N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide | 74007-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide
• 英文别名: 2-(3-hydroxy-4-methoxyphenyl)-N-[2-(3-methoxyphenyl)ethyl]acetamide；N-(3-Methoxy-phenethyl)-3-hydroxy-4-methoxy-phenylacetamid；3-Hydroxy-4-methoxy-N-[2-(3-methoxyphenyl)ethyl]benzeneacetamide
• CAS: 74007-21-9
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: OMDAQWLOORIMIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  570.6±50.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide 在 氟化铵 、 三氟甲磺酸 、 氢氟酸 、 氨 、 lithium 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 氯仿 、 叔丁醇 为溶剂， 生成 (+/-)-dihydrocodeinone
  参考文献：
  名称：

  Synthetic opium alkaloids and derivatives. A short total synthesis of (.+-.)-dihydrothebainone, (.+-.)-dihydrocodeinone, and (.+-.)-nordihydrocodeinone as an approach to a practical synthesis of morphine, codeine, and congeners

  摘要：

  DOI：

  10.1021/jo01303a045
• 作为产物：
  描述：

  对甲氧基苯乙酸 在 copper(II) sulfate sodium hydroxide 、 溴 、 iron(II) bromide 作用下， 以 氯仿 、 水 为溶剂， 反应 278.0h， 生成 N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide
  参考文献：
  名称：

  Preparation of oxygenated phenylacetic acids

  摘要：

  DOI：

  10.1021/jo00185a061

文献信息

• Preparation of amides from an acid and amine for intermediates in the synthesis of morphinans
  申请人：Mallinckrodt Inc.

  公开号：EP2177504A1

  公开（公告）日：2010-04-21

  The present invention is directed to processes for the synthesis of morphinans. In particular, a process for coupling a carboxylic acid compound with an amine compound to form an amide product that can then be isolated or the crude amide product can be cyclized to form a 3,4-dihydroisoquinoline. In one embodiment, the carboxylic acid contains a phenol moiety protected with a labile protecting group. The protected phenol reduces reaction times, simplifies work-up of the product, and reduces the amount of cyclizing agent, POCl3 that is necessary to form the 3,4-dihydroisoquinoline.

  本发明涉及吗啡类化合物的合成工艺。特别是一种将羧酸化合物与胺化合物偶联形成酰胺产物的工艺，该酰胺产物可以分离出来，或者将粗酰胺产物环化形成3,4-二氢异喹啉。在一个实施方案中，羧酸含有一个用易变保护基团保护的苯酚分子。受保护的苯酚可缩短反应时间，简化产品的加工，并减少形成 3,4-二氢异喹啉所需的环化剂 POCl3 的用量。
• Process for the preparation of 3,4-dihydroisoquinolines in the synthesis of morphinans
  申请人：Mallinckrodt Inc.

  公开号：EP2161253A2

  公开（公告）日：2010-03-10

  The present invention is directed to processes for the synthesis of morphinans. In particular, a process tor coupling a carboxylic acid compound with an amine compound to form an amide product that can then be isolated or the crude amide product can be cyclized to form a 3,4-dihydroisoquinoline. In one embodiment, the carboxylic acid contains a phenol moiety protected with a labile protecting group. The protected phenol reduces reaction times, simplifies work-up of the product, and reduces the amount of cyclizing agent, POCl3 that is necessary to form the 3,4-dihydroisoquinoline.

  本发明涉及吗啡类化合物的合成工艺。特别是一种将羧酸化合物与胺化合物偶联形成酰胺产物的工艺，这种酰胺产物可以分离出来，或者将粗酰胺产物环化形成 3,4-二氢异喹啉。在一个实施方案中，羧酸含有一个用易变保护基团保护的苯酚分子。受保护的苯酚可缩短反应时间，简化产品的加工，并减少形成 3,4-二氢异喹啉所需的环化剂 POCl3 的用量。
• Meuzelaar, Gerrit J.; Van Vliet, Michiel C. A.; Maat, Leendert, European Journal of Organic Chemistry, 1999, # 9, p. 2315 - 2321
  作者：Meuzelaar, Gerrit J.、Van Vliet, Michiel C. A.、Maat, Leendert、Sheldon, Roger A.

  DOI：——

  日期：——
• A New Class of Selective and Potent 7-Dehydrocholesterol Reductase Inhibitors
  作者：Aline Horling、Christoph Müller、Richard Barthel、Franz Bracher、Peter Imming

  DOI：10.1021/jm3006096

  日期：2012.9.13

  We prepared a number of N-phenethyltetrahydroisoquinolines structurally related to protoberberines. They were tested for activity against bacteria, fungi, and human leukemia HL-60 cells and also for inhibition of biosynthesis: ergosterol in yeasts and cholesterol in human cells. In the latter assay panel, several of the compounds were distinguished by a strong and selective inhibition of 7-dehydrocholesterol reductase (7-DHCR, EC 1.3.1.21), an enzyme responsible for the conversion of 7-dehydrocholesterol to cholesterol in the last step of cholesterol biosynthesis. In a whole-cell assay, the most active compound 5f showed a much stronger inhibition of overall cholesterol biosynthesis (IC50 2.3 nM) than BM 15.766 (IC50 500 nM), presently the most selective known inhibitor of 7-DHCR Since a defect of 7-dehydrocholesterol reductase is associated with Smith-Lemli-Opitz syndrome (SLOS), the potent and selective inhibitors reported here will enable more detailed investigation of the pathogenesis of SLOS.
• WO2008/73390
  申请人：——

  公开号：——

  公开（公告）日：——