(E)-methyl-3-<3-(cyclopenyloxy)-4-methoxyphenyl>prop-2-enoate | 133332-20-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl-3-<3-(cyclopenyloxy)-4-methoxyphenyl>prop-2-enoate
• 英文别名: (E)-3-(3-cyclopentyloxy-4-methoxyphenyl)acrylic acid methyl ester；(E)-methyl 3-(3-cyclopentoxy-4-methoxyphenyl)prop-2-enoate；methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate；methyl 3-cyclopentyloxy-4-methoxycinnamate；Methyl 3[3-(cyclopentyloxy)-4-methoxyphenyl]acrylate；methyl (E)-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enoate
• CAS: 133332-20-4
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: GFRBHAWHFNSOCC-CSKARUKUSA-N

物化性质

• 熔点：
  54-57 °C
• 沸点：
  409.3±30.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (E)-methyl-3-<3-(cyclopenyloxy)-4-methoxyphenyl>prop-2-enoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (E)-3-(3-环戊氧基-4-甲氧基苯基)-2-丙烯酸
  参考文献：
  名称：

  Synthesis of the Novel Antidepressant (R)-(-)-Rolipram

  摘要：

  Enantioselective synthesis of (R)-Rolipram 1 has been achieved through a conjugate addition of cyanide to enantiomerically pure 2-(2-aryl ethenyl)oxazoline 2, followed by selective reduction of the adduct with NaBH4-NiCl2.

  DOI：

  10.1080/00397919708004171
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 盐酸 、 ammonium tetrafluoroborate 、 水 、 sodium acetate 、 palladium diacetate 、 碳酸氢钠 、 potassium carbonate 、 potassium iodide 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 (E)-methyl-3-<3-(cyclopenyloxy)-4-methoxyphenyl>prop-2-enoate
  参考文献：
  名称：

  从扑热息痛到咯利普兰及其衍生物：脱乙酰基-重氮化序列和钯催化的松田-Heck反应的应用

  摘要：

  摘要 描述了从流行的止痛药4-乙酰氨基苯酚（扑热息痛）六步合成抗抑郁剂咯利普兰。这些步骤包括芳族核的氧化功能化，通过脱乙酰基-重氮化作用，重田松树-Heck反应，共轭添加硝基甲烷和氢化环化形成重氮盐。 描述了从流行的止痛药4-乙酰氨基苯酚（扑热息痛）六步合成抗抑郁剂咯利普兰。这些步骤包括芳族核的氧化功能化，通过脱乙酰基-重氮化作用，重田松树-Heck反应，共轭添加硝基甲烷和氢化环化形成重氮盐。

  DOI：

  10.1055/s-0032-1316874

文献信息

• Trisubstituted phenyl analogs having activity for congestive heart
  申请人：Warner-Lambert Company

  公开号：US04971959A1

  公开（公告）日：1990-11-20

  Novel trisubstituted phenyl analogs are now found to have activity as for the treatment of congestive heart failure.

  新型的三取代苯类类似物现在被发现具有治疗充血性心力衰竭的活性。
• 1-hydroxy-4(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone and
  申请人：Orion-yhtyma Oy

  公开号：US05356923A1

  公开（公告）日：1994-10-18

  ##STR1## Substituted cyclic hydroxamic acids of general formula (I) in which R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen, halogen, lower alkyl, lower alkoxy, cycloalkoxy, aryloxy which is optionally substituted by 1 to 3 halogen, or aralkyloxy, which is optionally substituted by 1 to 3 halogen, or R.sub.1 and R.sub.2 together form a --O--CH.sub.2 --O-- group; with the proviso that R.sub.3 is not hydrogen when R.sub.1 and R.sub.2 are both hydrogen; R.sub.4 and R.sub.5 are independently hydrogen or lower alkyl, R.sub.6 is hydrogen or lower alkyl and physiologically acceptable salts and esters thereof are selective inhibitors of phosphodiesterase IV activity and leukotriene B.sub.4 and C.sub.4 synthesis without showing any significant effect on phosphodiesterase III activity, and are therefore useful in the treatment of hypersensitivity and inflammatory diseases.

  通式（I）中的取代环状羟肟酸，其中R.sub.1、R.sub.2和R.sub.3独立地表示氢、卤素、低烷基、低烷氧基、环烷氧基、取代1至3个卤素的芳氧基，或取代1至3个卤素的芳基烷氧基，或R.sub.1和R.sub.2共同形成--O--CH.sub.2--O--基团；在R.sub.1和R.sub.2均为氢时，R.sub.3不表示氢；R.sub.4和R.sub.5独立地表示氢或低烷基，R.sub.6表示氢或低烷基，其生理上可接受的盐和酯是磷酸二酯酶IV活性和白三烯B.sub.4和C.sub.4合成的选择性抑制剂，而不对磷酸二酯酶III活性显示任何显著影响，因此在治疗过敏和炎症性疾病方面有用。
• Substituted pyrrolidines
  申请人：Glaxo Wellcome Inc.

  公开号：US05665754A1

  公开（公告）日：1997-09-09

  Novel pyrrolidine compounds which are useful for inhibiting the function of Type IV phosphodiesterase (PDE-IV) as well as methods for making the same are disclosed. Applications in treating inflammatory diseases and other diseases involving elevated levels of cytokines, as well as central nervous system (CNS) disorders, are also disclosed.

  本发明涉及一种新型吡咯烷类化合物，可用于抑制第四型磷酸二酯酶（PDE-IV）的功能，以及制备这种化合物的方法。本发明还涉及在治疗炎症性疾病和其他涉及细胞因子水平升高的疾病以及中枢神经系统（CNS）障碍中的应用。
• Bifunctional Iminophosphorane‐Catalyzed Enantioselective Nitroalkane Addition to Unactivated α,β‐Unsaturated Esters
  作者：Daniel Rozsar、Alistair J. M. Farley、Iain McLauchlan、Benjamin D. A. Shennan、Ken Yamazaki、Darren James Dixon

  DOI：10.1002/anie.202303391

  日期：——

  The first intermolecular enantioselective addition of nitroalkanes to unactivated α,β-unsaturated esters is described, catalyzed by a bifunctional iminophosphorane (BIMP) superbase. This fundamental synthetically relevant transformation proceeds with high enantiomeric excesses and yields over a wide range of feedstock substrates, providing pharmaceutically relevant building blocks in a single step

  描述了硝基烷烃与未活化的 α,β-不饱和酯的第一次分子间对映选择性加成，由双功能亚氨基正膦 (BIMP) 超强碱催化。这种基本的合成相关转化在多种原料底物上以高对映体过量和产率进行，只需一步即可提供药学相关的构建模块。
• Design and Synthesis of Conformationally Constrained Analogs of 4-(3-Butoxy-4-methoxybenzyl)imidazolidin-2-one (Ro 20-1724) as Potent Inhibitors of cAMP-Specific Phosphodiesterase
  作者：Marcus F. Brackeen、Jeffrey A. Stafford、David J. Cowan、Peter J. Brown、Paul L. Domanico、Paul L. Feldman、Dudley Rose、Alan B. Strickland、James M. Veal、Margrith Verghese

  DOI：10.1021/jm00024a012

  日期：1995.11

  The synthesis and biological evaluation of cAMP-specific phosphodiesterase (PDE IV) inhibitors is described. The PDE TV inhibitor 4-(3-butoxy-4-methoxybenzyl)imidazolidin (Ro 20-1724, 2) was used as a template from which to design a set of rigid oxazolidinones, imidazolidinones, and pyrrolizidinones that mimic Ro 20-1724 but differ in the orientation of the carbonyl group. The endo isomer of each of these heterocycles was more potent than the exo isomer in an enzyme inhibition assay and a cellular assay, which measured TNF alpha secretion from activated human peripheral blood monocytes (HPBM). Imidazolidinone 4a inhibited human PDE I with a K-i of 27 nM and TNF alpha secretion from HPBM with an IC50 of 290 nM. By comparison, Ro 20-1724 is significantly less active in these assays with activities of 1930 and 1800 nM, respectively.