3-(2-溴-5-甲氧基苯基)丙腈 | 60100-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(2-溴-5-甲氧基苯基)丙腈
• 英文名称: 2-bromo-5-methoxyphenylpropionitrile
• 英文别名: 3-(2-Bromo-5-methoxyphenyl)propanenitrile
• CAS: 60100-18-7
• 化学式: C₁₀H₁₀BrNO
• 分子量: 240.099
• InChiKey: VHHBZCHKVOSUDL-UHFFFAOYSA-N

物化性质

• 沸点：
  363.2±27.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-溴-5-甲氧基苯基)丙腈 在 aluminum (III) chloride 、 正十二烷基甲基硫醚 、 氨 、 sodium amide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 3-羟基双环[4.2.0]辛-1,3,5-三烯-7-甲腈
  参考文献：
  名称：

  Identification of Fused-Ring Alkanoic Acids with Improved Pharmacokinetic Profiles that Act as G Protein-Coupled Receptor 40/Free Fatty Acid Receptor 1 Agonists

  摘要：

  The G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. We previously identified phenylpropanoic acid derivative 1 (3-{4-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl}propanoic acid) as a potent and orally available GPR40/FFA1 agonist; however, 1 exhibited high clearance and low oral bioavailability, which was likely due to its susceptibility to beta-oxidation at the phenylpropanoic acid moiety. To identify long-acting compounds, we attempted to block the metabolically labile sites at the phenylpropanoic acid moiety by introducing a fused-ring structure. Various fused-ring alkanoic acids with potent GPR40/FFA1 activities and good PK profiles were produced. Further optimizations of the lipophilic portion and the acidic moiety led to the discovery of dihydrobenzofuran derivative 53 ((6-{[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methoxy}-2,3-dihydro-1-benzofuran-3-yl)acetic acid), which acted as a GPR40/FFA1 agonist with in vivo efficacy during an oral glucose tolerance test (OGTT) in rats with impaired glucose tolerance.

  DOI：

  10.1021/jm2012968
• 作为产物：
  描述：

  间甲基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 3-(2-溴-5-甲氧基苯基)丙腈
  参考文献：
  名称：

  Total Synthesis of Cortistatins A and J

  摘要：

  This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.

  DOI：

  10.1021/jo2002616
• 作为试剂：
  描述：

  乙腈 、 正丁基锂 、 2-溴-5-甲氧基溴苄 在 氮气 、 乙酸乙酯 、 3-(2-溴-5-甲氧基苯基)丙腈 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以This resulted in 2.29 g (63%) of 3-(2-bromo-5-methoxyphenyl)propanenitrile as a yellow semi-solid的产率得到3-(2-溴-5-甲氧基苯基)丙腈
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

  摘要：

  本文披露了新的杂环化合物和组合物以及它们作为治疗疾病的药物的应用。还提供了抑制人类或动物主体中PAS激酶（PASK）活性的方法，用于治疗糖尿病等疾病。

  公开号：

  US20160229815A1

文献信息

• On the influence of the nature of the iron(III) salt catalyst precursor for the preparation of sodium amide
  作者：Nicolas Galy、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.crci.2010.11.008

  日期：2011.5

  Résumé Our recent experiments, for the formation of sodium amide from liquid ammonia and sodium metal, revealed the necessity to employ Fe(NO3)3•9H2O as the catalyst precursor, and not FeCl3. In the presence of FeCl3, we observed several times the ignition of the mixture during the hydrolysis, and the desired product was not obtained.

  总结 我们最近进行的实验表明，在用液态氨和金属钠合成氨基钠的过程中，需要使用Fe(NO3)3•9H2O作为催化剂前体，而不是FeCl3。在FeCl3存在的情况下，我们多次观察到水解过程中混合物被点燃，而无法得到所需产物。
• Heterocyclic compounds for the inhibition of PASK
  申请人：McCall John M.

  公开号：US08916560B2

  公开（公告）日：2014-12-23

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，并将其应用于作为药物治疗疾病。还提供了抑制人类或动物主体中PAS激酶（PASK）活性的方法，以治疗糖尿病等疾病。
• Synthesis of Diastereomeric 8‐Fluoro‐ABC‐Steroid Building Blocks
  作者：Michael Essers、Günter Haufe

  DOI：10.1002/ejoc.202300206

  日期：——

  Two diastereomeric ABC-building blocks for hitherto widely unknown steroids with a fluorine substituent in 8-position were prepared in a convergent synthesis with eight linear steps from 6-chlorohex-1-ene and a benzocyclobutene derivative. Key step was an intramolecular Diels–Alder reaction of an o-quinodimethane with a fluorine-containing α,β-unsaturated ketone.

  迄今为止，在 8 位具有氟取代基的两个非对映异构体 ABC 构建块在收敛合成中制备，具有八个线性步骤，来自 6-chlorohex-1-ene 和苯并环丁烯衍生物。关键步骤是邻醌二甲烷与含氟 α,β-不饱和酮的分子内 Diels-Alder 反应。
• [EN] HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES POUR L'INHIBITION DE LA PASK
  申请人：BIOENERGENIX

  公开号：WO2011028947A3

  公开（公告）日：2011-08-04
• Trehan, I. R.; Singh, N. P.; Jain, Vinay K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 6, p. 484 - 486
  作者：Trehan, I. R.、Singh, N. P.、Jain, Vinay K.

  DOI：——

  日期：——