(E)-2-nitro-1,4-diphenylbut-1-en-3-yne

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (E)-2-nitro-1,4-diphenylbut-1-en-3-yne
• 英文别名: [(E)-2-nitro-4-phenylbut-1-en-3-ynyl]benzene
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: MIIYDHKRBBASLY-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-nitro-1,4-diphenylbut-1-en-3-yne 在 ammonium hydroxide 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以52%的产率得到3-iodo-4-nitro-2,5-diphenyl-1H-pyrrole
  参考文献：
  名称：

  A Novel Tandem Sequence to Pyrrole Syntheses by 5-endo-dig Cyclization of 1,3-Enynes with Amines

  摘要：

  The synthesis of pentasubstituted pyrroles has been described using molecular iodine from 1,3-enynes and amines via a sequential tandem aza-Michael addition, iodocyclization, and oxidative aromatization. The protocol is simple and efficient to afford the target products at ambient conditions.

  DOI：

  10.1021/ol402305b
• 作为产物：
  描述：

  苯甲醛 在 copper(l) iodide 、 ammonium acetate 、 溴 、 sodium acetate 作用下， 以 氯仿 、 溶剂黄146 、 甲苯 为溶剂， 反应 0.5h， 生成 (E)-2-nitro-1,4-diphenylbut-1-en-3-yne
  参考文献：
  名称：

  A Novel Tandem Sequence to Pyrrole Syntheses by 5-endo-dig Cyclization of 1,3-Enynes with Amines

  摘要：

  The synthesis of pentasubstituted pyrroles has been described using molecular iodine from 1,3-enynes and amines via a sequential tandem aza-Michael addition, iodocyclization, and oxidative aromatization. The protocol is simple and efficient to afford the target products at ambient conditions.

  DOI：

  10.1021/ol402305b
• 作为试剂：
  描述：

  1-(三氟甲基)-1,2-苯碘酰-3(1H)-酮 、 2,2,6,6-四甲基哌啶氧化物 在 (E)-2-nitro-1,4-diphenylbut-1-en-3-yne 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 、 乙烷,三氯氟- 、 calcium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以51%的产率得到2,2,6,6-tetramethyl-1-(trifluoromethoxy)piperidine
  参考文献：
  名称：

  通过Cu（II）/ Rh（III）促进的Aza-Michael加成/三氟甲基化环化/氧化反应的三组分级联合成完全取代的三氟甲基吡咯。

  摘要：

  已开发出一种由1,3-炔烃，苯胺和Togni-II试剂组成的三组分级联反应，可在温和条件下以高区域选择性提供完全取代的三氟甲基吡咯。所述转化通过Cu（II）/ Rh（III）促进的级联氮杂-Michael加成/三氟甲基化环化/氧化反应进行，得到三氟甲基吡咯衍生物作为主要产物。

  DOI：

  10.1021/acs.joc.9b03470

文献信息

• Organocatalytic Enantioselective Tandem Michael Addition and Cyclization Reaction of Trisubstituted 2-Nitro-1,3-enynes with Cyclic 1,3-Diketones
  作者：Zi-Min Xing、Le-Le Song、Feng-Xing Li、Nian-Sheng Xu、Lu-Feng Wang、Zi-Fa Shi、Xiao-Ping Cao

  DOI：10.1002/adsc.201700085

  日期：2017.6.6

  An enantioselective tandem Michael addition/cyclization reaction between trisubstituted 2‐nitro‐1,3‐enynes and cyclic 1,3‐diketones catalyzed by a chiral organosquaramide catalyst in the presence of Ag2CO3 was developed. The chiral functionalized chromene products could be obtained in good yield and in 80–99% enantiomeric excess. The structures and absolute configurations of some of the products were

  在Ag 2 CO 3存在下，通过手性有机方酰胺催化剂催化三取代的2-硝基-1,3-烯炔与环状的1,3-二酮之间的对映选择性串联迈克尔加成/环化反应。手性官能化的色烯产品可以以良好的收率和80-99％的对映异构体过量获得。X射线晶体学分析证实了某些产品的结构和绝对构型。
• Enantioselective access to tetrahydropyrano[2,3- c ]pyrazoles via an organocatalytic domino Michael-hydroalkoxylation reaction
  作者：Nirmal K. Rana、Rupesh K. Jha、Harshit Joshi、Vinod K. Singh

  DOI：10.1016/j.tetlet.2017.04.059

  日期：2017.5

  An asymmetric domino Michael-hydroalkoxylation reaction of trans-α-alkynyl-nitroolefins with N-arylpyrazolinones has been accomplished using a chiral bifunctional squaramide catalyst. Under the organocatalytic method, a broad range of tetrahydropyrano[2,3-c]pyrazoles with an exocyclic alkene at the C-6 position were prepared in high yields and excellent stereoselectivities. The presence of an exocyclic

  反式-α-炔基-硝基烯烃与N-芳基吡唑啉酮类的不对称多米诺迈克尔-氢化烷氧基化反应已使用手性双功​​能方酰胺催化剂完成。在有机催化方法下，可以高产率和出色的立体选择性制备各种在C-6位带有环外烯烃的四氢吡喃并[2,3- c ]吡唑。吡喃并吡唑中存在环外双键和硝基为进一步的结构转化提供了广阔的空间。
• DABCO catalyzed domino Michael/hydroalkoxylation reaction involving α-alkynyl-β-aryl nitroolefins: excellent stereoselective access to dihydropyrano[3,2-c]chromenes, pyranonaphthoquinones and related heterocycles
  作者：Soumen Biswas、Anuradha Dagar、Shaikh M. Mobin、Sampak Samanta

  DOI：10.1039/c5ob02400e

  日期：——

  Excellent stereoselective (up to ≤96 : 4 Z/E ratio) construction of pharmaceutically interesting functionalized pyrano[3,2-c]chromenes, pyranonaphthoquinones and related pyrano-fused heterocycles has been achieved in good to high yields (72–89%) through a domino Michael/hydroalkoxylation reaction involving several enolizable cyclic β-keto esters/1,3-dicarbonyls and α-arylacetylenyl-β-nitrostyrenes

  具有良好的高收率（72–89％），可实现药学上有趣的官能化吡喃并[3,2- c ]色烯，吡喃并萘醌和相关的吡喃并稠合杂环的出色立体选择性（最高≤96：4 Z / E比）结构。在室温下，使用DABCO作为有机催化剂，在EtOH中通过涉及多个可烯化的环状β-酮酯/ 1,3-二羰基和α-芳基乙炔基-β-硝基苯乙烯的多米诺尔迈克尔/加氢烷氧基化反应。此外，顺式-2-苄基-4-芳基-3,4-二氢吡喃并[3,2- c ^ ]以高产率（81-86％），得到色烯经由相应的2-亚苄基-3,4-的立体选择性denitrohydrogenation -二氢吡喃[3,2-c ]色烯，催化量为10％Pd / C。
• Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines
  作者：Ganesan Bharathiraja、Mani Sengoden、Masanam Kannan、Tharmalingam Punniyamurthy

  DOI：10.1039/c4ob02508c

  日期：——

  Various tetrasubstituted pyrroles/pyrazoles have been prepared from nitro-substituted 1,3-enynes with aromatic amines/hydrazinesviaa copper-catalyzed cascade aza-Michael addition, cyclization and aromatization.

  利用芳香胺/肼和含硝基的1,3-烯烃，通过铜催化级联氮-迈克尔加成、环化和芳香化反应，制备了多种四取代吡咯/吡唑。
• Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes
  作者：Madhu Ganesh、Irishi N.N. Namboothiri

  DOI：10.1016/j.tet.2007.09.012

  日期：2007.11

  (Z)-alpha-Bromo-beta-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)(4) as catalyst to afford (E)-alpha,beta-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of alpha-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful alpha,beta-disubstituted nitroethylenes. (c) 2007 Elsevier Ltd. All rights reserved.