7-Methoxy-naphthoesaeure-(1)-methylester | 91903-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-Methoxy-naphthoesaeure-(1)-methylester
• 英文别名: Methyl 7-methoxynaphthalene-1-carboxylate；methyl 7-methoxynaphthalene-1-carboxylate
• CAS: 91903-17-2
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: XXXUZQMEPNHVAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  7-Methoxy-naphthoesaeure-(1)-methylester 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 7-甲氧基萘-1-羧醛
  参考文献：
  名称：

  Novel frameworks for trifluoromethyl ketone and phosphonate tsa inhibitors of type II PLA2

  摘要：

  Design and synthesis of some TSA inhibitors on novel molecular frameworks is described. This TSA analog design culminates in the preparation of the phosphonate 18. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00246-1
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 palladium diacetate 2,6-二叔丁基吡啶 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 7-Methoxy-naphthoesaeure-(1)-methylester
  参考文献：
  名称：

  Novel frameworks for trifluoromethyl ketone and phosphonate tsa inhibitors of type II PLA2

  摘要：

  Design and synthesis of some TSA inhibitors on novel molecular frameworks is described. This TSA analog design culminates in the preparation of the phosphonate 18. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00246-1

文献信息

• Metal-ammonia reduction and reductive alkylation of naphthalene sulphonamides. A new route to substituted naphthalenes.
  作者：L. Gottlieb、H.J.E. Loewenthal

  DOI：10.1016/s0040-4039(00)80526-2

  日期：1988.1

  Conditions have been found for the successful Birch reduction and reductive alkylation of N-alkyl arylsulphonamides, specifically in the naphthalene series. The derived C-alkylation products smoothly fragment on heating with re-aromatisation, affording a new specific route to 1-substituted naphthalenes starting from the 1-sulphonamides, and to both 2-mono-substituted and 2,4- (or 1,3-) disubstituted

  已经发现成功地使N-烷基芳基磺酰胺的Birch还原和还原性烷基化的条件，特别是在萘系列中。衍生的C-烷基化产物在加热后随着重新芳构化而平滑地断裂，从而提供了一条新的特定路线，从1-磺酰胺类化合物到1-取代的萘，再到2-单取代和2,4-（或1,3） -）来自相应的2-磺酰胺的二取代的萘。
• Metal-ammonia reduction and reductive alkylation of N-alkylnaphthalenesulfonamides. A new route to substituted naphthalenes
  作者：H. J. E. Loewenthal、L. Gottlieb

  DOI：10.1021/jo00035a018

  日期：1992.4

  Conditions have been found for 1,4-reduction of aromatic sulfonamides (conveniently monitored by electrical conductivity), using metals in THF/liquid ammonia on the pre-formed N-lithium salts (BuLi), without concomitant C-S reductive cleavage. The resulting 1,4-dihydro compounds could be alkylated, either in situ (in the case of simple unfunctionalized halides only) or, following isolation, after further N-alkylation and then forming the monoanion, or after forming the dianion of the N-monoalkylated dihydrosulfonamide, generally using as base n-butyllithium (a simple titration procedure). In the former case functionalized electrophiles (bromo esters, chloroformates) could be utilized. The ratio of alpha- to gamma-alkylation was dependent on the method of alkylation, the reaction medium, the nature of the N-alkyl group(s), and whether a monoanion or a dianion served as substrate. Gamma-Alkylation products could in some cases be further alpha-substituted. The alpha-substituted products aromatized, with loss of SO2 and amine, by heating, whereas gamma-substitution products required hydrolysis by aqueous alkali; this greatly facilitated separation where mixtures were formed. Thus, this dihydrosulfonamide route constitutes a novel and nucleophilic route to 1-substituted, 2-substituted, and, notably, 1,3-disubstituted naphthalenes.