6-acetyl-2,3-dihydro-1H-inden-1-one | 103987-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-acetyl-2,3-dihydro-1H-inden-1-one
• 英文别名: 6-acetylindanone；6-Acetyl-indanon-(1)；6-acetyl-indan-1-one；6-Acetyl-indan-1-on；6-Acetyl-2,3-dihydro-1H-inden-1-one；6-acetyl-2,3-dihydroinden-1-one
• CAS: 103987-99-1
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: NZRPETRDLFOTSC-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C(Solv: ligroine (8032-32-4))
• 沸点：
  346.4±31.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914399090

反应信息

• 作为反应物：
  描述：

  6-acetyl-2,3-dihydro-1H-inden-1-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 6-(α-Hydroxyethyl)-indanol-(1)
  参考文献：
  名称：

  Quere,J.-P.; Marechal,E., Bulletin de la Societe Chimique de France, 1971, p. 2227 - 2234

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯丙酸甲酯 在 sodium hydroxide 、 三氯化铝 、 sodium chloride 作用下， 以 二氯甲烷 为溶剂， 生成 6-acetyl-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Quere,J.-P.; Marechal,E., Bulletin de la Societe Chimique de France, 1971, p. 2227 - 2234

  摘要：

  DOI：

文献信息

• Two-Carbon Ring Expansion of 1-Indanones via Insertion of Ethylene into Carbon–Carbon Bonds
  作者：Ying Xia、Shusuke Ochi、Guangbin Dong

  DOI：10.1021/jacs.9b07445

  日期：2019.8.21

  A rhodium-catalyzed direct insertion of ethylene into a relatively unstrained carbon-carbon bond in 1-indanones is reported, which provides a two-carbon ring-expansion strategy for preparing seven-membered cyclic ketones. As many 1-indanones are commercially available and ethylene is inexpensive, this strategy simplifies synthesis of benzocycloheptenones that are valuable synthetic intermediates for

  据报道，铑催化乙烯直接插入 1-茚满酮中相对无应变的碳-碳键，为制备七元环酮提供了一种双碳扩环策略。由于许多 1-茚满酮可商购获得且乙烯价格低廉，因此该策略简化了苯并环庚烯酮的合成，苯环庚烯酮是生物活性化合物的宝贵合成中间体，但在其他方面制备具有挑战性。此外，该反应无副产物，氧化还原中性，并且可以耐受多种官能团，这可能对制备复杂环状分子的非常规战略键断开产生影响。
• Synthesis of benzo[c]fluorenone through a one-pot cascade reaction using inden-1-one derivatives
  作者：Shuyan Zheng、Hongsheng Tan、Xiaoguang Zhang、Chunhui Yu、Zhengwu Shen

  DOI：10.1016/j.tetlet.2013.11.081

  日期：2014.1

  A novel one-pot thermal cycloaddition of two indenones followed by a decarbonylation and dehydrogenation cascade afforded benzo[c]fluorenones regioselectively. Various substituted indenone derivatives were converted into their corresponding benzo[c]fluorenones in good to excellent yields.

  新颖的一锅法将两个茚满进行热环加成，然后进行脱羰和脱氢级联反应，从而选择性地提供了苯并[ c ]芴酮。各种取代的茚满酮衍生物均以良好或优异的产率转化为相应的苯并[ c ]芴酮。
• Intermolecular [5+2] Annulation between 1‐Indanones and Internal Alkynes by Rhodium‐Catalyzed C–C Activation
  作者：Rui Zhang、Ying Xia、Guangbin Dong

  DOI：10.1002/anie.202106007

  日期：2021.9.6

  Herein, we report a [5+2] cycloaddition between readily accessible 1-indanones and internal alkynes through Rh-catalyzed activation of less strained C−C bonds. The reaction is enabled by a strongly σ-donating NHC ligand and a carefully modified temporary directing group. A wide range of functional groups is tolerated, and the method provides straightforward access to diverse benzocycloheptenones that

  在此，我们报道了通过 Rh 催化的张力较小的 C−C 键活化，容易获得的 1-茚满酮和内部炔烃之间发生 [5+2] 环加成反应。该反应是通过强 σ 供体 NHC 配体和精心修饰的临时导向基团实现的。该方法可以耐受多种官能团，并且可以直接获得多种苯并环庚烯酮，而这些是其他方法难以获得的。反应机制的 DFT 研究表明迁移插入是周转限制步骤，并表明过渡态中有益的 π-π 相互作用。
• Rhodium complex-catalyzed desilylative cyclocarbonylation of 1-aryl-2-(trimethylsilyl)acetylenes: a new route to 2,3-dihydro-1H-inden-1-ones
  作者：Ryo Takeuchi、Hiroyuki Yasue

  DOI：10.1021/jo00072a020

  日期：1993.9

  Under water gas shift reaction conditions, 1-aryl-2-(trimethylsilyl)acetylenes undergo Rh-catalyzed desilylative cyclocarbonylation to give 2,3-dihydro-1H-inden-1-ones and trimethylsilanol. A wide variety of functional groups, such as methoxy, chloro, acetyl, ethoxycarbonyl, cyano, and trifluoromethyl, are tolerated on the aromatic ring under the reaction conditions. The products were obtained in good to excellent yield whether the substituent on the aromatic ring was electron-donating or electron-withdrawing. The cyclizations of substrates bearing a meta substituent on the aromatic ring regiospecifically gave 5-substituted-2,3-dihydro-1H-inden-1-ones except when the meta substituent was a methoxy group. The desilylative cyclocarbonylation is an alternative to the conventional preparation of 2,3-dihydro-1H-inden-1-ones, an intramolecular Friedel-Crafts acylation. A possible mechanism for the process is described.
• 890. Friedel–Crafts acylation and alkylation. A comparison of inter- and intra-molecular processes
  作者：G. Baddeley、R. Williamson

  DOI：10.1039/jr9560004647

  日期：——