1338424

  日期：——

  A sequential one-pot protocol for the synthesis of indole-based peri-annulated polyheterocycles using trifluoroacetic acid and a gold-silver combined catalyst system is described. The reaction is thought to proceed via an imine formation-cationic pi-cyclization-alkyne activation-intramolecular hydroamination sequence to yield novel dihydrobenzo[6,7]indolo[3',4':3,4,5]azepino[2,1-a]isoquinolines in good yields.