2-{[4-(trifluoromethyl)phenyl]methylidene}-2,3-dihydro-1H-inden-1-one | 16307-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-{[4-(trifluoromethyl)phenyl]methylidene}-2,3-dihydro-1H-inden-1-one
• 英文别名: 2-[[4-(trifluoromethyl)phenyl]methylidene]-3H-inden-1-one
• CAS: 16307-11-2
• 化学式: C₁₇H₁₁F₃O
• mdl: MFCD03828965
• 分子量: 288.269
• InChiKey: PMOOCLYARYYYQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{[4-(trifluoromethyl)phenyl]methylidene}-2,3-dihydro-1H-inden-1-one 在 palladium on activated charcoal 氢气 作用下， 生成 N,N-diethyl-2-[2-[[4-(trifluoromethyl)phenyl]methyl]-3H-inden-1-yl]ethanamine
  参考文献：
  名称：

  影响中枢神经系统的化合物。IV。取代的2-苄基-3-二烷基氨基烷基茚和相关化合物。

  摘要：

  DOI：

  10.1021/jm00317a016
• 作为产物：
  描述：

  4-三氟甲基苯基溴化镁 生成 2-{[4-(trifluoromethyl)phenyl]methylidene}-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  影响中枢神经系统的化合物。IV。取代的2-苄基-3-二烷基氨基烷基茚和相关化合物。

  摘要：

  DOI：

  10.1021/jm00317a016

文献信息

• Iridium-catalyzed chemoselective transfer hydrogenation of α, β-unsaturated ketones to saturated ketones in water
  作者：Xiaolan Jiang、Xiaofeng Cui、Jinxun Chen、Qixing Liu、Yongsheng Chen、Haifeng Zhou

  DOI：10.1016/j.tetlet.2021.153627

  日期：2022.2

  A chemoselective iridium-catalyzed transfer hydrogenation of α, β-unsaturated ketones was realized in water. The CC double bonds of 2-benzylidene indanones and analogues were hydrogenated exclusively catalyzed by an iridium complex (0.1 mol%) bearing a pyridine-imidazoline ligand, using a mixture of formic acid/triethyl amine (molar ratio: 5/2) as a hydrogen source in water. A series of 2-benzyl indanones

  在水中实现了 α, β-不饱和酮的化学选择性铱催化转移氢化。使用甲酸/三乙胺（摩尔比：5/2）的混合物作为水中的氢源。获得了一系列2-苄基茚满酮及其类似物，具有良好的官能团耐受性和良好的收率。这种方法的实用性也通过克级合成得到证明。
• Construction of spirocycles containing highly substituted pyrroli-dine and 1-indanone motifs with spiro quaternary stereogenic centers via 1,3-dipolar cycloaddition of 2-alkylidene-1-indanone and azomethine ylides promoted by simple imidazolium salts
  作者：Wei-Qiang Hu、Yan-Su Cui、Zhi-Jun Wu、Chuan-Bao Zhang、Pei-Hao Dou、Song-Yang Niu、Ji-Ya Fu、Yong Liu

  DOI：10.1039/c5ra11536a

  日期：——

  The 1,3-dipolar cycloaddition of 2-alkylidene-1-indanone with azomethine ylides has been successfully developed promoted by simple imidazolium salts to construct a variety of spirocycles, containing highly substituted pyrrolidines, in excellent yields (up to 99%).

  2-烷基亚甲基-1-茚酮与偶氮甲基叶立德发生1,3-双极环加成反应，由简单的咪唑盐促进成功开发，构建了多种螺环化合物，其中含有高度取代的吡咯烷，产率极高（高达99%）。
• Electronically-controlled diastereoselective synthesis of spirocycles <i>via</i> [4 + 2] cycloaddition of 2-arylidene-1-indenones with benzyne
  作者：Subhasish Ray、Anup Kumar Yadav、Saurabh Singh、Monish Arbaz Ansari、Maya Shankar Singh

  DOI：10.1039/d3ob00417a

  日期：——

  A one-pot electronically controlled [4 + 2] cycloaddition reaction of in situ generated benzyne with 2-arylidene-1-indenone is unveiled to construct novel spirocyclic frameworks in a regio- and diastereoselective fashion. This protocol features operational simplicity, good functional group tolerance and avoids the use of metal catalysts and external additives. This methodology has extended the synthetic

  揭示了原位生成的苯与 2-亚芳基-1-茚酮的单锅电子控制 [4 + 2] 环加成反应，以区域和非对映选择性方式构建新型螺环框架。该协议具有操作简单、良好的官能团耐受性并避免使用金属催化剂和外部添加剂的特点。这种方法扩展了 2-arylidene-1-indenones 的合成应用，可以轻松获得有价值的 10' H -spiro[indene-2,9'-phenanthren]-1(3 H )-ones 并获得高产率。
• A regioselective [3 + 2] cycloaddition reaction of 2-benzylidene-1-indenones with functional olefins to access indanone-fused 2D/3D skeletons
  作者：Yi-Hang Deng、Chuan-Bao Zhang、Jun-Jie Sun、Wen-Li Xu、Ji-Ya Fu

  DOI：10.1039/d3ob00559c

  日期：——

  The regioselective [3 + 2] cycloaddition reaction of 2-benzylidene-1-indenones with functional olefins was established with DABCO as a base under mild conditions. Using this approach, a series of diversely substituted indanone-fused cyclopentane polycycles with highly crowded multiple substituents were synthesized in high yields.

  以DABCO为碱，在温和条件下建立了2-亚苄基-1-茚酮与功能烯烃的区域选择性[3 + 2]环加成反应。使用这种方法，以高产率合成了一系列具有高度拥挤的多个取代基的不同取代的茚满酮稠合环戊烷多环化合物。
• Intramolecular 1,2-Aroyl Migration in Spiro Donor–Acceptor Cyclopropanes: Formation of 1,4-Naphthoquinones and 1-Naphthols as Ring-Expansion Products
  作者：Franklin Leslin Daniel、Kannupal Srinivasan

  DOI：10.1021/acs.joc.3c02671

  日期：2024.4.19

  known rearrangement reactions of donor–acceptor cyclopropanes (DACs) involve the migration of cationic carbon atom to anionic carbon or heteroatoms in 1,3- or 1,4-positions. In the present work, we observed that spiro DACs based on 1,3-indanedione or 1-indanone moiety undergo intramolecular 1,2-aroyl migration when treated with titanium(IV) chloride to afford 1,4-naphthoquinones and α-naphthols readily

  大多数已知的供体-受体环丙烷（DAC）重排反应涉及阳离子碳原子向阴离子碳或1,3-或1,4-位杂原子的迁移。在目前的工作中，我们观察到基于 1,3-茚满二酮或 1-茚满酮部分的螺环 DAC 在用氯化钛（IV）处理时会发生分子内 1,2-芳酰基迁移，从而很容易地生成 1,4-萘醌和 α-萘酚。该反应通过形成推定的 1,3-偶极中间体，然后芳酰基裂解并迁移至相邻的碳以提供环扩展产物而发生。