1,2,3,4-Tetrahydro-2-methyl-3-phenylisoquinolin-1-one | 21868-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1,2,3,4-Tetrahydro-2-methyl-3-phenylisoquinolin-1-one
• 英文别名: 3-phenyl-2-methyl-3,4-dihydro-2H-isoquinolin-1-one；(+/-)-N-methyl-3-phenyltetrahydroisoquinolinone；3,4-Dihydro-2-methyl-3-phenylisocarbostyril；2-Methyl-3-phenyl-3,4-dihydro-isocarbostyril；2-methyl-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one；2-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolinone；2-methyl-3-phenyl-3,4-dihydroisoquinolin-1-one
• CAS: 21868-89-3
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: ZMUXLFZXEWLBRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  396.3±41.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4-Tetrahydro-2-methyl-3-phenylisoquinolin-1-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到2-methyl-3-phenyl-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  A Convenient Synthesis of 3-Aryl-2-Methyl-3,4-Dihydro-1(2H)-Isoquinolones and -1,2,3,4-Tetrahydroisoquinolines

  摘要：

  A new methodology for the synthesis of 3-aryl-2-methyl-3,4-dihydro-2H-isoquinolin-1-ones and 3-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines is reported.

  DOI：

  10.1080/00397910008086902
• 作为产物：
  描述：

  (3S*,4S*)-2-methyl-1-oxo-3-phenyl-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid 在 ammonium hydroxide 作用下， 反应 2.0h， 以71%的产率得到1,2,3,4-Tetrahydro-2-methyl-3-phenylisoquinolin-1-one
  参考文献：
  名称：

  Photodecarboxylation of Arylacetic Acids.

  摘要：

  当羧基位于仲碳或叔碳上时，芳基乙酸在用 254 纳米光照射其碱性水溶液时会发生脱羧反应，产量相当可观，而相应的游离酸则不会发生脱羧反应。除了简单的脱羧反应（A 型）外，在某些化合物中还观察到另外两种副反应，即氧化脱羧反应（B 型）和脱羧二聚反应（C 型），尤其是在使用波长大于 290 纳米的光源时。观察到角取代菲啶酮衍生物的高产脱羧反应表明，如果底物设计得当，上述光脱羧反应将是一种有用的合成工具。

  DOI：

  10.1248/cpb.40.2188

文献信息

• X-Ray Crystal Structure and Photo Chemistry of N-Methyl-N-(1-phenylvinyl)benzamide
  作者：Sujit Kumar Dehury

  DOI：10.1007/s10870-011-0108-5

  日期：2011.9

  5]-H shift to give isomerized product A. The minor photoproduct B is supposed to be formed via photocyclization process followed by a loss of proton and the tautomerized product undergoes oxidation for the revival of aromaticity.Graphical AbstractIn this paper, the crystal structure and photochemistry of N-methyl-N-(1-phenylvinyl)benzamide (I) is reported.

  N-甲基-N-(1-苯基乙烯基)苯甲酰胺 (I) 具有经验式 C16H15NO，在单斜空间群 P21/n 中结晶，晶胞参数 a = 8.9101(2) Å, b = 15.1416(4) Å , c = 9.7737(2) Å, α = 90°, β = 109.3320(10)°, γ = 90°, Z = 4。有趣的是，化合物（I）在光照射下发生光环化反应，得到两个环状内酰胺（ A 和 B) 低于 3100 Å。化合物(I)可以在两个等价邻位中的任一个位置环化。内酰胺 A 的形成机制可能涉及在光照射下的电环闭环反应，得到六元环状两性离子中间体。环质子通过 [1, 5]-H 位移重排，得到异构化产物 A。
• Condensation of Laterally Lithiated <i>o</i>-Methyl and <i>o</i>-Ethyl Benzamides with Imines Mediated by (−)-Sparteine. Enantioselective Synthesis of Tetrahydroisoquinolin-1-ones
  作者：Volker Derdau、Victor Snieckus

  DOI：10.1021/jo001369+

  日期：2001.3.1

  The first asymmetric synthesis of tetrahydroisoquinolin-1-ones using a (-)-sparteine-mediated lateral metalation-imine addition sequence to furnish 3-phenyl tetrahydroisoquinolinones 3a with enantioselectivities up to 81% ee is described (Scheme 4). For amide 7b, imine addition products 10 and 11 have been obtained with high diastereoselectivities (91-97% de) and enantioselectivities (91-98% ee) (Scheme 8).
• Ishibashi, Hiroyuki; Ohata, Kohei; Niihara, Michiyo, Journal of the Chemical Society. Perkin transactions I, 2000, vol. 4, p. 547 - 554
  作者：Ishibashi, Hiroyuki、Ohata, Kohei、Niihara, Michiyo、Sato, Tatsunori、Ikeda, Masazumi

  DOI：——

  日期：——
• Photodecarboxylation of Arylacetic Acids.
  作者：Kimiaki ISOBE、Kunihiko MOHRI、Jun-ichi TAGA、Yuki SASAKI、Yoshisuke TSUDA

  DOI：10.1248/cpb.40.2188

  日期：——

  Arylacetic acids, when the carboxyl group is at a secondary or tertiary carbon, are decarboxylated in considerable yields on irradiation of their aqueous alkaline solutions with 254 nm light, while the corresponding free acids are not decarboxylated. Together with the simple decarboxylation reaction (type A), two other side reactions, oxidative decarboxylation (type B) and decarboxylative dimerization (type C), were observed for some compounds, particularly when >290 nm light was used. The observation of high-yield decarboxylation of angularly substituted phenanthridone derivatives suggests that the above photodecarboxylation reaction would be a useful synthetic tool, if the substrate is appropriately designed.

  当羧基位于仲碳或叔碳上时，芳基乙酸在用 254 纳米光照射其碱性水溶液时会发生脱羧反应，产量相当可观，而相应的游离酸则不会发生脱羧反应。除了简单的脱羧反应（A 型）外，在某些化合物中还观察到另外两种副反应，即氧化脱羧反应（B 型）和脱羧二聚反应（C 型），尤其是在使用波长大于 290 纳米的光源时。观察到角取代菲啶酮衍生物的高产脱羧反应表明，如果底物设计得当，上述光脱羧反应将是一种有用的合成工具。
• A Convenient Synthesis of 3-Aryl-2-Methyl-3,4-Dihydro-1(2<i>H</i>)-Isoquinolones and -1,2,3,4-Tetrahydroisoquinolines
  作者：Axel Couture、Eric Deniau、Pierre Grandclaudon、Stéphane Lebrun

  DOI：10.1080/00397910008086902

  日期：2000.8

  A new methodology for the synthesis of 3-aryl-2-methyl-3,4-dihydro-2H-isoquinolin-1-ones and 3-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines is reported.