(E)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-phenyl-1-(4-pyridyl)ethene | 162543-81-9

• 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: (E)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-phenyl-1-(4-pyridyl)ethene
• 英文别名: 4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)-2-phenylethenyl]pyridine；4-[(E)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethenyl]pyridine
• CAS: 162543-81-9
• 化学式: C₂₅H₂₅NO₂
• 分子量: 371.479
• InChiKey: HVDREXZQOJJRAC-HAVVHWLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-phenyl-1-(4-pyridyl)ethene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 100.0 ℃ 、10.13 MPa 条件下， 反应 21.0h， 以90%的产率得到4-[2-(3-cyclopentyloxy-4-methoxyphenyl)-2-(phenyl)ethyl]pyridine
  参考文献：
  名称：

  Rapid Synthesis of CDP840 with 2-Pyrimidyl Vinyl Sulfide as a Platform

  摘要：

  A rapid synthesis of CDP840 (a potential therapeutic agent for asthma), using 2-pyrimidyl vinyl sulfide as a platform, has been established. This method includes a stereoselective double Mizoroki-Heck-type arylation, a Liebeskind-Srogl-type cross-coupling reaction, and a Pd/C-catalyzed hydrogenation.

  DOI：

  10.1021/jo0510437
• 作为产物：
  描述：

  3-环戊氧-4-甲氧基苯甲醛 在 叔丁基过氧化氢 、 ruthenium trichloride 、 甲烷磺酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 8.5h， 生成 (E)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-phenyl-1-(4-pyridyl)ethene
  参考文献：
  名称：

  Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn Selective Reduction of an Epoxide

  摘要：

  An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the "skewed side-on approach model" proposed by Jacobsen. LiBK4 . BH3 reduction of the epoxides was found to proceed with retention of configuration.

  DOI：

  10.1021/jo971476c

文献信息

• Tri-substituted phenyl derivatives and processes for their preparation
  申请人：Celltech Therapeutics, Limited

  公开号：US20020143011A1

  公开（公告）日：2002-10-03

  Compounds of general formula (1) are described: 1 wherein ═W— is (1) ═C(Y)— where Y is a halogen atom, or an alkyl or —XR a group where X is —O—, —S(O) m —[where m is zero or an integer of value 1 or 2], or —N(R b )—[where R b is a hydrogen atom or an optionally substituted alkyl group] and R a is a hydrogen atom or an optionally substituted alkyl group or, (2) ═N—; L is (1) a —C(R)═C(R 1 )(R 2 ) or [—CH(R)] n CH(R 1 )(R 2 ) group; is (2) a —(X a ) n Alk′Ar′, or Alk′X a Ar′ group; or is (3) X a R 1 ; Z is a group (A), (B), (C) or (D): 2 wherein Ar is a monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen, sulphur or nitrogen atoms; Z 1 is a group —NR 12 C(O)—[where R 12 is a hydrogen atom or an optionally substituted alkyl or (Alk) t Ar group], —C(O)NR 12 —, —NR 12 C(S)—, —C(S)NR 12 —, —C≡C—, —NR 12 SO 2 —, or —SO 2 NR 12 —; Alk is an optionally substituted straight or branched alkyl chain optionally interrupted by an atom or group X; t is zero or an integer of value 1, 2 or 3; R 3 is a hydrogen or a fluorine atom or an optionally substituted straight or branched alkyl group or an OR 11 group [where R 11 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkoxyalkyl, alkanoyl, formyl, carboxamido or thiocarboxamido group]; R 4 is a hydrogen atom or an optionally substituted alkyl, —CO 2 R 8 , —CSNR 9 R 10 , —CN, —CH 2 CN, or —(CH 2 ) t Ar group where t is zero or an integer of value 1, 2 or 3 and Ar is a monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen, sulphur or nitrogen atoms; provided that when L is a group of type (2) or (3) above then Z is a group of type (A) or type (B) in which R 4 is a —(CH 2 ) t Ar group; R 5 is a group —(CH 2 ) t Ar; R 6 is a hydrogen or a fluorine atom, or an optionally substituted alkyl or —CO 2 R 8 , —CONR 9 R 10 , —CSNR 9 R 10 , —CN or —CH 2 CN group; R 7 is a hydrogen or a fluorine atom, an optionally substituted straight or branched alkyl group, or an OR c group where R c is a hydrogen atom or an optionally substituted alkyl or alkenyl group, alkoxyalkyl, alkanoyl, formyl, carboxamido or thiocarboxamido group; and the salts, solvates, hydrates, prodrugs and N-oxides thereof. Compounds according to the invention are phosphodiesterase type IV inhibitors and are useful in the prophylaxis and treatment of disease such as asthma where unwanted inflammatory response or muscular spasm is present.

  描述了通式(1)的化合物：其中═W—是(1)═C(Y)—，其中Y是卤素原子，或烷基或—XRa基团，其中X是—O—，—S(O)m—[m为0或值为1或2的整数]，或—N(Rb)—[其中Rb是氢原子或可选取代的烷基基团]，而Ra是氢原子或可选取代的烷基基团；或(2)═N—；L是(1)一个—C(R)═C(R1)(R2)或[—CH(R)]nCH(R1)(R2)基团；是(2)一个—(Xa)nAlk′Ar′或Alk′XaAr′基团；或是(3)XaR1；Z是(A)、(B)、(C)或(D)基团：其中Ar是一个单环或双环芳基基团，可选包含一个或多个从氧、硫或氮原子中选择的杂原子；Z1是一个基团—NR12C(O)—[其中R12是氢原子或可选取代的烷基或(Alk)tAr基团]、—C(O)NR12—、—NR12C(S)—、—C(S)NR12—、—C≡C—、—NR12SO2—或—SO2NR12—；Alk是一个可选取代的直链或支链烷基链，可选由一个原子或基团X中断；t为0或值为1、2或3的整数；R3是氢或氟原子或可选取代的直链或支链烷基基团或OR11基团[其中R11是氢原子或可选取代的烷基、烯基、烷氧基烷基、烷酰基、甲酰基、羧酰胺或硫代羧酰胺基团]；R4是氢原子或可选取代的烷基、—CO2R8、—CSNR9R10、—CN、—CH2CN或—(CH2)tAr基团，其中t为0或值为1、2或3的整数，而Ar是一个单环或双环芳基基团，可选包含一个或多个从氧、硫或氮原子中选择的杂原子；但当L是上述类型(2)或(3)的基团时，Z是类型(A)或类型(B)的基团，其中R4是—(CH2)tAr基团；R5是一个基团—(CH2)tAr；R6是氢或氟原子，或可选取代的烷基或—CO2R8、—CONR9R10、—CSNR9R10、—CN或—CH2CN基团；R7是氢或氟原子、可选取代的直链或支链烷基基团或ORc基团，其中Rc是氢原子或可选取代的烷基或烯基基团、烷氧基烷基、烷酰基、甲酰基、羧酰胺或硫代羧酰胺基团；以及其盐、溶剂化合物、水合物、前药和N-氧化物。本发明的化合物是磷酸二酯酶IV抑制剂，可用于预防和治疗存在不需要的炎症反应或肌肉痉挛的疾病，如哮喘。
• STYRIL DERIVATIVES AND PROCESSES FOR THEIR PREPARATION
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：EP0626957B1

  公开（公告）日：1999-03-03
• TRI-SUBSTITUTED PHENYL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：EP0626939B1

  公开（公告）日：2001-11-07
• TRI-SUBSTITUTED PHENYL DERIVATIVES USEFUL AS PDE IV INHIBITORS
  申请人：Celltech R&D Limited

  公开号：EP0766669B1

  公开（公告）日：2005-04-20
• US5580888A
  申请人：——

  公开号：US5580888A

  公开（公告）日：1996-12-03