1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop 2-yl methanesulfonate | 81112-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop 2-yl methanesulfonate
• 英文别名: 1,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate；[1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-yl] methanesulfonate
• CAS: 81112-05-2
• 化学式: C₁₇H₂₂O₆S
• 分子量: 354.424
• InChiKey: XFSFCYMBIFIDHI-UHFFFAOYSA-N

物化性质

• 沸点：
  519.5±50.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop 2-yl methanesulfonate 在 calcium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以94%的产率得到萘普生甲基酯
  参考文献：
  名称：

  利用芳基的1,2-重排合成α-芳基链烷酸的新方法

  摘要：

  一种简单的α-芳基链烷酸合成方法是通过使用芳基的新型1,2-重排完成的，并将该方法应用于某些生物学上重要的物质的合成。

  DOI：

  10.1016/s0040-4039(01)82941-5
• 作为产物：
  描述：

  6-甲氧基-2-丙酰萘 在 pyridinium hydrobromide perbromide 作用下， 以 1,4-二氧六环 为溶剂， 生成 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop 2-yl methanesulfonate
  参考文献：
  名称：

  利用芳基的1,2-重排合成α-芳基链烷酸的新方法

  摘要：

  一种简单的α-芳基链烷酸合成方法是通过使用芳基的新型1,2-重排完成的，并将该方法应用于某些生物学上重要的物质的合成。

  DOI：

  10.1016/s0040-4039(01)82941-5

文献信息

• Manufacture of alpha-arylalkanoic acids and precursors
  申请人：Syntex Pharmaceuticals International Limited

  公开号：US04542237A1

  公开（公告）日：1985-09-17

  .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.

  通过形成芳基烷基酮的α-羟基缩醛或硫缩醛，激活α-羟基取代基以形成相应的缩醛或硫缩醛酯底物，其中酯基足够不稳定，可以在带有质子或双极非质子溶剂中与底物非催化地解离，将酯底物与质子或双极非质子溶剂或其混合物接触足够的时间以形成相应的α-芳基烷酸或酯，缩醛或酰胺，可选择同时或顺序水解任何形成的酯，缩醛或酰胺以形成相应的α-芳基烷酸。
• Preparation of .alpha.-arylalkanoic acids
  申请人：Syntex Pharmaceutical International Limited

  公开号：US04912254A1

  公开（公告）日：1990-03-27

  Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.

  药用的光学活性α-芳基烷酸或酯、正酯或酰胺可通过将芳基镁格氏试剂与光学活性α-取代酰卤反应，形成光学活性芳基α-取代烷基酮，然后进行缩酮和重排，制备所需的光学活性α-芳基烷酸或相应的酯、正酯或酰胺。在另一种实施方案中，将芳基α-取代烷基酮还原为相应的醇，然后重排成α-芳基醛。所产生的醛通过常规方法转化为所需的光学活性α-芳基烷酸。
• Optically active alpha-naththylalkyl ketones
  申请人：Syntex Pharmaceuticals International Ltd.

  公开号：US05210258A1

  公开（公告）日：1993-05-11

  Optically active naphthyl alpha-substituted alkyl ketones, are a class of ketones useful as intermediates in the production of optically active alpha-naphthylalkanoic acids which exhibit anti-inflammatory, analgesic and anti-pyretic activity.

  具有光学活性的萘基α-取代烷基酮是一类有用的酮类中间体，可用于生产具有抗炎、镇痛和退热活性的光学活性α-萘基烷酸。
• Preparation of stereoisomers of ketals
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04749804A1

  公开（公告）日：1988-06-07

  Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.

  制备药用光学活性的α-芳基烷基酸或酯、ortho酯或其酰胺的方法是，将芳基镁Grignard试剂与光学活性的α-取代酰卤反应，形成光学活性的芳基α-取代烷基酮，然后进行缩酮和重排，以制备所需的光学活性α-芳基烷基酸或其相应的酯、ortho酯或酰胺。在另一种实施方案中，将芳基α-取代烷基酮还原为相应的脂肪醇，然后重排为α-芳基烷醛。所产生的烷醛通过常规方法转化为所需的光学活性α-芳基烷基酸。
• Process for preparing alpha-aromatic group substituted alkanoic acids or esters thereof
  申请人：SYNTEX PHARMACEUTICALS INTERNATIONAL LIMITED

  公开号：EP0048136A2

  公开（公告）日：1982-03-24

  A process for preparing an alpha-aromatic group substituted alkanoic acid or its ester of the general formula wherein Ar represents an aromatic group and R' represents a hydrogen atom or a saturated aliphatic group, or Ar and R1 may form a condensed ring together with the carbon atom to which they are bonded; and R2 represents a hydrogen atom, an alkyl group, or a hydroxyalkyl group. characterized in that an alpha-sulfonyloxyketone acetal of the general formula wherein R3 and R4, independently from each other, represent an alkyl group, or taken together, represent an alkylene group; R5 represents a substituted or unsubstituted alkyl group or an aromatic group; and Ar and R1 are as defined above, is hydrolyzed, or treated with an agent having affinity for oxygen: and novel intermediate compounds of the general formula (II) used in aforesaid process.

  一种通式为α-芳香族取代的烷酸或其酯的制备方法 其中 Ar 代表芳香族基团，R'代表氢原子或饱和脂肪族基团，或 Ar 和 R1 可与它们所键合的碳原子一起形成缩合环；R2 代表氢原子、烷基或羟烷基。 其特征在于通式的α-磺酰氧基酮缩醛 其中 R3 和 R4 独立地代表一个烷基，或合在一起代表一个亚烷基；R5 代表一个取代或未取代的烷基或芳香基；Ar 和 R1 如上所定义。