2,3-dipropyl-1H-inden-1-one

• 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-dipropyl-1H-inden-1-one
• 英文别名: 2,3-dipropylinden-1-one
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: KJPDBAQXMQNITO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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 27.0h， 生成 2,3-dipropyl-1H-inden-1-one
  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

• Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of o-methoxycarbonylphenylboronic acid with alkynes
  作者：Mitsuhiro Ueda、Tamami Ueno、Yuki Suyama、Ilhyong Ryu

  DOI：10.1039/c6cc08032d

  日期：——

  Treatment of alkynes with o-methoxycarbonylphenylboronic acid in the presence of a cobalt catalyst resulted in the corresponding 2,3-disubstituted indenones.

  将炔烃与在钴催化剂存在下的o-甲氧羰基苯硼酸反应，得到相应的2,3-二取代的茚酮。
• Rhodium-catalyzed Carbonylative Annulation of 2-Bromobenzylic Alcohols with Internal Alkynes Using Furfural via β-Aryl Elimination
  作者：Takuma Furusawa、Hiroki Tanimoto、Yasuhiro Nishiyama、Tsumoru Morimoto、Kiyomi Kakiuchi

  DOI：10.1246/cl.170249

  日期：2017.7.5

  made in transformations of unstrained benzylic (tert-)alcohols through β-aryl elimination, catalytic carbonylation has not yet been developed extensively because alkoxycarbonylation is probably favored over β-aryl elimination. In this letter, we report on the rhodium(I)-catalyzed carbonylative annulation of α,α-dimethyl-(2-bromoaryl)methanols with internal alkynes using furfural leading to the formation

  尽管通过β-芳基消除在无应变的苄基（叔）醇转化方面取得了重大进展，但催化羰基化尚未得到广泛发展，因为烷氧基羰基化可能比β-芳基消除更受青睐。在这封信中，我们报告了铑（I）催化的α，α-二甲基-（2-溴芳基）甲醇与内部炔烃的羰基化环化，使用糠醛导致茚酮的形成。反应成功的关键是通过糠醛的脱羰及时产生羰基源。
• Palladium(II)-Catalyzed Annulation of Alkynes with <i>ortho</i>-Ester-Containing Phenylboronic Acids
  作者：Hirokazu Tsukamoto、Yoshinori Kondo

  DOI：10.1021/ol701776m

  日期：2007.10.1

  Palladium(II) catalyzes annulation of internal alkynes with methyl 2-boronobenzoate and (2-boronophenyl)acetate to provide 2,3-disubstituted indenones and 3,4-disubstituted 2-naphthols, respectively. The annulation reaction would proceed through transmetalation of Pd(II) with the boron reagents and insertion of the alkynes, followed by unprecedented 1,2-addition of the generated alkenylpalladium(II) species

  钯（II）催化2-炔基苯甲酸甲酯和（2-炔基苯基）乙酸甲酯的内部炔烃环化反应，分别提供2,3-二取代的茚满和3,4-二取代的2-萘酚。通过用硼试剂对Pd（II）进行重金属化并插入炔烃，然后将生成的烯基钯（II）物种进行前所未有的1,2-加成到分子内酯基中，环化反应将继续进行。
• Rhodium-catalyzed reaction of aroyl chlorides with alkynes or alkenes in the presence of disilanes
  作者：Ken Kokubo、Kenji Matsumasa、Masahiro Miura、Masakatsu Nomura

  DOI：10.1016/s0022-328x(98)00458-6

  日期：1998.6

  Internal alkynes effectively undergo aroylarylation, that is 1,2-addition of aroyl and aryl groups, on treatment with aroyl chlorides in the presence of a catalytic amount of [RhCl(cod)]2 and PPh3 using hexamethyldisilane as reducing agent to produce the corresponding 1,3-diaryl-2-propen-1-one derivatives in good yields. The reaction can also proceed using relatively reactive alkenes such as norbornenes

  内部炔烃在催化量的[RhCl（cod）] 2和PPh 3的存在下，使用六甲基乙硅烷作为还原剂，通过芳酰氯处理，可以有效地进行芳基芳基化反应，即芳基和芳基的1,2-加成反应。相应的1,3-二芳基-2-丙烯-1-酮衍生物，收率很高。该反应还可以使用相对反应性的烯烃例如降冰片烯代替炔烃进行。用芳酰氯对末端炔烃苯基乙炔进行类似的处理，引起芳酰基甲硅烷基化，得到1-芳基-2-苯基-3-三甲基甲硅烷基-2-丙烯-1-酮。
• 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。