(2E, 4E)-5-(2-chlorophenyl)-2,4-pentadien-1-ol | 117308-02-8

• 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: (2E, 4E)-5-(2-chlorophenyl)-2,4-pentadien-1-ol
• 英文别名: (2E,4E)-5-(2-chlorophenyl)penta-2,4-dien-1-ol
• CAS: 117308-02-8
• 化学式: C₁₁H₁₁ClO
• 分子量: 194.661
• InChiKey: IGAQIXATRSPPRL-IJIVKGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E, 4E)-5-(2-chlorophenyl)-2,4-pentadien-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， 25.0~140.0 ℃ 、5.07 MPa 条件下， 反应 3.0h， 生成 2-Acetoxy-2'-chlorobiphenyl
  参考文献：
  名称：

  Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates

  摘要：

  Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140-degrees-C under 50 atm of CO. No five-membered ring products were observed. A platinum complex PtCl2(PPh3)2 was also effective as a catalyst. The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3, 5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51% yield on heating to 160-degrees-C under 50 atm of CO in the presence of NEt3 and Ac2O. Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates. On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)-benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO molecules, respectively.

  DOI：

  10.1021/jo00076a051
• 作为产物：
  描述：

  (2E,4E)-5-(2-Chloro-phenyl)-penta-2,4-dienoic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (2E, 4E)-5-(2-chlorophenyl)-2,4-pentadien-1-ol
  参考文献：
  名称：

  Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates

  摘要：

  Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140-degrees-C under 50 atm of CO. No five-membered ring products were observed. A platinum complex PtCl2(PPh3)2 was also effective as a catalyst. The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3, 5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51% yield on heating to 160-degrees-C under 50 atm of CO in the presence of NEt3 and Ac2O. Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates. On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)-benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO molecules, respectively.

  DOI：

  10.1021/jo00076a051

文献信息

• Imidazolidinones as brain activators
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04886817A1

  公开（公告）日：1989-12-12

  This invention relates to imidazolidinone compounds of the formula ##STR1## wherein Q is methylene group or a single bond: R is a heterocyclic group selected from the group consisting of pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl and 1,3-thiazolyl which may be unsubstituted or with a substituent selected from the group consisting of lower alkyl, lower alkoxy and halogen atom, wherein R is bonded to Q or, when Q is a single bond, to the imidazolidinone ring, through the carbon atom of R; the ring A is an unsubstituted phenyl or a substituted phenyl having 1 or 2 substituent(s) selected from the group consisting of lower alkyl, lower alkoxy, halogen, lower alkylthio, trihalogeno-lower alkyl and nitro; Y is vinylene group or ethynylene; m is a integer from 1 to 6 and n is 0, 1 or 2, or a pharmacetically acceptable salt thereof. These compounds aer useful as cerebral activators, anti-depressants and nootropic drugs.

  这项发明涉及公式为##STR1##的咪唑啉酮化合物，其中Q是亚甲基基团或单键：R是从吡啶基、吡啶并嗪基、嘧啶基、吡嗪基和1,3-噻唑基中选择的杂环基团，可以是未取代或带有从低烷基、低烷氧基和卤原子中选择的取代基，其中R与Q结合，或者当Q为单键时，与咪唑啉酮环通过R的碳原子结合；环A是未取代苯基或具有1或2个取代基（从低烷基、低烷氧基、卤素、低烷硫基、三卤代低烷基和硝基中选择）的取代苯基；Y是乙烯基或乙炔基；m是从1到6的整数，n为0、1或2，或其药用盐。这些化合物可用作脑活化剂、抗抑郁药和脑力药物。
• Asymmetric Auto‐Tandem Palladium Catalysis for 2,4‐Dienyl Carbonates: Ligand‐Controlled Divergent Synthesis
  作者：Jian‐Xiang Zhu、Zhi‐Chao Chen、Wei Du、Ying‐Chun Chen

  DOI：10.1002/anie.202200880

  日期：2022.4.19

  The diastereodivergent assembly of polyhydro-1,6-naphthyridines from o-TosylNH aldimines and 2,4-dienyl carbonates has been realized by ligand-controlled auto-tandem palladium catalysis, through an N-allylation, vinylogous addition, π-σ-π isomerization, and N-allylation cascade. Further tuning of the ligands even allowed regiodivergent azetidine or chemodivergent β-H elimination products to be obtained

  通过配体控制的自串联钯催化，通过 N-烯丙基化、乙烯基加成、π-σ-π，实现了由o - TosylNH 醛亚胺和 2,4-二烯基碳酸酯合成polyhydro-1,6-naphthyridines 的非对映发散组装异构化和N-烯丙基化级联。配体的进一步调整甚至允许获得区域发散的氮杂环丁烷或化学发散的β-H消除产物。
• TAKEDA, MIKIO;INAGE, MASARU;WADA, HIROSHI;TAMAKI, HAJIME;OCHIAI, TAKASHI
  作者：TAKEDA, MIKIO、INAGE, MASARU、WADA, HIROSHI、TAMAKI, HAJIME、OCHIAI, TAKASHI

  DOI：——

  日期：——
• Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates
  作者：Youichi Ishii、Chao Gao、Wen Xiang Xu、Masakazu Iwasaki、Masanobu Hidai

  DOI：10.1021/jo00076a051

  日期：1993.11

  Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140-degrees-C under 50 atm of CO. No five-membered ring products were observed. A platinum complex PtCl2(PPh3)2 was also effective as a catalyst. The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3, 5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51% yield on heating to 160-degrees-C under 50 atm of CO in the presence of NEt3 and Ac2O. Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates. On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)-benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO molecules, respectively.