2-((4-(tert-butyl)phenyl)ethynyl)-5-methoxybenzaldehyde | 1448038-54-7

• 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-((4-(tert-butyl)phenyl)ethynyl)-5-methoxybenzaldehyde
• 英文别名: 2-[2-(4-Tert-butylphenyl)ethynyl]-5-methoxybenzaldehyde；2-[2-(4-tert-butylphenyl)ethynyl]-5-methoxybenzaldehyde
• CAS: 1448038-54-7
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: DAJPXGPLFRPRKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-((4-(tert-butyl)phenyl)ethynyl)-5-methoxybenzaldehyde 在 chloro(triphenylphosphine)gold(I)-silver hexafluoroantimonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.34h， 生成 9-[4-(tert-butyl)phenyl]-13-methoxy-14b,16-dihydroindolo[3′,4′:3,4,5]pyrido[2′,3′:6,7]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：

  4-叔-丁基苯基乙炔 、 2-溴-5-甲氧基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 生成 2-((4-(tert-butyl)phenyl)ethynyl)-5-methoxybenzaldehyde
  参考文献：
  名称：

  （Z，Z）-异苯并呋喃的立体定向合成通过自由基激活的C（sp3）-C（sp3）和C（sp2）-卤素键的裂解

  摘要：

  β-炔基酮与卤代芳基重氮四氟硼酸酯和DABCO自由基引发的新型环化/ 1,8-卤代磺酰化反应。bis（二氧化硫）首先通过C（sp 3）-C（sp 3）和C（sp 2）-卤素键的裂解/重组而获得，其中47个实例为含砜的1,3-二亚甲基取代基（Z，Z）-异苯并呋喃为单一立体异构体，通常收率良好。提议该多组分途径通过原位进行生成芳基磺酰基自由基，然后进行选择性丙基加成环化和环丙基单元的开环以及C（sp 2）-卤素键裂解，从而连续构建了三个新的化学键，包括CS，C -O和C-卤素键。

  DOI：

  10.1002/adsc.201900729

文献信息

• Metal-Free Decarboxylative Cyclization/Ring Expansion: Construction of Five-, Six-, and Seven-Membered Heterocycles from 2-Alkynyl Benzaldehydes and Cyclic Amino Acids
  作者：Srinivas Samala、Gajendra Singh、Ravi Kumar、Ravi Sankar Ampapathi、Bijoy Kundu

  DOI：10.1002/anie.201504429

  日期：2015.8.10

  A one pot synthesis of 1H‐benzo[g]indoles, tetrahydrobenzo[h]quinolines, and naphtho[1,2‐b]azepines from 2‐alkynyl benzaldehydes and cyclic amino acids is reported. The salient feature of the strategy involves formation of three new bonds (one CN and two CC bonds) by a metal‐free decarboxylation/cyclization/one‐carbon ring expansion sequence in one pot.

  据报道，由2-炔基苯甲醛和环状氨基酸一锅合成1 H-苯并[g]吲哚，四氢苯并[h]喹啉和萘并[1,2-b]氮杂。该策略的显着特征是通过在一个罐中进行无金属脱羧/环化/一碳环扩环来形成三个新键（一个CN和两个CC键）。
• 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.
• Stereospecific Synthesis of ( <i>Z</i> , <i>Z</i> )‐Isobenzofurans <i>via</i> Radical‐Enabled Cleavage of C( <i>sp</i> ³ )−C( <i>sp</i> ³ ) and C( <i>sp</i> ² )‐Halogen Bonds
  作者：Min‐Hua Huang、Hao‐Nan Shi、Chi‐Fan Zhu、Chun‐Lan He、Wen‐Juan Hao、Shu‐Jiang Tu、Bo Jiang

  DOI：10.1002/adsc.201900729

  日期：2019.12.3

  8‐halosulfonylation of β‐alkynyl ketones with haloaryl diazonium tetrafluoroborates and DABCO.bis(sulfur dioxide) was first achieved via the cleavage/recombination of C(sp3)−C(sp3) and C(sp2)‐halogen bonds, from which 47 examples of sulfone‐containing 1,3‐dimethylene‐substituted (Z,Z)‐isobenzofurans as single stereoisomers were synthesized in generally good yields. This multicomponent pathway is proposed to

  β-炔基酮与卤代芳基重氮四氟硼酸酯和DABCO自由基引发的新型环化/ 1,8-卤代磺酰化反应。bis（二氧化硫）首先通过C（sp 3）-C（sp 3）和C（sp 2）-卤素键的裂解/重组而获得，其中47个实例为含砜的1,3-二亚甲基取代基（Z，Z）-异苯并呋喃为单一立体异构体，通常收率良好。提议该多组分途径通过原位进行生成芳基磺酰基自由基，然后进行选择性丙基加成环化和环丙基单元的开环以及C（sp 2）-卤素键裂解，从而连续构建了三个新的化学键，包括CS，C -O和C-卤素键。
• 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.