(E)-4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethenyl]pyridine | 159088-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethenyl]pyridine
• 英文别名: 4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethenyl]pyridine；4-[(E)-2-(3-cyclopentyloxy-4-methoxyphenyl)ethenyl]pyridine
• CAS: 159088-19-4
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: HXRIEVYIZSBJEH-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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)-4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethenyl]pyridine 在 bis(triphenylphosphine)nickel(II) chloride 、 乙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 生成 4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethyl]pyridine
  参考文献：
  名称：

  Ni-catalyzed nucleophilic conjugate additions of Grignard and organozincate reagents to substituted 4-vinylpyridines. General synthesis of phosphodiesterase IV inhibitors

  摘要：

  Alkyl, aryl, and vinyl Grignard reagents were added to olefin II under Ni(acac)(2) or Cl2Ni(PPh3)(2) catalysis to give products with the general formula I in 74-95% yield. Organozincates gave similar results with Ni(acac), as the catalyst, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10217-4
• 作为产物：
  描述：

  3-环戊氧-4-甲氧基苯甲醛 在 甲烷磺酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 1.75h， 生成 (E)-4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethenyl]pyridine
  参考文献：
  名称：

  Ni-catalyzed nucleophilic conjugate additions of Grignard and organozincate reagents to substituted 4-vinylpyridines. General synthesis of phosphodiesterase IV inhibitors

  摘要：

  Alkyl, aryl, and vinyl Grignard reagents were added to olefin II under Ni(acac)(2) or Cl2Ni(PPh3)(2) catalysis to give products with the general formula I in 74-95% yield. Organozincates gave similar results with Ni(acac), as the catalyst, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10217-4

文献信息

• Tetra-substituted phenyl derivatives and processes for their preparation
  申请人：——

  公开号：US20010034450A1

  公开（公告）日：2001-10-25

  Compounds of general formula (1): 1 are described wherein ═W— is (1) ═C(Y)— where Y is a halogen atom, or an alkyl, or -X a R 1 group where X a is —O—, —S(O) m — [where m is zero or an integer of value 1 or 2], or N(R a )- [where R a is a hydrogen atom or an optionally substituted alkyl group] and R 1 is a hydrogen atom or an optionally substituted alkyl group or, (2) ═N—; X is as described above for X a or is a chain —CR═C(R b )— or [—CH(R)] q —CH(R b )- where R is a hydrogen or a fluorine atom or a methyl group, R b is as described below for R 2 and q is zero or the integer 1; R 2 is (1) an optionally substituted alkyl, alkenyl, cycloalkyl or cycloalkenyl group when X is —O—, —S(O) m — or —N(R a )-; or is (2) when X is other than —O—, —S(O) m — or —N(R a )-, a hydrogen atom, or an optionally substituted straight or branched alkyl, alkenyl or alkynyl, alkoxy, alkylthio, —CO 2 R 9 (where R 9 is a hydrogen atom or an optionally substituted alkyl, aryl or aralkyl group), —CONR 10 R 11 (where R 10 and R 11 which may be the same or different is as described for R 9 ), —CSNR 10 R 11 , —CN or NO 2 group; or R 2 and R b , together with the carbon atom to which they are both attached, are linked to form an optionally substituted cycloalkyl or cycloalkenyl group optionally containing one or more X a atoms or groups; R 3 is an atom or group R 13 or -L 1 R 13 where L 1 is a linker group and R 13 is various substituents; R 4 is a hydrogen atom or is as defined for R 6 ; R 5 is a hydrogen or a fluorine atom, or an OR c group where R c is a hydrogen atom or an optionally substituted straight or branched alkyl, alkenyl, alkoxyalkyl, alkanoyl, formyl, carboxamido, thiocarboxamido, cycloalkyl, or cycloalkenyl group; R 6 is a group —(CH 2 ) n Ar where Ar is an optionally substituted monocyclic or bicyclic aryl ring optionally interrupted by one or more heteroatoms —O—, —S— or —N— and n is zero or the integer 1, 2 or 3; R 7 and R 8 , which may be the same or different, is a hydrogen or a fluorine atom, or an optionally substituted straight or branched alkyl group; and the salts, solvates, prodrugs, hydrates 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 an unwanted inflammatory response or muscular spasm is present.

  描述了一般式（1）：1的化合物，其中═W-是（1）═C（Y）-，其中Y是卤素原子，或烷基，或-XaR1基团，其中Xa是-O-，-S（O）m- [其中m为零或值为1或2的整数]，或N（Ra）- [其中Ra是氢原子或可选择取代的烷基基团]，R1是氢原子或可选择取代的烷基基团或（2）═N-; X如上所述为Xa，或者是链-CR═C（Rb）-或[ -CH（R）] q-CH（Rb）-，其中R是氢或氟原子或甲基基团，Rb如下所述为R2，q为零或整数1; R2是（1）可选择取代的烷基，烯基，环烷基或环烯基基团，当X为-O-，-S（O）m-或-N（Ra）-时；或（2）当X不是-O-，-S（O）m-或-N（Ra）-时，是氢原子，或可选择取代的直链或支链烷基，烯基或炔基，烷氧基，烷硫基，-CO2R9（其中R9是氢原子或可选择取代的烷基，芳基或芳基烷基），-CONR10R11（其中R10和R11可以相同或不同，如R9所述），-CSNR10R11，-CN或NO2基团; 或R2和Rb与它们都连接的碳原子一起形成可选择取代的环烷基或环烯基基团，可选地含有一个或多个Xa原子或基团; R3是一个原子或基团R13或-L1R13，其中L1是连接基团，R13是各种取代基; R4是氢原子或如R6所定义的基团; R5是氢或氟原子，或ORc基团，其中Rc是氢原子或可选择取代的直链或支链烷基，烯基，烷氧基，烷酰基，甲酰基，羧酰胺，硫代羧酰胺，环烷基或环烯基基团; R6是-（CH2）nAr基团，其中Ar是可选择取代的单环或双环芳基环，可选择地被一个或多个杂原子-O-，-S-或-N-中断，n为零或整数1,2或3; R7和R8，可以相同或不同，是氢或氟原子，或可选择取代的直链或支链烷基; 以及它们的盐，溶剂化合物，前药，水合物和N-氧化物。根据本发明的化合物是磷酸二酯酶IV抑制剂，可用于预防和治疗疾病，如哮喘，在该疾病中存在不需要的炎症反应或肌肉痉挛。
• 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。
• STYRYL DERIVATIVES, THEIR PREPARATION AND USE AS PDE-IV INHIBITORS
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：EP0640070B1

  公开（公告）日：1997-09-10
• TRISUBSTITUTED PHENYL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS AND PROCESSES FOR THEIR PREPARATION
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：EP0640065B1

  公开（公告）日：2001-10-17
• TRI-SUBSTITUTED PHENYL DERIVATIVES USEFUL AS PDE IV INHIBITORS
  申请人：Celltech R&D Limited

  公开号：EP0766670B1

  公开（公告）日：2002-03-27