1-oxo-1,2,3,4-tetrahydro-arcidine | 85796-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-oxo-1,2,3,4-tetrahydro-arcidine
• 英文别名: 1,2,3,4,9,10-Hexahydro-1-acridone；3,4,9,10-tetrahydro-2H-acridin-1-one
• CAS: 85796-92-5
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: IGHFNLCNLTUOLU-UHFFFAOYSA-N

物化性质

• 沸点：
  367.1±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxo-1,2,3,4-tetrahydro-arcidine 在 对苯醌 作用下， 以100%的产率得到3,4-dihydroacridin-1(2H)-one
  参考文献：
  名称：

  One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines

  摘要：

  The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.

  DOI：

  10.1055/s-0033-1339922
• 作为产物：
  描述：

  2-(2-Bromobenzyl)-1,3-cyclohexanedione 在 N-甲基吡咯烷酮 、 四(三苯基膦)钯 、 <3THF*Mg2Cl2O*TiNCO> 作用下， 反应 12.0h， 以75%的产率得到1-oxo-1,2,3,4-tetrahydro-arcidine
  参考文献：
  名称：

  New C–N–C bond formation reaction using the nitrogenation-transmetallation process

  摘要：

  酮与芳基或乙烯基卤化物在钛异氰酸酯络合物[3THF·Mg2Cl2O·TiNCO]1和钯催化剂的存在下发生偶联反应，生成二乙烯基或芳基乙烯基胺，过程通过钛亚胺络合物6与芳基或乙烯基钯溴化物的金属间转移实现（THF为四氢呋喃）。

  DOI：

  10.1039/c39910000081

文献信息

• New C–N–C bond formation reaction using the nitrogenation-transmetallation process
  作者：Yasuhiro Uozumi、Miwako Mori、Masakatau Shibasaki

  DOI：10.1039/c39910000081

  日期：——

  Ketones and aryl or vinyl halides couple to give divinyl or arylvinyl amines in the presence of the titanium isocyanate complex [3THF·Mg2Cl2O·TiNCO]1 and a palladium catalyst, via transmetallation of the titano imine complex 6 with aryl or vinyl palladium bromide (THF tetrahydrofuran).

  酮与芳基或乙烯基卤化物在钛异氰酸酯络合物[3THF·Mg2Cl2O·TiNCO]1和钯催化剂的存在下发生偶联反应，生成二乙烯基或芳基乙烯基胺，过程通过钛亚胺络合物6与芳基或乙烯基钯溴化物的金属间转移实现（THF为四氢呋喃）。
• Generation and reactions of azaxylylenes
  作者：R.D. Bowen、D.E. Davies、C.W.G. Fishwick、T.O. Glasbey、S.J. Noyce、R.C. Storr

  DOI：10.1016/s0040-4039(00)85638-5

  日期：1982.1
• UOZUMI, YASUHIRO;MORI, MIWAKO;SHIBASAKI, MASAKATAU, J. CHEM. SOC. CHEM. COMMUN.,(1991) N, C. 81-83
  作者：UOZUMI, YASUHIRO、MORI, MIWAKO、SHIBASAKI, MASAKATAU

  DOI：——

  日期：——
• One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines
  作者：Julia Stephanidou-Stephanatou、Constantinos Tsoleridis、Constantinos Neochoritis、Nicolaos Eleftheriadis、Arianna Tsiantou

  DOI：10.1055/s-0033-1339922

  日期：——

  The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.
• New C-N-C Bond Formation Reaction Using Nitrogenation-Transmetallation Process. Novel Ring Construction of Indole and Quinoline Derivatives
  作者：Miwako Mori、Yasuhiro Uozumi、Masakatsu Shibasaki

  DOI：10.3987/com-91-s88

  日期：——

  Ketones and aryl or vinyl halides couple to give divinyl- or arylvinylamines in the presence of the titanium-isocyanate complex [3 THF.Mg2Cl2O.TiNCO] (1) and a palladium catalyst, via transmetallation of the titano imine complex (3) with aryl- or vinylpalladium bromide.