methyl (2E)-3-(4-iodophenyl)prop-2-enoate | 161634-73-7

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (2E)-3-(4-iodophenyl)prop-2-enoate
• 英文别名: methyl (E)-3-(4-iodophenyl)acrylate；Methyl (4-iodophenyl)propenoate；methyl (E)-3-(4-iodophenyl)prop-2-enoate
• CAS: 161634-73-7
• 化学式: C₁₀H₉IO₂
• 分子量: 288.085
• InChiKey: IDATZIWFZZIKNZ-QPJJXVBHSA-N

物化性质

• 沸点：
  329.4±25.0 °C(Predicted)
• 密度：
  1.670±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  methyl (2E)-3-(4-iodophenyl)prop-2-enoate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 (2S,3S)-2-(hydroxymethyl)-3-(4-iodophenyl)oxirane
  参考文献：
  名称：

  Total Synthesis of Bouvardin, O-Methylbouvardin, and O-Methyl-N9-desmethylbouvardin

  摘要：

  Concise total syntheses of bouvardin (1) and O-methylbouvardin (2) are described based on the asymmetric synthesis of the N-methyl-erythro-beta-hydroxy-L-4-iodophenylalanine derivative 24, its coupling with the selectively protected N,O-4-dimethyl-L-DOPA methyl ester to provide 40, and subsequent incorporation into a surprisingly successful key Ullmann macrocyclization reaction for preparation of the 14-membered 13 (S)-hydroxycycloisodityrosine subunit 15 of the bicyclic hexapeptides. Coupling of 15 with BOCNH-D-Ala-Ala-NMe-Tyr(OMe)-Ala-OC6F5 followed by 18-membered-ring macrocyclization strategically conducted with formation of a secondary amide at a D-amino acid amine terminus (C-2-N-3 amide) provided O-methylbouvardin (2). Selective demethylation (BBr3) of 2 provided bouvardin (1) in excellent conversion (86%). The extensions of the studies to the preparation of O-methyl-N-9-desmethylbouvardin (51) are detailed and its solution-phase conformational properties examined by H-1 NMR in efforts which confirm that the additional minor conformation of 1 and 2 (ca. 10-15%) observed in nonpolar solvents (CDCl3, THF-d(8)), arise from a cis N-9-C-8 N-methylamide conformation.

  DOI：

  10.1021/ja00098a015
• 作为产物：
  描述：

  methyl (E)-3-(4-(triethylgermyl)phenyl)acrylate 在 N-碘代丁二酰亚胺 作用下， 反应 16.0h， 以73%的产率得到methyl (2E)-3-(4-iodophenyl)prop-2-enoate
  参考文献：
  名称：

  使用三乙基锗烷作为正交掩蔽基团模块化生成（碘化）聚芳烃

  摘要：

  本文公开了一种与广泛采用的 Suzuki 偶联互补的模块化偶联方法，该方法依赖于含有有机锗烷的结构单元与基于空气稳定的 Pd 二聚体的键结构配对，这允许显着缩短反应时间并封闭可接近的化合物空间中的间隙。

  DOI：

  10.1002/anie.202201475

文献信息

• Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones
  作者：Réka J. Faggyas、Megan Grace、Lewis Williams、Andrew Sutherland

  DOI：10.1021/acs.joc.8b01910

  日期：2018.10.19

  A fast and effective one-pot tandem process that generates Heck coupled products from readily available anilines via stable aryl diazonium tosylate salts was developed. The mild and simple procedure involves rapid formation of aryl diazonium salts using a polymer-supported nitrite reagent and p-tosic acid, followed by a base-free Heck–Matsuda coupling with acrylates and styrenes. Using 2-nitroanilines

  开发了一种快速有效的一锅串联方法，该方法可通过稳定的芳基重氮甲苯磺酸盐从易于获得的苯胺生成Heck偶联产物。温和而简单的步骤涉及使用聚合物负载的亚硝酸盐试剂和对羟基苯甲酸酯快速形成芳基重氮盐-甲苯磺酸，然后与丙烯酸酯和苯乙烯进行无碱Heck-Matsuda偶联。使用2-硝基苯胺作为底物，将一锅串联方法扩展到直接合成3,4-二氢喹啉-2-酮。在这种情况下，经过重氮化和Heck-Matsuda偶联生成肉桂酸甲酯，添加氢气并再利用钯催化剂还原硝基和烯烃氢化，可有效形成3,4-二氢喹啉-2-酮。 。一锅四步法的合成效用通过基于喹啉酮的钠离子通道调节剂的五锅法合成得到了证明。
• [EN] METHODS FOR TREATING RETINOID RESPONSIVE DISORDERS USING SELECTIVE INHIBITORS OF CYP26A AND CYP26B<br/>[FR] PROCEDES PERMETTANT DE TRAITER DES TROUBLES SENSIBLES AU RETINOIDE AU MOYEN D'INHIBITEURS SELECTIFS DE CYP26A ET DE CYP26B
  申请人：ALLERGAN INC

  公开号：WO2005058301A1

  公开（公告）日：2005-06-30

  The invention provides methods for treating an individual having a retinoid responsive disorder. In one embodiment, a method involves administering to the individual an effective amount of a selective CYP26B inhibitor, the selective CYP26B inhibitor having at least 10-fold selectivity for CYP26B relative to CYP26A. In another embodiment, a method involves administering to the individual an effective amount of a selective CYP26A inhibitor, the selective CYP26A inhibitor having a chemical formula set forth in the specification. The invention further provides screening methods for identifying a selective CYP26A inhibitor or selective CYP26B inhibitor.

  本发明提供了一种治疗患有视黄酸反应性障碍的个体的方法。在一个实施例中，一种方法包括向个体施用有效量的选择性CYP26B抑制剂，所述选择性CYP26B抑制剂相对于CYP26A至少具有10倍的选择性。在另一个实施例中，一种方法包括向个体施用有效量的选择性CYP26A抑制剂，所述选择性CYP26A抑制剂的化学公式如说明书所述。本发明还提供了用于识别选择性CYP26A抑制剂或选择性CYP26B抑制剂的筛选方法。
• CALCIUM-SENSING RECEPTOR-ACTIVE COMPOUNDS
  申请人：Fenscholdt Jef

  公开号：US20120101039A1

  公开（公告）日：2012-04-26

  A compound of general formula I their use as calcium receptor-active compounds for the prophylaxis, treatment or amelioration of physiological disorders or diseases associated with disturbances of CaSR activity, such as hyperparathyroidism, pharmaceutical compositions comprising said compounds, methods of treating diseases with said compounds, and the use of said compounds in the manufacture of medicaments.

  一种通用化学式I的化合物，其用作钙受体活性化合物，用于预防、治疗或改善与CaSR活性紊乱相关的生理紊乱或疾病，如甲状旁腺功能亢进症，包括所述化合物的药物组合物，使用所述化合物治疗疾病的方法，以及所述化合物用于制造药物。
• SUBSTITUTED BICYCLIC HETEROARYL COMPOUNDS AS RXR AGONISTS
  申请人：CONNEXIOS LIFE SCIENCES PVT. LTD.

  公开号：US20160333004A1

  公开（公告）日：2016-11-17

  The present invention relates to certain substituted bicyclic compounds that are agonists of RXR and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders.

  本发明涉及某些替代的双环化合物，它们是RXR的激动剂，因此在预防或治疗可以通过激活该受体来预防或治疗的某些疾病的治疗中有用。此外，本发明涉及这些化合物、其制备方法、含有这些化合物的药物组合物以及这些化合物在治疗某些疾病中的用途。
• Electrochemical Proton Reduction over Nickel Foam for <i>Z</i> ‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
  作者：Alejandro Valiente、Pablo Martínez‐Pardo、Gurpreet Kaur、Magnus J. Johansson、Belén Martín‐Matute

  DOI：10.1002/cssc.202102221

  日期：2022.1.10

  Foam catalyst: Commercially available nickel foam is an excellent catalyst for the electrochemical semihydrogenation/semideuteration of functionalized alkynes in diluted sulfuric acid under ambient conditions. Here, the applicability of this catalyst for the stereoselective synthesis of Z-alkenes and Z-alkenes-d2 is presented. The nickel foam is recyclable up to 14 times without losing its catalytic

  泡沫催化剂：市售的泡沫镍是在环境条件下稀硫酸中功能化炔烃的电化学半氢化/半氘化的优良催化剂。本文介绍了该催化剂在立体选择性合成Z-烯烃和Z-烯烃-d 2中的适用性。泡沫镍可回收多达 14 次，而不会失去其催化性能。