4-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-butyric acid methyl ester | 7442-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-butyric acid methyl ester
• 英文别名: 4-(1-Oxo-1,2,3,4-tetrahydro-[2]naphthyl)-buttersaeure-methylester；γ-<1-Oxo-1.2.3.4-tetrahydro-naphthyl-(2)>-buttersaeure-methylester；1.2.3.4-Tetrahydro-1-oxo-naphthalin-2-buttersaeure-methylester；methyl 4-(1-oxo-3,4-dihydro-2H-naphthalen-2-yl)butanoate
• CAS: 7442-51-5
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: ZAGGZCGIHLOZTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-butyric acid methyl ester 生成 4-(2-Methyl-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-butyric acid
  参考文献：
  名称：

  NASIPURI D.; GHOSH S. K., INDIAN J. CHEM., 1976, B14, NO 11, 819-822

  摘要：

  DOI：
• 作为产物：
  描述：

  重氮甲烷 、 1,2,3,4-tetrahydro-1-oxo-2-naphthalenebutanoic acid 在 乙醚 作用下， 生成 4-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-butyric acid methyl ester
  参考文献：
  名称：

  Synthesis of 1-Keto-Δ^4a,10a-dodecahydrophenanthrene, cis-9-Methyl-1-decalone, and other Cyclic Ketones

  摘要：

  DOI：

  10.1021/ja01216a047

文献信息

• Acid-catalyzed cyclization of some condensed cyclohexenone and cyclohexanone aliphatic acids
  作者：H. J. E. Loewenthal、Ziva Neuwirth

  DOI：10.1021/jo01278a002

  日期：1967.3
• The Cp₂TiPh-Mediated Reductive Radical Cyclization of Cyanoketones and Related Reactions. Efficient Trapping of Ketyl Radicals by Cp₂TiPh-Coordinated Polar Multiple Bonds
  作者：Yoshihiko Yamamoto、Daisuke Matsumi、Reiko Hattori、Kenji Itoh

  DOI：10.1021/jo982492s

  日期：1999.4.1

  The reductive radical cyclization of cyanoketones was achieved using Cp2TiPh. The Ti(III) reagent was prepared by the sequential addition of i-PrMgCl and PhMgBr to commercial Cp2TiCl2 in this order and used effectively without isolation. The cyclization of the gamma- and delta-cyanoketones was performed in toluene at ambient temperature for several hours to give alpha-hydroxycyclopentanones and hexanones in moderate to good yields, respectively. The titanium reagent independently coordinates to both the carbonyl and cyano termini. As a result of lowering the LUMO of the cyano group upon coordination of the Ti(III) species, the irreversible cyclization successfully proceeds without formation of the unstable iminyl radical intermediate. The ester group can also be activated by the coordination of Cp2TiPh, and aromatic ketones with an ester group at the gamma position are cyclized to give the corresponding alpha-hydroxyketones.
• Ugi,I. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 641, p. 63 - 70
  作者：Ugi,I. et al.

  DOI：——

  日期：——