methyl 4-iodo-3-(methoxymethoxy)benzoate | 216444-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-iodo-3-(methoxymethoxy)benzoate
• 英文别名: Methyl 3-methoxymethoxy-4-iodobenzoate
• CAS: 216444-11-0
• 化学式: C₁₀H₁₁IO₄
• 分子量: 322.099
• InChiKey: WTRGIGUGMJTPPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  methyl 4-iodo-3-(methoxymethoxy)benzoate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 16.0h， 生成 4-碘-3-(甲氧基甲氧基)苯甲酸
  参考文献：
  名称：

  Spirocyclic Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of N,N-Diethyl-3-hydroxy-4-(spiro[chromene-2,4′-piperidine]-4-yl) Benzamide (ADL5747)

  摘要：

  Selective, nonpeptidic delta opioid receptor agonists have been the subject of great interest as potential novel analgesic agents. The discoveries of BW373U86 (1) and SNC80 (2) contributed to the rapid expansion of research in this field. However, poor drug-like properties and low therapeutic indices have prevented clinical evaluation of these agents. Doses of I and 2 similar to those required for analgesic activity produce convulsions in rodents and nonhuman primates. Recently, we described a novel series of potent, selective. and orally bioavailable delta opioid receptor agonists. The lead derivative, ADL5859 (4), is currently in phase It proof-of-concept studies for the management of pain. Further structure activity relationship exploration has led to the discovery of ADL5747 (36), which is approximately 50-fold more potent than 4 in an animal model of inflammatory pain. On the basis of its favorable efficacy, safety, and pharmacokinetic profile, 36 was selected as a clinical candidate for the treatment of pain.

  DOI：

  10.1021/jm900773n
• 作为产物：
  描述：

  氯甲基甲基醚 、 3-羟基-4-碘苯甲酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 4-iodo-3-(methoxymethoxy)benzoate
  参考文献：
  名称：

  双光氧化还原/金催化芳基重氮盐对邻炔基苯酚的芳香环化：苯并呋喃的灵活合成

  摘要：

  描述了一种通过双重光氧化还原/金催化的芳基重氮盐对邻炔基苯酚进行芳基环化的新方法。反应在室温下在没有碱和/或添加剂的情况下平稳进行，并为苯并呋喃衍生物提供了一种有效的方法。转换的范围很广，并讨论了局限性。提议该反应通过光还原还原产生的乙烯基金（III）中间体进行，该中间体经过还原消除以提供杂环偶联加合物。

  DOI：

  10.1021/acs.joc.6b01060

文献信息

• Triaromatic compounds and pharmaceutical/cosmetic compositions comprised
  申请人：Centre International de Recherches Dermatologiques

  公开号：US06150413A1

  公开（公告）日：2000-11-21

  Novel pharmaceutically/cosmetically-active triaromatic compounds have the structural formula (I): ##STR1## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.

  新型具有药用/化妆作用的三芳基化合物的结构式（I）如下：##STR1##，可用于治疗各种疾病状态，无论是人类还是兽医，例如皮肤病、风湿病、呼吸系统疾病、心血管疾病、骨骼疾病和眼科疾病，以及哺乳动物皮肤和毛发状况/疾病的治疗。
• US6150413A
  申请人：——

  公开号：US6150413A

  公开（公告）日：2000-11-21
• Spirocyclic Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of <i>N</i>,<i>N</i>-Diethyl-3-hydroxy-4-(spiro[chromene-2,4′-piperidine]-4-yl) Benzamide (ADL5747)
  作者：Bertrand Le Bourdonnec、Rolf T. Windh、Lara K. Leister、Q. Jean Zhou、Christopher W. Ajello、Minghua Gu、Guo-Hua Chu、Paul A. Tuthill、William M. Barker、Michael Koblish、Daniel D. Wiant、Thomas M. Graczyk、Serge Belanger、Joel A. Cassel、Marina S. Feschenko、Bernice L. Brogdon、Steven A. Smith、Michael J. Derelanko、Steve Kutz、Patrick J. Little、Robert N. DeHaven、Diane L. DeHaven-Hudkins、Roland E. Dolle

  DOI：10.1021/jm900773n

  日期：2009.9.24

  Selective, nonpeptidic delta opioid receptor agonists have been the subject of great interest as potential novel analgesic agents. The discoveries of BW373U86 (1) and SNC80 (2) contributed to the rapid expansion of research in this field. However, poor drug-like properties and low therapeutic indices have prevented clinical evaluation of these agents. Doses of I and 2 similar to those required for analgesic activity produce convulsions in rodents and nonhuman primates. Recently, we described a novel series of potent, selective. and orally bioavailable delta opioid receptor agonists. The lead derivative, ADL5859 (4), is currently in phase It proof-of-concept studies for the management of pain. Further structure activity relationship exploration has led to the discovery of ADL5747 (36), which is approximately 50-fold more potent than 4 in an animal model of inflammatory pain. On the basis of its favorable efficacy, safety, and pharmacokinetic profile, 36 was selected as a clinical candidate for the treatment of pain.
• Dual Photoredox/Gold Catalysis Arylative Cyclization of <i>o</i>-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans
  作者：Zhonghua Xia、Omar Khaled、Virginie Mouriès-Mansuy、Cyril Ollivier、Louis Fensterbank

  DOI：10.1021/acs.joc.6b01060

  日期：2016.8.19

  A new method for the arylative cyclization of o-alkynylphenols with aryldiazonium salts via dual photoredox/gold catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives and offers an efficient approach to benzofuran derivatives. The scope of the transformation is wide, and the limitations are discussed. The reaction is proposed to proceed through

  描述了一种通过双重光氧化还原/金催化的芳基重氮盐对邻炔基苯酚进行芳基环化的新方法。反应在室温下在没有碱和/或添加剂的情况下平稳进行，并为苯并呋喃衍生物提供了一种有效的方法。转换的范围很广，并讨论了局限性。提议该反应通过光还原还原产生的乙烯基金（III）中间体进行，该中间体经过还原消除以提供杂环偶联加合物。