4-(2-naphthyl)pentanoic acid | 87014-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-naphthyl)pentanoic acid
• 英文别名: β-(γ-Methyl)-buttersaeurenaphthyl；4-[2]naphthyl-valeric acid；4-[2]Naphthyl-valeriansaeure；4-naphthalen-2-ylpentanoic acid
• CAS: 87014-93-5
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: JMERSRXFEAUEHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-naphthyl)pentanoic acid 在 甲烷磺酸 作用下， 反应 1.0h， 以43%的产率得到1-methyl-1,2,3,4-tetrahydro-4-phenanthrone
  参考文献：
  名称：

  Conformational effects on the enantioselective recognition of 4-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene derivatives by a Naproxen-derived chiral stationary phase

  摘要：

  4-(3,5-Dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene and derivatives having methyl groups in various positions on the tetrahydro ring were synthesized and resolved on an (S)-Naproxen-derived chiral stationary phase. The difference in the Gibbs free energy, DeltaDeltaG, of the transient diastereomeric adsorbates was determined from the chromatographic data. The highest enantioselectivity was observed for cis-4-(3,5-dinitrobenzamido)-3-methyl-1,2,3,4-tetrahydrophenanthrene. Introducing methyl groups into other positions of the tetrahydrophenanthrene ring proved to be detrimental to enantioselectivity. Prior studies indicate that, in the 4-(3,5-dinitrobenzamido)1,2,3,4-tetrahydrophenanthrene used in the Whelk-O chiral HPLC columns, the 3,5-dinitrobenzamide group occupies a pseudoaxial position, thus forming one wall of a binding cleft owing to its spatial relationship with the naphthyl portion of the selector. The effect of the methyl substituents on enantioselectivity is attributed to their ability to both influence the 'psuedoaxiality' of the dinitrobenzamido group and to their ability to sterically hinder the presentation of the 'back face' of this group to the Naproxen-derived selector. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00307-1
• 作为产物：
  描述：

  (E)-4-(naphthalen-2-yl)pent-3-enoic acid 在 氢氧化钾 、 镍 作用下， 生成 4-(2-naphthyl)pentanoic acid
  参考文献：
  名称：

  Colonge; Domenech, Bulletin de la Societe Chimique de France, 1952, p. 634,637

  摘要：

  DOI：

文献信息

• REACTIONS OF 1,2,3,4-TETRAHYDROPHENANTHRENE AND DERIVATIVES. VI. COMPOUNDS DERIVED FROM 1-METHYLTETRAHYDROPHENANTHRENE
  作者：W. E. BACHMANN、R. F. EDGERTON

  DOI：10.1021/jo01151a032

  日期：1950.9
• Johnson; Johnson; Petersen, Journal of the American Chemical Society, 1945, vol. 67, p. 1360,1364
  作者：Johnson、Johnson、Petersen

  DOI：——

  日期：——