2-benzylidene-4-(4-nitrophenyl)-1-phenylbut-3-yn-1-one | 1172595-48-0

• 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: 2-benzylidene-4-(4-nitrophenyl)-1-phenylbut-3-yn-1-one
• CAS: 1172595-48-0
• 化学式: C₂₃H₁₅NO₃
• 分子量: 353.377
• InChiKey: ZADYIVQEPZCPLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  异氰基乙酸乙酯 、 2-benzylidene-4-(4-nitrophenyl)-1-phenylbut-3-yn-1-one 在 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以51%的产率得到ethyl 4-benzoyl-8-nitro-3-phenyl-5H-indeno[1,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  异氰基乙酸酯的双亲核反应性：碱催化一锅法制备 4-氮杂芴和 4-氮杂芴酮

  摘要：

  为了快速合成 4-氮杂芴和 4-氮杂芴酮衍生物，开发了一种碱催化异氰基乙酸酯与各种烯炔酮的双环化。针对众所周知的 1,3-偶极反应性，异氰基乙酸酯的活性亚甲基和异氰基基团在这种多米诺骨牌转换中充当亲核试剂。

  DOI：

  10.1021/acs.orglett.1c03314

文献信息

• Tetrasubstituted Furans by Pd^II-Catalyzed Three-Component Domino Reactions of 2-(1-Alkynyl)-2-alken-1-ones with Nucleophiles and Vinyl Ketones or Acrolein
  作者：Renrong Liu、Junliang Zhang

  DOI：10.1002/chem.200901386

  日期：2009.9.21

  Multicomponent reaction: A novel PdII‐catalyzed three‐component cascade reaction of 2‐(1‐alkynyl)‐2‐alken‐1‐ones with nucleophiles and vinyl ketones has been developed (see scheme), which provides efficient, general, and atom‐economic access to tetrasubstituted, multifunctionalized furans.

  多组分反应：开发了一种新颖的Pd II催化的2-（1-炔基）-2-烯烃-1-酮与亲核试剂和乙烯基酮的三组分级联反应（请参见方案），该方法提供了高效，通用和高效的方法。原子经济途径获得四取代，多功能化的呋喃。
• An Unexpected Phosphine-Catalyzed Regio- and Diastereoselective [4+1] Annulation Reaction of Modified Allylic Compounds with Activated Enones
  作者：Zuliang Chen、Junliang Zhang

  DOI：10.1002/asia.201000193

  日期：——

  Rapid access: An unexpected regio‐ and diastereoselective phosphine‐catalyzed [4+1] annulation reaction of modified allylic compounds with activated enones was revealed, providing a simple, efficient route to synthesis of highly substituted 2,3‐dihydrofurans with convertible functional groups.

  快速访问：修饰的烯丙基化合物与活化的烯酮的意外的区域和非对映选择性膦催化的[4 + 1]环化反应被揭示，为合成具有可转换官能团的高度取代的2,3-二氢呋喃提供了一种简单有效的途径。
• Highly Functionalized 4-Alkylidenebicyclo[3.1.0]hex-2-enes by Tandem Michael Addition and Annulation of Electron-Deficient Enynes
  作者：Zuliang Chen、Junliang Zhang

  DOI：10.1002/asia.200900290

  日期：2009.10.5

  Rapid access: Highly functionalized 4‐alkylidenebicyclo[3.1.0]hex‐2‐enes can be rapidly constructed by a tandem Michael addition and formal [3+2] cycloaddition of electron deficient enynes with a crotonate‐derived sulfur ylide. The stereochemistry of all three newly formed carbon stereogenic centers and the double bond can be highly controlled in this domino process.

  快速访问：高度电子化的4-亚烷基双环[3.1.0] hex-2--enes可以通过将缺电子的炔烃与丁烯酸衍生的丁二酸内酯进行串联迈克尔加成反应和形式[3 + 2]环加成反应而快速构建。在该多米诺骨牌过程中，可以高度控制所有三个新形成的碳立体生成中心和双键的立体化学。
• Enantioselective synthesis of tetrasubstituted allenes via addition/arylation tandem reaction of 2-activated 1,3-enynes
  作者：Yongyan Zhang、Jin Wu、Lichao Ning、Qianping Chen、Xiaoming Feng、Xiaohua Liu

  DOI：10.1007/s11426-022-1443-5

  日期：2023.2

  We report the development of a new class of multifunctional chiral guanidine/Pd(0) catalyst system for 1,4-addition/arylation tandem reaction. A variety of tetra-substituted allenes were readily accessible from three-component “one-pot” transformations of acyclic or cyclic 2-activated 1,3-enynes, malonates and halobenzenes under mild reaction conditions. High levels of yield and enantioselectivity were achieved in the construction of stereogenic center and axis using readily available acyclic guanidine-amides. The mechanistic studies suggest that the guanidine/Pd(0) collaboration has obvious synergism to both base-dominated conjugate addition, and Pd(0)-dominated Heck-type reaction.

  我们报告了用于 1,4 加成/芳香化串联反应的新型多功能手性胍/钯（0）催化剂体系的开发情况。在温和的反应条件下，通过无环或环状 2-活化 1,3-烯炔、丙二酸盐和卤代苯的三组分 "一锅式 "转化，可以很容易地获得各种四取代烯烃。使用现成的无环胍酰胺构建立体中心和轴时，产量和对映体选择性都很高。机理研究表明，胍/钯（0）合作对碱基主导的共轭加成反应和钯（0）主导的赫克型反应都有明显的协同作用。
• Highly Regio- and Diastereoselective Synthesis of 6,7-Dihydro-4<i>H</i>-furo[3,4-<i>c</i>]pyran Derivatives through Pd-Catalyzed Formal (3 + 3) Allylic Cycloaddition of 2-Butene-1,4-diols with 2-(1-Alkynyl)-2-alken-1-ones
  作者：Tuanli Yao、Jun-E She、Tao Li、Xiangyang Qin

  DOI：10.1021/acs.orglett.4c00089

  日期：2024.3.15

  A highly efficient synthesis of 7-vinyl-6,7-dihydro-4H-furo[3,4-c]pyran derivatives from 2-butene-1,4-diols and 2-(1-alkynyl)-2-alken-1-ones has been achieved with high regio- and diastereoselectivity (dr > 20:1) by Pd-catalyzed tandem heterocyclization/cross-coupling. The π-allyl palladium species Int II generated from 2-butene-1,4-diol by direct cleavage of the C–OH bond is the key to the success

  由2-丁烯-1,4-二醇和2-(1-炔基)-2-烯烃高效合成7-乙烯基-6,7-二氢-4 H-呋喃[3,4 -c ]吡喃衍生物通过 Pd 催化的串联杂环化/交叉偶联，-1-酮已实现了高区域选择性和非对映选择性 (dr > 20:1)。通过直接裂解 C-OH 键由 2-丁烯-1,4-二醇生成的 π-烯丙基钯物种Int II是该正式 (3 + 3) 环加成反应成功的关键。