2-(2-methoxy-1-naphthyl)oxazoline | 94321-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-methoxy-1-naphthyl)oxazoline
• 英文别名: 1-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-2-naphthyl methyl ether；2-(2-methoxynaphthalen-1-yl)-4,4-dimethyl-5H-1,3-oxazole
• CAS: 94321-29-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: LPTAWCRECCXSAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  408.6±28.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-methoxy-1-naphthyl)oxazoline 在 sodium tetrahydroborate 、 草酸 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 为溶剂， 生成 2-phenyl-1-naphthaldehyde
  参考文献：
  名称：

  Regiospecific synthesis of polysubstituted naphthalenes via oxazoline-mediated nucleophilic aromatic substitutions and additions

  摘要：

  An efficient procedure for the selective functionalization of several positions of 2-methoxynaphthalene is described. Nucleophilic aromatic substitutions were carried out by displacing both a methoxy group and a neutral amine ortho to an oxazoline 6. 4-Substituted naphthalenes 8 were obtained from nucleophilic aromatic addition of an allyllithium species to a position para to the oxazoline 6. The resultant dihydronaphthalenes were converted to the fully aromatic systems 9 or alternatively substituted in the 2-position to form 10. Reductive cleavage of the oxazoline moities in 7 and 9 proceeded smoothly, producing the substituted naphthaldehydes 11.

  DOI：

  10.1021/ja00029a032
• 作为产物：
  描述：

  2-甲氧基-1-萘甲酸 在 氯化亚砜 、 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 9.0h， 生成 2-(2-methoxy-1-naphthyl)oxazoline
  参考文献：
  名称：

  Regiospecific synthesis of polysubstituted naphthalenes via oxazoline-mediated nucleophilic aromatic substitutions and additions

  摘要：

  An efficient procedure for the selective functionalization of several positions of 2-methoxynaphthalene is described. Nucleophilic aromatic substitutions were carried out by displacing both a methoxy group and a neutral amine ortho to an oxazoline 6. 4-Substituted naphthalenes 8 were obtained from nucleophilic aromatic addition of an allyllithium species to a position para to the oxazoline 6. The resultant dihydronaphthalenes were converted to the fully aromatic systems 9 or alternatively substituted in the 2-position to form 10. Reductive cleavage of the oxazoline moities in 7 and 9 proceeded smoothly, producing the substituted naphthaldehydes 11.

  DOI：

  10.1021/ja00029a032

文献信息

• Analogs of mevalonolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals
  申请人：SANDOZ AG

  公开号：EP0117228A1

  公开（公告）日：1984-08-29

  Compounds of formula wherein the two groups Ro together form a radical of formula wherein R2 is hydrogen, C1-4alkyl, C1-4alkoxy, (except t-butoxy), trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R3 is hydrogen, C1-alkyl, C1-3alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that not more than one of R2 and R3 is trifluoromethyl, not more than one of R2 and R3 is phenoxy, and not more that one of R2 and R3 is benzyloxy, R1 is hydrogen, C1-6alkyl, fluoro, chloro or benzyloxy, R4 is hydrogen, C1-4alkyl, C1-4alkoxy, (except t-butoxy), trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R5 is hydrogen, C1-3alkyl, C1-3alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R5a is hydrogen, C1-2alkyl, Cl.2alkoxy, fluoro or chloro, and with the provisos that not more than one of R4 and R5 is trifluoromethyl, not more than one of R4 and R5 is phenoxy and not more than one of R4 and R5 is benzyloxy, X is -(CH2)n-, wherein n is 0, 1, or 3 and both q's are 0 or one is 0 and the other is 1 Z is wherein R6 is hydrogen or C1 3alkyl, with the general proviso that -X-Z and the R4 bearing phenyl group are ortho to each other, in free acid form or in the form of a physiologically- hydrolysable and -acceptable ester or a δ lactone thereof or in salt form. The compounds possess pharmacological properties and are indicated for use as pharmaceuticals e.g. in inhibiting cholesterol biosynthesis or treating atherosclerosis.

  式化合物 其中两个基团 Ro 共同形成一个式基 其中 R2 是氢、C1-4烷基、C1-4烷氧基（叔丁氧基除外）、三氟甲基、氟、氯、苯氧基或苄氧基、 R3 是氢、C1-烷基、C1-3-烷氧基、三氟甲基、氟、氯、苯氧基或苄氧基，但 R2 和 R3 中不能有一个以上是三氟甲基，R2 和 R3 中不能有一个以上是苯氧基，R2 和 R3 中不能有一个以上是苄氧基、 R1 是氢、C1-6 烷基、氟、氯或苄氧基、 R4 是氢、C1-4烷基、C1-4烷氧基（叔丁氧基除外）、三氟甲基、氟、氯、苯氧基或苄氧基、 R5 是氢、C1-3烷基、C1-3烷氧基、三氟甲基、氟、氯、苯氧基或苄氧基、 R5a 是氢、C1-2烷基、Cl.2烷氧基、氟或氯，但条件是 R4 和 R5 中不超过一个是三氟甲基，R4 和 R5 中不超过一个是苯氧基，R4 和 R5 中不超过一个是苄氧基、 X 是-(CH2)n-、 其中 n 为 0、1 或 3，两个 q 均为 0 或一个为 0，另一个为 1 Z 是 其中 R6 是氢或 C1 3 烷基，但一般情况下，-X-Z 和含苯基的 R4 相互正交、 游离酸形式或生理上可水解和可接受的酯或其 δ 内酯形式或盐形式。这些化合物具有药理特性，可用作药物，如抑制胆固醇的生物合成或治疗动脉粥样硬化。
• A synthesis of various substituted naphthalenones by additions to naphthyloxazolines
  作者：A. I. Meyers、Thomas G. Gant

  DOI：10.1021/jo00041a030

  日期：1992.7

  A series of synthetic manipulations on the naphthalene nucleus, containing a 1-(2-oxazolinyl) moiety, is described. Nucleophilic additions afford both regio- and stereoselective products in the 1- and 4-positions. The latter is oxidatively transformed in the 4-keto system 4 which can undergo various substitutions as well as carbonyl transpositions.
• 3-NAPHTHYL-3-CARBOXYALKYLTHIO OR OXY SUBSTITUTED ALKANOIC ACID LEUKOTRIENE ANTAGONISTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0527175A1

  公开（公告）日：1993-02-17
• EP0527175A4
  申请人：——

  公开号：EP0527175A4

  公开（公告）日：1993-05-05
• [EN] MEVALONOLACTONE ANALOGS, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS
  申请人：——

  公开号：WO1984002903A1

  公开（公告）日：1984-08-02

  (EN) Compounds of formula (I), wherein the two groups Ro together form a radical of formula (II) or -(CH2)4-, wherein R2 is hydrogen, C1-4 alkyl, C1-4 alkoxy, (except t-butoxy), trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R3 is hydrogen, C1-3 alkyl, C1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that not more than one of R2 and R3 is trifluoromethyl, not more than one of R2 and R3 is phenoxy, and not more that one of R2 and R3 is benzyloxy, R1 is hydrogen, C1-6 alkyl, fluoro, chloro or benzyloxy, R4 is hydrogen, C1-4 alkyl, C1-4 alkoxy, (except t-butoxy), trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R5 is hydrogen, C1-3 alkyl, C1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R5a is hydrogen, C1-2 alkyl, C1-2 alkoxy, fluoro or chloro, and with the provisos that not more than one of R4 and R5 is trifluoromethyl, not more than one of R4 and R5 is phenoxy and not more than one of R4 and R5 is benzyloxy, is -(CH2)n-, formula (III), wherein n is 0, 1, 2 or 3 and both q"s are 0 or one is 0 and the other is 1, Z is formula (IV), wherein R6 is hydrogen or C1-3 alkyl, with the general proviso that -X-Z and the R4 bearing phenyl group are ortho to each other; in free acid form or in the form of a physiologically-hydrolysable and -acceptable ester of a delta lactone thereof or in salt form. The compounds possess pharmacological properties and are indicated for use as pharmaceuticals, e.g. in inhibiting cholesterol biosynthesis or treating atherosclerosis. (FR) Composés de formule (I) où les deux groupes Ro forment ensemble un radical de formule (II) ou -(CH2)4-, où R2 est un hydrogène, un alcoyle comportant entre 1 et 4 atomes de carbone, un alkoxy comportant entre 1 et 4 atomes de carbone (à l"exception d"un t-butoxy), un trifluorométhyle, un fluoro, un chloro, un phenoxy ou benzyloxy, R3 est un hydrogène, un alcoyle comportant entre 1 et 3 atomes de carbone, un alkoxy comportant entre 1 et 3 atomes de carbone, un trifluorométhyle, un fluoro, un chloro, un phénoxy ou un benzyloxy, à condition que pas plus d"un des groupes R2 et R3 soit un trifluorométhyle, que pas plus d"un des groupes R2 et R3 soit un phénoxy et que pas plus d"un des groupes R2 et R3 soit un benzyloxy, R1 est un hydrogène, un alcoyle comportant entre 1 et 6 atomes de carbone, un fluoro, un chloro ou un benzyloxy, R4 est un hydrogène, un alcoyle comportant entre 1 et 4 atomes de carbone,un alkoxy comportant entre 1 et 4 atomes de carbone (à l"exception du t-butoxy), un trifluorométhyle, un fluoro, un chloro, un phenoxy ou un benzyloxy, R5 est un hydrogène, un alcoyle comportant entre 1 et 3 atomes de carbone, un alkoxy comportant entre 1 et 3 atomes de carbone, un trifluorométhyle, un fluoro, un chloro, un phenoxy ou un benzyloxy, R5a est un hydrogène, un alcoyle comportant 1 ou 2 atomes de carbone, un alkoxy comportant 1 ou 2 atomes de carbone, un fluoro ou un chloro, à condition que pas plus qu"un des groupes R4 et R5 soit un trifulorométhyle, que pas plus qu"un des groupes R4 et R5 soit un phenoxy et que pas plus qu"un des groupes R4 et R5 soit un benzyloxy, X est -(CH2)n-, (III) où n vaut 0, 1, 2 ou 3 et les deux q valent 0, ou l"un vaut 0 et l"autre 1, Z est (IV), où R6 est un hydrogène ou un alcolye comportant entre 1 et 3 atomes de carbone, avec la condition générale que -X-Z et le groupe phényle portant R4 soient en position ortho l"un par rapport à l"autre; sous forme d"acide libre ou sous forme d"un ester physiologiquement hydrolysable et acceptable ou de sa delta lactone, ou sous forme de sel. Ces composés possèdent des propriétés pharmacologiques et sont indiqués pour une utilisation en tant que produits pharmaceutiques, par exemple pour l"inhibition de la biosynthèse du cholestérol ou le traitement de l"athérosclérose.