2,3-diethyl-1H-inden-1-one | 75421-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2,3-diethyl-1H-inden-1-one
• 英文别名: 2,3-Diethylindenone；2,3-Diaethyl-indenon；2,3-Diethyl-inden-1-one；2,3-diethylinden-1-one
• CAS: 75421-58-8
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: BUDCKSLJPQKXET-UHFFFAOYSA-N

物化性质

• 沸点：
  303.1±25.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-己炔 、 邻溴苯甲酸甲酯 在 1,2-双(二苯基膦)乙烷氯化镍 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以73%的产率得到2,3-diethyl-1H-inden-1-one
  参考文献：
  名称：

  Ni-Catalyzed Larock Indenone Annulation with Aliphatic- and Silyl-Substituted Alkynes Supported by Mechanistic Analysis

  摘要：

  DOI：

  10.1021/acs.organomet.2c00016

文献信息

• An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water
  作者：Karu Ramesh、Gedu Satyanarayana

  DOI：10.1002/ejoc.201800591

  日期：2018.8.15

  A one‐pot synthesis of indenones, was presented. The reaction involved palladium catalyzed annulation of ortho‐halobenzaldehydes with internal alkynes. Notably, this process was successful in water as the sole green solvent. Significantly, unlike earlier reports, this protocol showed excellent regioselectivity with unsymmetrical alkylarylacetylenes. Further, the strategy was extended to a one‐pot synthesis

  介绍了茚酮的一锅法合成。该反应涉及钯催化的邻卤苯甲醛与内部炔烃的环化。值得注意的是，这个过程在水作为唯一的绿色溶剂中是成功的。值得注意的是，与之前的报道不同，该方案对不对称的烷基芳基乙炔表现出出色的区域选择性。此外，该策略扩展到新木脂素的一锅合成。
• Rhodium-Catalyzed Reaction of Aroyl Chlorides with Alkynes
  作者：Ken Kokubo、Kenji Matsumasa、Masahiro Miura、Masakatsu Nomura

  DOI：10.1021/jo960915p

  日期：1996.1.1

  involve chlororhodation to the alkynes by the intermediary arylchlororhodium(III) species generated in situ followed by reductive elimination of the products, which are suggested by the results of some control experiments. In contrast to the reaction with terminal alkynes, that with some internal ones proceeds without decarbonylation to produce 2,3-disubstituted-1-indenones as the predominant products.

  在催化量的[RhCl（cod）]（2）和PPh（3）的存在下，芳酰氯与末端炔烃反应并伴随脱羰作用，从而以良好的产率选择性和立体选择性地生成相应的氯乙烯衍生物。催化剂效率是PPh（3）与铑种类之比的显着函数。通过使用1.0的PPh（3）/ Rh比可获得令人满意的结果。该反应可能涉及通过现场生成的中间芳基氯铑（III）物种进行氯铑酰化成炔基，然后通过还原消除产物，这是一些对照实验的结果表明。与与末端炔烃的反应相反，在不脱羰的情况下进行一些内部炔烃反应，生成2,3-二取代-1-茚满作为主要产物。
• The Preparation and Evaluation of Electron Poor Benzylidene Fischer Carbene Complexes: Studies Toward the Total Synthesis of (+)-Olivin
  作者：Vincent P. Liptak、William D. Wulff

  DOI：10.1016/s0040-4020(00)00867-x

  日期：2000.12

  the benzannulation reaction is put forth using the electronic nature of substituents on the aryl ring of benzylidene Fischer carbene complexes as a handle to predict, using σ-para values as a guide, the outcome of the reaction based on the accepted mechanism. The design of this work focuses on evaluation of the synthetic utility of the benzannulation reaction and the means by which this reaction may

  的持续探入苯并环化反应的命运提出使用亚苄基费卡宾配合物的芳基环上的取代基的电子性质作为手柄来预测，使用σ -对位值作为指导，根据公认的机理得出反应的结果。这项工作的设计重点是评估苯环化反应的合成效用，以及改进该反应以使其成为制备复杂天然产物的较好合成工具的方法，这在我们正在进行的（ +）-olivin，它使用苯环化反应作为关键的收敛合成步骤。为了完成这些任务，进行了几种贫电子的亚苄基菲舍尔卡宾配合物的制备，并研究了它们与简单炔烃底物的反应。尽管关于富电子的亚苄基菲歇尔卡宾配合物的制备知之甚少，但对于其电子贫乏的对应物的制备却知之甚少。因此，也已经研究了开发这些难以捉摸的靶标的有用的制备方法的努力。尽管已经探索了使用基于碳和氧的芳基取代基，但是迄今为止，由于这些体系具有更直接的合成重要性，因此更大程度地开发了包含基于氧的芳基取代基的亚苄基卡宾配合物的制备。之所以如此，是因为已经被苄环化反应靶
• Substrate regulation of product distribution in the reactions of arylchromium carbene complexes with alkynes
  作者：Mary Ellen Bos、William D. Wulff、Ross A. Miller、Steven Chamberlin、Timothy A. Brandvold

  DOI：10.1021/ja00024a040

  日期：1991.11

  The reactions of arylcarbene complexes with alkynes were examined for six of the nine possible substitution patterns for mono- and dioxygenated aryl substituents of the carbene carbon. The product distributions were found to be highly dependent on a number of factors, including solvent, temperature, concentration of alkyne, and the nature of the aryl substituent. The product distributions were determined in nearly all cases for phenol and indene products and in some cases for furans, cyclobutenones, and cyclopentenediones, which were minor products in these reactions. The product distribution for the reaction of each arylcarbene complex was determined as a function of both temperature and alkyne concentration, since the combined product distribution profiles provided a much more sensitive measure of the relative influences of the aryl substituents on the reaction outcome. Furthermore, this distribution profile was determined for the reactions with 3-hexyne and I-pentyne for each carbene complex. A series of monosubstituted arylcarbene complexes were examined to identify the effects of oxygen substituents at various positions on the aryl ring. The m-methoxy group has no effect on the product distribution, whereas the o-methoxy group influences the distribution by its ability to chelate to the metal center and the p-methoxy group influences the distribution by its ability to donate electrons by resonance. The product distributions from the reactions of the 2,3-, 2,4-, and 2,5-dimethoxy complexes followed the profile expected from the simple sum of the profiles of the monomethoxyl complexes. In all cases where an effect was observed, higher concentrations of alkyne led to a higher selectivity for phenol over indene products. The dependence of the product distribution on the concentration of the alkyne substrate is suggested to be due to a process in which a second molecule of alkyne coordinates to the metal center and determines the chemical outcome of an intermediate that has covalently incorporated the first alkyne. It is further suggested that the special ability of an alkyne to display this effect is related to the ability of an alkyne to readily switch from a 2 to a 4 e- donor. This phenomenon of substrate regulation of product distribution is termed the allochemical effect, and a mechanistic explanation is developed that features this proposed process and that is refined to accommodate the observed effects of solvent, temperature, chelation, and steric and electronic effects that have been observed for the reaction of carbene complexes and alkynes.
• Martens,H.; Hoornaert,G., Synthetic Communications, 1972, vol. 2, p. 147 - 156
  作者：Martens,H.、Hoornaert,G.

  DOI：——

  日期：——