rac-萘普生2-丙基酯 | 68641-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: rac-萘普生2-丙基酯
• 英文名称: (+/-)-6-methoxy-α-methyl-2-naphthaleneacetic acid isopropyl ester
• 英文别名: Isopropyl 2-(2-methoxynaphthalen-6-yl)propanoate；propan-2-yl 2-(6-methoxynaphthalen-2-yl)propanoate
• CAS: 68641-85-0
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: KABDXMXJNHRMMO-UHFFFAOYSA-N

物化性质

• 熔点：
  40 - 43°C
• 沸点：
  381.2±17.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-萘普生2-丙基酯 在 chiral-plannar ferrocenyl derivative 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 2-(6-methoxy-naphthalen-2-yl)-2-methyl-3-oxo-butyric acid isopropyl ester
  参考文献：
  名称：

  Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters:  Synthetic and Mechanistic Studies of the C-Acylation of Silyl Ketene Acetals

  摘要：

  With the aid of an appropriate chiral catalyst, acyclic silyl ketene acetals react with anhydrides to furnish 1,3-dicarbonyl compounds that bear all-carbon quaternary stereocenters in good ee and yield. Mechanistic studies provide strong support for a catalytic cycle that involves activation of both the electrophile (anhydride -> acylpyridinium) and the nucleophile (silyl ketene acetal -> enolate).

  DOI：

  10.1021/ja043832w
• 作为产物：
  描述：

  2-(6-甲氧基-2-萘基)丙酸 、 异丙醇 在 硫酸 作用下， 反应 12.0h， 以69%的产率得到rac-萘普生2-丙基酯
  参考文献：
  名称：

  （S）萘普生不对称合成中前手性烯醇的对映选择性质子化。

  摘要：

  外消旋的甲基，异-丙基和叔-丁基酯萘普生衍生物用非手性碱LDA，得到相应的烯醇化物的前手性处理2 -Li，3 -Li和4 -Li。这些具有新的手性质子源（S）-10和（S，S）-11的含α-苯基乙基氨基基团的烯醇化子以高度对映选择性的方式进行。对映体富集的酯衍生物的皂化2 - 4得到萘普生，（小号） - 1，没有对映体纯度的损耗。

  DOI：

  10.1016/s0040-4039(03)00217-x

文献信息

• Enzymatic resolution of naproxen
  作者：Surrinder Koul、Rajinder Parshad、Subhash C. Taneja、Ghulam N. Qazi

  DOI：10.1016/s0957-4166(03)00492-0

  日期：2003.8

  Trichosporon sp. (TSL), a newly found strain isolated from a locally fermented cottage cheese has been found to be highly stereoselective in the resolution of (S)-(+)-naproxen (ee >99%, Esimilar to500) from the corresponding racemic methyl ester. The process of resolution using whole cells has been scaled up to multi-kg level. Optimization of experimental conditions including downstream processing at 80-100 g/L substrate concentration with >90% recovery has been achieved. Changes in the physical parameters such as the particle size of the substrate play an important role in the resolution kinetics. A new strain of Trichosporon sp. having high cell density in cultivation (>60 g dry cell mass L-1 in 14-16 h) is found to be sufficiently stable for two years in dry powder form at 5-8degreesC. The viability of the resolution process has been further improved by the development of a simple racemization process for the enriched (R)-(-)-ester. (C) 2003 Elsevier Ltd. All rights reserved.
• Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters:  Synthetic and Mechanistic Studies of the C-Acylation of Silyl Ketene Acetals
  作者：Ara H. Mermerian、Gregory C. Fu

  DOI：10.1021/ja043832w

  日期：2005.4.1

  With the aid of an appropriate chiral catalyst, acyclic silyl ketene acetals react with anhydrides to furnish 1,3-dicarbonyl compounds that bear all-carbon quaternary stereocenters in good ee and yield. Mechanistic studies provide strong support for a catalytic cycle that involves activation of both the electrophile (anhydride -> acylpyridinium) and the nucleophile (silyl ketene acetal -> enolate).
• Enantioselective protonation of prochiral enolates in the asymmetric synthesis of (S)-naproxen
  作者：Omar Muñoz-Muñiz、Eusebio Juaristi

  DOI：10.1016/s0040-4039(03)00217-x

  日期：2003.3

  tert-butyl ester derivatives of naproxen were treated with achiral LDA base to give the corresponding prochiral enolates 2-Li, 3-Li, and 4-Li. Protonation of these enolates with novel chiral proton sources (S)-10 and (S,S)-11, containing the α-phenylethylamino group, proceeded in a highly enantioselective manner. Saponification of enantioenriched ester derivatives 2–4 afforded naproxen, (S)-1, with no loss

  外消旋的甲基，异-丙基和叔-丁基酯萘普生衍生物用非手性碱LDA，得到相应的烯醇化物的前手性处理2 -Li，3 -Li和4 -Li。这些具有新的手性质子源（S）-10和（S，S）-11的含α-苯基乙基氨基基团的烯醇化子以高度对映选择性的方式进行。对映体富集的酯衍生物的皂化2 - 4得到萘普生，（小号） - 1，没有对映体纯度的损耗。