ethyl (E)-5,5-diphenylpenta-2,4-dienoate | 120342-72-5

• 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: ethyl (E)-5,5-diphenylpenta-2,4-dienoate
• 英文别名: (E)-5,5-diphenyl-2,4-pentadieneoic acid ethyl ester；Ethyl (2E)-5,5-diphenyl-2,4-pentadienoate；ethyl (2E)-5,5-diphenylpenta-2,4-dienoate
• CAS: 120342-72-5
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: IUXFKVZESJQTGH-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (E)-5,5-diphenylpenta-2,4-dienoate 在 吡啶 、 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 diethyl (E)-5,5-diphenyl-2,4-pentadienylphosphate
  参考文献：
  名称：

  磷酸烯丙酯与甲硅烷基硼酸酯的甲硅烷基化环丙烷化

  摘要：

  已经开发了一种由钾（双（三甲基甲硅烷基）酰胺介导的烯丙基磷酸酯与甲硅烷基硼酸酯的环丙烷化反应）。与报道的铜催化的烯丙基取代反应不同，亲核试剂在当前反应条件下选择性攻击烯丙基底物的β位置。还已经研究了该过程的机理，从而表明甲硅烷基钾物质作为活性亲核组分的参与。

  DOI：

  10.1002/anie.201403726
• 作为产物：
  描述：

  反式-4-氧基-2-丁烯酸乙酯 在 四(三苯基膦)钯 、 sodium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 ethyl (E)-5,5-diphenylpenta-2,4-dienoate
  参考文献：
  名称：

  Discovery of Novel 5,5-Diarylpentadienamides as Orally Available Transient Receptor Potential Vanilloid 1 (TRPV1) Antagonists

  摘要：

  We have developed a novel and potent chemical series of 5,5-diphenylpentadienamides for targeting TRPV1 in vitro and in vivo. In this investigation, we examined a variety of replacements for the S-position of dienamides with the goal of addressing issues related to pharmacokinetics. Our data suggest that substitution with alkoxy groups on the phenyl ring at the S-position increases their ability to penetrate the blood brain barrier. This investigation culminated in the discovery of compound (R)-36b, which showed a good pharmacokinetic profile. In vivo, compound (R)-36b was found to be effective at reversing mechanical allodynia in rats in a dose-dependent manner, and it reversed thermal hyperalgesia in a model of neuropathic pain induced by sciatic nerve injury.

  DOI：

  10.1021/jm300101n

文献信息

• Highly Stereoselective Synthesis of 1,3-Dienes through an Aryl to Vinyl 1,4-Palladium Migration/Heck Sequence
  作者：Tian-Jiao Hu、Meng-Yao Li、Qian Zhao、Chen-Guo Feng、Guo-Qiang Lin

  DOI：10.1002/anie.201801963

  日期：2018.5.14

  An efficient aryl to vinyl 1,4‐palladium migration/Heck sequence was developed for the stereoselective synthesis of 1,3‐dienes. High stereoselectivity was observed not only for 1,3‐dienes bearing two similar aryl groups at terminal positions, but also for those with configurations shown to be unfavorable with previous methods.

  开发了一种有效的芳基到乙烯基1,4-钯迁移/ Heck序列，用于1,3-二烯的立体选择性合成。不仅对于在末端位置带有两个相似芳基的1,3-二烯，还观察到了较高的立体选择性，而且对那些构型显示不利于先前方法的化合物也观察到了高立体选择性。
• Cobalt‐Catalyzed Reductive Dimethylcyclopropanation of 1,3‐Dienes
  作者：Jacob Werth、Christopher Uyeda

  DOI：10.1002/anie.201807542

  日期：2018.10.15

  variant of the Simmons–Smith reaction that enables the efficient dimethylcyclopropanation of 1,3‐dienes using a Me2CCl2/Zn reagent mixture. The reactions proceed with high regioselectivity based on the substitution pattern of the 1,3‐diene. The products are vinylcyclopropanes, which serve as substrates for transition‐metal‐catalyzed ring‐opening reactions, including 1,3‐rearrangement and [5+2] cycloaddition

  二甲基环丙烷是有价值的合成靶标，使用锌类胡萝卜素试剂难以获得高收率。在本文中，我们描述了席梦思-史密斯反应的钴催化变体，该变体使用Me 2 CCl 2 / Zn试剂混合物能够有效地进行1,3-二烯的二甲基环丙烷化。根据1,3-二烯的取代模式，反应具有很高的区域选择性。产品是乙烯基环丙烷，可作为过渡金属催化的开环反应的底物，包括1,3重排和[5 + 2]环加成反应。初步研究表明，在钴催化条件下，中等活化度的单烯烃也适用于二甲基环丙烷化。
• Expedient Synthesis of Fused Azepine Derivatives Using a Sequential Rhodium(II)-Catalyzed Cyclopropanation/1-Aza-Cope Rearrangement of Dienyltriazoles
  作者：Erica E. Schultz、Vincent N. G. Lindsay、Richmond Sarpong

  DOI：10.1002/anie.201405356

  日期：2014.9.8

  reported. The process involves an intramolecular cyclopropanation of an α‐imino rhodium(II) carbenoid, leading to a transient 1‐imino‐2‐vinylcyclopropane intermediate which rapidly undergoes a 1‐aza‐Cope rearrangement to generate fused dihydroazepine derivatives in moderate to excellent yields. The reaction proceeds with similar efficiency on gram scale. The use of catalyst‐free conditions leads to the formation

  报道了一种从带有系链二烯的 1-磺酰基-1,2,3-三唑形成稠合二氢氮杂卓衍生物的一般方法。该过程涉及 α-亚氨基铑 (II) 类卡宾的分子内环丙烷化，产生短暂的 1-亚氨基-2-乙烯基环丙烷中间体，该中间体迅速发生 1-氮杂-Cope 重排，以中等至优异的产率生成稠合二氢氮杂卓衍生物。该反应在克规模上以类似的效率进行。使用无催化剂条件导致形成新的 [4.4.0] 双环杂环。
• Catalytic Reactions of Carbene Precursors on Bulk Gold Metal
  作者：Yibo Zhou、Brian G. Trewyn、Robert J. Angelici、L. Keith Woo

  DOI：10.1021/ja900653s

  日期：2009.8.26

  Bulk gold metal powder, consisting of particles (5-50 microm) much larger than nanoparticles, catalyzes the coupling of carbenes generated from diazoalkanes (R(2)C=N(2)) and 3,3-diphenylcyclopropene (DPCP) to form olefins. It also catalyzes cyclopropanation reactions of these carbene precursors with styrenes. The catalytic activity of the gold powder depends on the nature of the gold particles, as

  散装金金属粉末，由比纳米粒子大得多的粒子 (5-50 微米) 组成，催化重氮烷烃 (R(2)C=N(2)) 和 3,3-二苯基环丙烯 (DPCP) 产生的卡宾的耦合形成烯烃。它还催化这些卡宾前体与苯乙烯的环丙烷化反应。金粉的催化活性取决于金颗粒的性质，这由 TEM 和 SEM 研究确定。可以从涉及生成卡宾 R(2)C：吸附在金表面上的中间体的机制来理解这些反应。
• Pentadieneamide compounds which have useful activity of treating a
  申请人：Hoffmann-La Roche Inc.

  公开号：US04975438A1

  公开（公告）日：1990-12-04

  Compounds of the formula ##STR1## Y is O or S, *A is paraphenylene or *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het, Aryl, R.sub.3, R.sub.4 and R.sub.8, independently, are hydrogen, lower alkyl, aryl, R.sub.5 and R.sub.6, independently, are hydrogen or lower alkyl, R.sub.7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment, and when R.sub.6 and R.sub.7 are different, their enantiomers and racemic mixtures thereof, when R.sub.1 and R.sub.2 are different, their geometric isomers, and pharmaceutically acceptable acid addition salts thereof, are described. The compounds of formula I exhibit activity as platelet activating factor (PAF) antagonists and are, therefore, useful in disease states characterized by excess platelet activating factor or for the prevention and treatment of cardiovascular diseases, pulmonary diseases, immunological disorders, inflammatory diseases, dermatological disorders, shock or transplant rejection.

  式为##STR1##的化合物，其中Y是O或S，*A是对苯基或*--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --，X是O，S或--CH.dbd.CH--，n或r分别是独立的0至3的整数，s是0至1的整数，m是0至1的整数，但当m为1时，n+s必须至少为2，R.sub.1和R.sub.2分别是氢，低烷基，环烷基，低烯基，Het，Aryl，R.sub.3、R.sub.4和R.sub.8分别是氢，低烷基，芳基，R.sub.5和R.sub.6分别是氢或低烷基，R.sub.7是氢，低烷基，环烷基，Het-低烷基或芳基，Het是一种单环5-或6-成员杂芳基或含有一或两个异原子（氮、氧和硫）的双环杂芳基基团，该基团可以被低烷基，卤素或芳基取代，星号表示连接点，当R.sub.6和R.sub.7不同时，它们的对映异构体和混合物，当R.sub.1和R.sub.2不同时，它们的几何异构体以及药学上可接受的酸盐也被描述。公式I的化合物表现为血小板活化因子（PAF）拮抗剂的活性，因此，它们对于具有过量血小板活化因子的疾病状态或预防和治疗心血管疾病，肺部疾病，免疫性疾病，炎症性疾病，皮肤病，休克或移植排斥反应是有用的。