2-tert-Butyl-3-(tert-butylethyl)-1-indenone | 150192-46-4

• 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-tert-Butyl-3-(tert-butylethyl)-1-indenone
• 英文别名: 2-tert-butyl-3-(tert-butylethynyl)-1-indenone；2-tert-Butyl-3-(3,3-dimethylbut-1-yn-1-yl)-1H-inden-1-one；2-tert-butyl-3-(3,3-dimethylbut-1-ynyl)inden-1-one
• CAS: 150192-46-4
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: LCDGPDJEMZCZIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.5±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2-碘苄醇 在 palladium diacetate 四丁基氯化铵 、 sodium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 48.0h， 生成 2-tert-Butyl-3-(tert-butylethyl)-1-indenone
  参考文献：
  名称：

  Synthesis of indenones via palladium-catalyzed annulation of internal alkynes

  摘要：

  A number of 2,3-disubstituted 1-indenones have been prepared in fair to good yields by treating o-iodo- or o-bromobenzaldehyde with various internal alkynes in the presence of a palladium catalyst. Synthetically, the methodology provides an especially convenient route to stable hindered indenones containing aryl, silyl, and tert-alkyl groups. The reaction is believed to proceed through a palladium-(IV) intermediate, and the regiochemistry of the reaction is controlled sterically.

  DOI：

  10.1021/jo00069a017

文献信息

• Carbopalladation of Nitriles:  Synthesis of 2,3-Diarylindenones and Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulation of Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles
  作者：Alexandre A. Pletnev、Qingping Tian、Richard C. Larock

  DOI：10.1021/jo026178g

  日期：2002.12.1

  represents one of the first examples of the addition of an organopalladium moiety to the carbon-nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.

  2-碘苄腈，其衍生物和各种杂环类似物在二芳基乙炔或双环烯烃上进行钯（0）催化的环化反应，从而以非常好的至极好的收率得到2,3-二芳基萘和多环芳族酮。该反应代表将有机钯部分加成到腈的碳-氮三键上的第一个例子。该反应与许多官能团相容。提出了反应机理以及考虑取代基对腈芳环电子效应的模型。
• Rh(I)-Catalyzed Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Leading to Indenones
  作者：Yasuyuki Harada、Jun Nakanishi、Hirokazu Fujihara、Mamoru Tobisu、Yoshiya Fukumoto、Naoto Chatani

  DOI：10.1021/ja070107n

  日期：2007.5.1

  reaction of alkynes with 2-bromophenylboronic acids under nitrogen gives naphthalene derivatives, in which two molecules of alkynes are incorporated. A vinylrhodium complex similar to II can also be generated by a different route by employing 2-bromophenyl(trimethylsilyl)acetylene and arylboronic acids in the presence of Rh(I) complex as the catalyst, resulting in the formation of indenones. The reaction

  炔烃与 2-溴苯基硼酸的 Rh 催化反应涉及羰基化环化以得到茚酮。该反应的关键步骤包括将芳基铑 (I) 物质加成到炔烃上，并在相邻的苯环上氧化加成 C-Br 键，得到乙烯基铑 (I) 物质 II。区域选择性取决于炔烃上取代基的电子和空间性质。庞大的基团和吸电子基团有利于茚酮的 - 位置。在甲硅烷基或酯取代的炔烃的情况下，区域选择性非常高。选择性按照 SiMe3 > COOR >> 芳基 >> 烷基的顺序增加。降冰片烯与 2-溴苯基硼酸在 1 个大气压的 CO 下反应得到相应的茚满酮衍生物。炔烃与 2-溴苯基硼酸在氮气下反应生成萘衍生物，其中结合了两分子炔烃。在Rh(I)配合物的存在下，使用2-溴苯基(三甲基甲硅烷基)乙炔和芳基硼酸作为催化剂，从而形成茚酮，也可以通过不同的途径生成类似于II的乙烯基铑配合物。1-(2-溴苯基)-hept-2-yn-1-one 与 PhB(OH)2 在 Rh(I)
• Rhodium-Catalyzed Annulation Reactions of 2-Cyanophenylboronic Acid with Alkynes and Strained Alkenes
  作者：Tomoya Miura、Masahiro Murakami

  DOI：10.1021/ol051249u

  日期：2005.7.1

  A new [3 + 2] annulation reaction was developed in which 2-cyanophenylboronic acid reacted as a three-carbon component with alkynes or alkenes to afford substituted indenones or indanones. The use of an alkynoate even produced benzotropone, a formal [3 + 2 + 2] adduct. The cyclic skeletons were constructed by intramolecular nucleophilic addition of an intermediate organorhodium(I) species to a cyano group.
• Synthesis of indenones via palladium-catalyzed annulation of internal alkynes
  作者：R. C. Larock、M. J. Doty、S. Cacchi

  DOI：10.1021/jo00069a017

  日期：1993.8

  A number of 2,3-disubstituted 1-indenones have been prepared in fair to good yields by treating o-iodo- or o-bromobenzaldehyde with various internal alkynes in the presence of a palladium catalyst. Synthetically, the methodology provides an especially convenient route to stable hindered indenones containing aryl, silyl, and tert-alkyl groups. The reaction is believed to proceed through a palladium-(IV) intermediate, and the regiochemistry of the reaction is controlled sterically.