methyl 1-formyl-7-naphthoate | 136415-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1-formyl-7-naphthoate
• 英文别名: Methyl 8-formyl-2-naphthalenecarboxylate；methyl 8-formylnaphthalene-2-carboxylate
• CAS: 136415-65-1
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: JUPKDTZEYIMPTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-formyl-7-naphthoate 在 palladium on activated charcoal 盐酸 、 lithium methanolate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 methyl (8-formylethyl)-2-naphthoate
  参考文献：
  名称：

  Synthesis and Biological Activity of New 3-Hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) Synthase Inhibitors: 2-Oxetanones with a Side Chain Mimicking the Folded Structure of 1233A.

  摘要：

  为模拟1233A（1）的折叠侧链构象，该化合物是一种3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）合酶抑制剂，合成了侧链含有芳环的1233A类似物。其中2-恶坦酮部分保持不变。在1233A及其合成类似物中，反式-3-羟甲基-4-[2-(7-甲氧羰基-1-萘基)乙基]-2-恶坦酮（23）显示了最高的HMG-CoA合酶体外抑制活性。讨论了侧链上的构效关系。

  DOI：

  10.1248/cpb.42.512
• 作为产物：
  描述：

  对甲基苯磺酸-2-萘酯 在 2,4,6-三甲基吡啶 、 palladium diacetate 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydroxide 、 氢气 、 溴 、 铁粉 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 methyl 1-formyl-7-naphthoate
  参考文献：
  名称：

  Synthesis and binding behavior of a Zn(II)-porphyrin having calix[5]arene cap

  摘要：

  The synthesis and binding behavior of a Zn(II)-porphyrin having a calix[5]arene cap are presented. In order to synthesize such a bridged porphyrin, 5,15-bis(7-carboxy-1-naphthyl)-10,20-diphenylporphyrin having the syn arrangement of two naphthalene rings has been prepared. Amidation of the porphyrin and calix[5]arene having two amino functions and subsequent treatment of Zn(OAc)(2) gave a calix[5]arene capped Zn-porphyrin. Calix[5]arene-Zn-porphyrin was found to bind 4-methylpyridine much stronger than TPP-Zn. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01655-6

文献信息

• Novel frameworks for trifluoromethyl ketone and phosphonate tsa inhibitors of type II PLA2
  作者：Ravi S. Garigipati、George Seibel、Ruth J. Mayer、Brian Bolognese、Mark McCord、Lisa A. Marshall、Jerry L. Adams

  DOI：10.1016/s0960-894x(97)00246-1

  日期：1997.6

  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.
• Synthesis and Biological Activity of New 3-Hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) Synthase Inhibitors: 2-Oxetanones with a Side Chain Mimicking the Folded Structure of 1233A.
  作者：Hirokazu HASHIZUME、Hajime ITO、Kohji YAMADA、Hajime NAGASHIMA、Munefumi KANAO、Hiroshi TOMODA、Toshiaki SUNAZUKA、Hidetoshi KUMAGAI、Satoshi OMURA

  DOI：10.1248/cpb.42.512

  日期：——

  To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxetanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.

  为模拟1233A（1）的折叠侧链构象，该化合物是一种3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）合酶抑制剂，合成了侧链含有芳环的1233A类似物。其中2-恶坦酮部分保持不变。在1233A及其合成类似物中，反式-3-羟甲基-4-[2-(7-甲氧羰基-1-萘基)乙基]-2-恶坦酮（23）显示了最高的HMG-CoA合酶体外抑制活性。讨论了侧链上的构效关系。
• Synthesis and binding behavior of a Zn(II)-porphyrin having calix[5]arene cap
  作者：Hajime Iwamoto、Yoshiko Yukimasa、Yoshimasa Fukazawa

  DOI：10.1016/s0040-4039(02)01655-6

  日期：2002.11

  The synthesis and binding behavior of a Zn(II)-porphyrin having a calix[5]arene cap are presented. In order to synthesize such a bridged porphyrin, 5,15-bis(7-carboxy-1-naphthyl)-10,20-diphenylporphyrin having the syn arrangement of two naphthalene rings has been prepared. Amidation of the porphyrin and calix[5]arene having two amino functions and subsequent treatment of Zn(OAc)(2) gave a calix[5]arene capped Zn-porphyrin. Calix[5]arene-Zn-porphyrin was found to bind 4-methylpyridine much stronger than TPP-Zn. (C) 2002 Elsevier Science Ltd. All rights reserved.