2-(cyclopentyloxy)-4-ethynyl-1-methoxybenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(cyclopentyloxy)-4-ethynyl-1-methoxybenzene
• 英文别名: 2-cyclopentyloxy-4-ethynyl-1-methoxybenzene
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: DBKWBPDIAPBLFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(cyclopentyloxy)-4-ethynyl-1-methoxybenzene 在 (R,R,R,R)-Wingphos 、 水 、 palladium(II) acetylacetonate 、 2-(2,8-dimethyl-10H-phenoxaphosphinin-10-yl)pyridine 、 对甲苯磺酸 、 乙酰氯 作用下， 以 1,2-二氯乙烷 为溶剂， 25.0~70.0 ℃ 、3.0 MPa 条件下， 反应 40.0h， 生成 (S)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  钯继电器催化炔烃不对称双羟基羰基化生成手性琥珀酸

  摘要：

  通过结合两种不同的膦配体，以一锅法实现了末端炔烃到手性琥珀酸的 Pd 催化不对称双羟基羰基化反应。炔烃羰基化由非手性单膦决定，以提供支链丙烯酸，而所得中间体进一步经历 Pd/手性双膦催化的对映选择性羟基羰基化。

  DOI：

  10.1002/anie.202204156
• 作为产物：
  描述：

  3-环戊氧-4-甲氧基苯甲醛 在 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 2-(cyclopentyloxy)-4-ethynyl-1-methoxybenzene
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00024a012

文献信息

• Synthesis and anticancer activities of novel 3,5-disubstituted-1,2,4-oxadiazoles
  作者：Dalip Kumar、Gautam Patel、Emmanuel O. Johnson、Kavita Shah

  DOI：10.1016/j.bmcl.2009.03.158

  日期：2009.5

  A series of 3,5-disubstituted-1,2,4-oxadiazoles were synthesized and evaluated for their in vitro anti-proliferative activities against various cancer cell lines. Formation of 1,2,4-oxadiazole ring was accomplished by the reaction of amidoxime with carboxylic acids. The in vitro cytotoxic effects of 3,5-disubstituted-1,2,4-oxadiazoles have been demonstrated across a wide array of tumor cell types and

  合成了一系列3,5-二取代-1,2,4-恶二唑，并评估了它们对各种癌细胞的体外抗增殖活性。1,2,4-恶二唑环的形成是通过of胺肟与羧酸的反应完成的。已在多种肿瘤细胞类型中证明了3,5-二取代-1,2,4-恶二唑的体外细胞毒性作用，一些化合物对胰腺（3f，3h，3j和3k）和前列腺具有特异性（3n）癌细胞。在制备的3,5-二取代-1,2,4-恶二唑中，化合物3n的选择性最高（> 450倍），化合物3p 对前列腺癌细胞系具有最大的细胞毒性（10 nM）。
• [EN] ISOCHROMENONES USEFUL IN THE TREATMENT OF INFLAMMATION<br/>[FR] ISOCHROMÉNONES UTILISABLES DANS LE TRAITEMENT DE L'INFLAMMATION
  申请人：BIOLIPOX AB

  公开号：WO2010076564A2

  公开（公告）日：2010-07-08

  This invention is directed to compounds of formula (I): wherein R1, R2, R3, Rx, Ry, m and n have meanings given in the description, or pharmaceutically acceptable salts, solvates or prodrugs thereof, which are useful as PDE4, PDE7 or PDE4 and PDE7 inhibitors, and therefore useful e.g. in the treatment and/or prevention of diseases and conditions associated with inflammation.
• CN116986961
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Asymmetric Double Hydroxycarbonylation of Alkynes to Chiral Succinic Acids Enabled by Palladium Relay Catalysis
  作者：Xiaolei Ji、Chaoren Shen、Xinxin Tian、Hongru Zhang、Xinyi Ren、Kaiwu Dong

  DOI：10.1002/anie.202204156

  日期：2022.7.18

  phosphine ligands, a Pd-catalyzed asymmetric double hydroxycarbonylation of terminal alkynes to chiral succinic acids was achieved in a one-pot manner. The alkyne carbonylation was dictated by the achiral monophosphine to afford branched acrylic acids, while the resulting intermediates further underwent Pd/chiral bisphosphine-catalyzed enantioselective hydroxycarbonylation.

  通过结合两种不同的膦配体，以一锅法实现了末端炔烃到手性琥珀酸的 Pd 催化不对称双羟基羰基化反应。炔烃羰基化由非手性单膦决定，以提供支链丙烯酸，而所得中间体进一步经历 Pd/手性双膦催化的对映选择性羟基羰基化。