3,3,3-trifluoro-2-hydroxy-2-(1-naphthyl)propanoic acid | 502607-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,3,3-trifluoro-2-hydroxy-2-(1-naphthyl)propanoic acid
• 英文别名: 3,3,3-trifluoro-2-hydroxy-2-naphthalen-1-ylpropanoic acid
• CAS: 502607-27-4
• 化学式: C₁₃H₉F₃O₃
• 分子量: 270.208
• InChiKey: BKNJCNSPCRCXEO-UHFFFAOYSA-N

物化性质

• 沸点：
  436.4±45.0 °C(Predicted)
• 密度：
  1.482±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,3,3-trifluoro-2-hydroxy-2-(1-naphthyl)propanoic acid 在 Co(III) ortho-phenylene-bis(N'-methyloxamidate) 、 氧气 、 特戊醛 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到1-三氟甲酰基萘
  参考文献：
  名称：

  Catalytic aerobic oxidative decarboxylation of α-trifluoromethyl-α-hydroxy acids to trifluoromethyl ketones

  摘要：

  The oxidative decarboxylation of alpha-trifluoromethyl-alpha-hydroxy acids to trifluoromethyl ketones is carried out under mild catalytic aerobic conditions using a cobalt(Ill) complex in the presence of pivalaldehyde. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00947-x
• 作为产物：
  描述：

  1-溴代萘 在 氢氧化钾 、 1,1-二溴乙烷 、 碘 、 magnesium 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 3,3,3-trifluoro-2-hydroxy-2-(1-naphthyl)propanoic acid
  参考文献：
  名称：

  Catalytic aerobic oxidative decarboxylation of α-trifluoromethyl-α-hydroxy acids to trifluoromethyl ketones

  摘要：

  The oxidative decarboxylation of alpha-trifluoromethyl-alpha-hydroxy acids to trifluoromethyl ketones is carried out under mild catalytic aerobic conditions using a cobalt(Ill) complex in the presence of pivalaldehyde. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00947-x

文献信息

• (1-Naphthyl)(trifluoromethyl) <i>O</i>-Carboxy Anhydride as a Chiral Derivatizing Agent: Eclipsed Conformation Enforced by Hydrogen Bonding
  作者：Olivier Thillaye du Boullay、Aurélie Alba、Fatima Oukhatar、Blanca Martin-Vaca、Didier Bourissou

  DOI：10.1021/ol801930m

  日期：2008.10.16

  The preparation of the (1-naphthyl)(trifluoromethyl) O-carboxy-anhydride 1 and its use as a chiral derivatizing agent with several a-chiral primary amines are reported. The very large Delta delta(RS) values observed in H-1 NMR have been correlated with a marked preference of the corresponding alpha-hydroxy-am ides for the eclipsed conformation. In comparison, the related O-methylated amides are shown to adopt staggered conformations, which substantiates the critical role of intramolecular hydrogen bonding in maximizing the anisotropic effect.