ethyl 2,3-dimethoxynaphthalene-6-carboxylate | 82590-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2,3-dimethoxynaphthalene-6-carboxylate
• 英文别名: 6,7-dimethoxy-2-naphthoic acid ethyl ester；Ethyl 6,7-dimethoxy-2-naphthoate；ethyl 6,7-methoxy-2-naphthoate；6,7-dimethoxy-[2]naphthoic acid ethyl ester；6,7-Dimethoxy-[2]naphthoesaeure-aethylester；ethyl 2,3-dimethoxynaphthalen-6-carboxylate；Ethyl 6,7-dimethoxynaphthalene-2-carboxylate
• CAS: 82590-34-9
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: ONTZGHVJHIVWRD-UHFFFAOYSA-N

物化性质

• 熔点：
  109 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  381.0±22.0 °C(Predicted)
• 密度：
  1.151±0.06 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：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-dimethoxynaphthalene-6-carboxylate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.5h， 生成 6,7-Dimethoxy-naphthalene-2-carbaldehyde
  参考文献：
  名称：

  C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors

  摘要：

  A series of 1- and 4-(2-naphthylmethyl)-1H-imidazoles (3 and 4) has been synthesized and evaluated as C-17,C-20-lyase inhibitors. Several 6-methoxynaphthyl derivatives showed potent C-17,C-20-lyase inhibition, suppression of testosterone biosynthesis in rats and reduction in the weight of prostate and seminal vesicles in rats, whereas most of these compounds increased the liver weight after consecutive administrations. The effect on the liver weight was removed by incorporation of a hydroxy group and an isopropyl group at the methylene bridge, as seen in (S)-28d and (S)-42. Selectivity for C-17,C-20-lyase over 11beta-hydroxylase is also discussed, and (S)-42 was found to be a more than 260-fold selective inhibitor. Furthermore, (S)-42 showed a potent suppression of testosterone biosynthesis after a single oral administration in monkeys. These data suggest that (S)-42 may be a promising agent for the treatment of androgen-dependent prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.016
• 作为产物：
  描述：

  4-(3,4-二甲氧基)苯基丁酸乙酯 在 mineral acid 、 硫酸 作用下， 生成 ethyl 2,3-dimethoxynaphthalene-6-carboxylate
  参考文献：
  名称：

  吗啡和间吧酮的可能降解产物的合成；三，

  摘要：

  DOI：

  10.1021/ja01200a049

文献信息

• 合成萘环衍生物和苯并杂环类化合物的方法
  申请人：陕西师范大学

  公开号：CN104478723B

  公开（公告）日：2016-08-24

  本发明公开了一种合成萘环衍生物和苯并杂环类化合物的方法，该方法是将邻位具有α,β‑不饱和酯的芳基醛和酮类化合物在叔胺、叔膦类有机小分子催化剂的催化下发生类似Mortia‑Baylis‑Hillman的反应，进而失去一分子水生成萘环衍生物或苯并杂环类化合物。本发明操作步骤简单，所用催化剂廉价易得，对环境无害，以较好的收率合成了一系列萘环衍生物和苯并杂环类化合物。
• Naphthalene derivatives, their production and use
  申请人：——

  公开号：US20030236274A1

  公开（公告）日：2003-12-25

  A composition containing a compound of the formula: 1 wherein A is a nitrogen-containing heterocyclic group which may be substituted, R 1 is a hydrogen atom, hydrocarbon group which may be substituted, or monocyclic aromatic heterocyclic group which may be substituted, R 2 is a hydrogen atom or a lower alkyl group which may be substituted, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently a hydrogen atom, a hydrocarbon group which may be substituted, a hydroxy group which may be substituted, a thiol group which may be substituted, an amino group which may be substituted, an acyl group or a halogen atom, a salt thereof or a prodrug thereof has steroid C 17,20 -lyase inhibitory activity, and are useful for preventing and treating a mammal suffering from, for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  一种含有化合物的组合物，该化合物的分子式为：1其中A是一种含氮杂环基团，可以被取代，R1是氢原子、可以被取代的碳氢基团或可以被取代的单环芳杂环基团，R2是氢原子或可以被取代的低碳基基团，R3、R4、R5、R6、R7、R8和R9分别为氢原子、可以被取代的碳氢基团、可以被取代的羟基、可以被取代的硫醇基、可以被取代的氨基、酰基或卤素原子，它们的盐或前药具有类固醇C17,20-裂解酶抑制活性，并且可用于预防和治疗患有例如恶性肿瘤的原发性癌症、其转移和复发的哺乳动物。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE NAPHTHALENE DERIVATIVE AND OPTICAL RESOLVER THEREFOR
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1227085B1

  公开（公告）日：2006-03-15
• Gaur, S. P.; Jain, Padam C.; Anand, Nitya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 1, p. 46 - 51
  作者：Gaur, S. P.、Jain, Padam C.、Anand, Nitya

  DOI：——

  日期：——
• Synthesis of Functionalized Naphthalenes from Substituted 1-Methoxybenzocyclobutenes
  作者：Neil G. Andersen、Shawn P. Maddaford、Brian A. Keay

  DOI：10.1021/jo951978v

  日期：1996.1.1