(1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐 | 229613-83-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐
• 英文名称: (-)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
• 英文别名: (1S,4R)-Methyl 4-aminocyclopent-2-enecarboxylate hydrochloride；methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate;hydrochloride
• CAS: 229613-83-6
• 化学式: C₇H₁₁NO₂*ClH
• 分子量: 177.631
• InChiKey: SWYRZYIXFKDJEK-IBTYICNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  2-8°C

制备方法与用途

简介

(1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐应称为(1S, 4R)-(-)-甲基-4-氨基环戊-2-烯-1-甲酸酯盐酸盐，可通过将(-)-(1R,4S)-2-氮杂双环[2.2.1]庚-5-烯-3-酮用盐酸加热开环得到。有文献报道该化合物可用于制备具有3-苯基异噁唑啉-5-羧酰胺结构的除草剂。

制备

将(-)-(1R,4S)-2-氮杂双环[2.2.1]庚-5-烯-3-酮（83，3.0g，27.5mmol）和1.25M HCl在MeOH（59.0mL，73.8mmol）中的混合物加热回流12小时。将反应混合物在减压下浓缩，并与Et₂O（42mL）搅拌。收集获得的固体，用Et₂O洗涤，并在真空中干燥，最终得到4.2g (85%) 的(1S, 4R)-(-)-甲基-4-氨基环戊-2-烯-1-甲酸酯盐酸盐（84）。

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐 在 palladium on activated charcoal sodium azide 、 甲烷磺酸 、 氢气 、 三乙胺 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 48.83h， 生成 (1S,3R)-1-(9-adenenyl)-3-methylcarboxycyclopentane
  参考文献：
  名称：

  Metal Coordination-Based Inhibitors of Adenylyl Cyclase:  Novel Potent P-Site Antagonists

  摘要：

  The adenylyl cyclases (ACS) are a family of intracellular enzymes associated with signal transduction by virtue of their ability to convert ATP to cAMP. The catalytic mechanism of this transformation proceeds through initial binding of ATP to the so-called purine binding site (P-site) of the enzyme followed by metal-mediated cyclization with loss of pyrophosphate. Crystallographic analysis of ACs with known inhibitors reveals the presence of two metals in the active site. Presently, nine isoforms of adenylyl cyclase are known, and unique isoform combinations are expressed in a tissue-specific manner. The development of isoform-specific inhibitors of adenylyl cyclase may prove to be a useful strategy toward the design of unique signal transduction inhibitors. To develop novel AC inhibitors, we have chosen an approach to inhibitor design utilizing an adenine ring system joined to a metal-coordinating hydroxamic acid via various linkers. Previous work in our group has validated this approach and identified novel inhibitors that possess an adenine ring joined to a metal-coordinating hydroxamic acid through flexible acyclic linkers (Levy, D. E., et al. Bioorg. Med. Chem. Lett. 2002, 12, 30853088). Subsequent studies have focused on the introduction of conformational restrictions into the tether of the inhibitors with the goal of increasing potency (Levy, D. E., et al. Bioorg. Med. Chem. Lett. 2002, 12, 3089-3092). Building upon the favorable spatial positioning of the adenine and hydroxamate groups coupled with potentially favorable entropic factors, the unit joining the carbocycle to the hydroxamate was explored further and a stereochemical-based SAR was elucidated, leading to a new series of highly potent AC inhibitors.

  DOI：

  10.1021/jm0205604
• 作为产物：
  描述：

  2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 盐酸 作用下， 以 甲醇 为溶剂， 以94.9%的产率得到(1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐
  参考文献：
  名称：

  EP1334969

  摘要：

  公开号：

文献信息

• ENHANCED ANTI-INFLUENZA AGENTS CONJUGATED WITH ANTI-INFLAMMATORY ACTIVITY
  申请人：ACADEMIA SINICA

  公开号：US20130274229A1

  公开（公告）日：2013-10-17

  Novel dual-targeted, bifunctional anti-influenza drugs formed by conjugation with anti-inflammatory agents are disclosed. Exemplary drugs according to the invention include caffeic acid (CA)-bearing zanamivir (ZA) conjugates ZA-7-CA (1), ZA-7-CA-amide (7) and ZA-7-Nap (43) for simultaneous inhibition of influenza virus neuraminidase and suppression of proinflammatory cytokines. Synthetic methods for preparation of these enhanced anti-influenza conjugate drugs are provided. The synthetic bifunctional ZA conjugates act synergistically towards protection of mice lethally infected by H1N1 or H5N1 influenza viruses. The efficacy of ZA-7-CA, ZA-7-CA-amide and ZA-7-Nap conjugates is much greater than the combination therapy of ZA with anti-inflammatory agents.

  新型双靶向、双功能抗流感药物通过与抗炎药物结合形成。根据本发明的示例药物包括咖啡酸（CA）基底的扎那米韦（ZA）共轭物ZA-7-CA（1）、ZA-7-CA酰胺（7）和ZA-7-Nap（43），用于同时抑制流感病毒神经氨基酸酶和抑制促炎细胞因子。提供了用于制备这些增强型抗流感共轭药物的合成方法。合成的双功能ZA共轭物对保护由H1N1或H5N1流感病毒致命感染的小鼠具有协同作用。ZA-7-CA、ZA-7-CA酰胺和ZA-7-Nap共轭物的疗效远远优于ZA与抗炎药物的联合治疗。
• [EN] 4, 7-DIAZAINDOLE AND 4, 7-DIAZAINDAZOLE DERIVATIVES AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA<br/>[FR] DÉRIVÉS DE 4,7-DIAZAINDOLE ET 4,7-DIAZAINDAZOLE ET LEUR UTILISATION POUR TRAITER OU PRÉVENIR LA GRIPPE, OU POUR ATTÉNUER SES SYMPTÔMES
  申请人：SAVIRA PHARMACEUTICALS GMBH

  公开号：WO2017133658A1

  公开（公告）日：2017-08-10

  The present invention relates to a compound having the formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameloriating or preventing influenza.

  本发明涉及具有式(I)的化合物，可选地以药学上可接受的盐、溶剂合物、多型体、前药、共药、共晶体、互变异构体、拉克酸盐、对映体或非对映体或其混合物的形式存在，该化合物在治疗、改善或预防流感方面具有用处。
• [EN] PYRIMIDINE AND PYRIDINE DERIVATIVES AND USE IN TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA THEREOF<br/>[FR] DÉRIVÉS DE PYRIMIDINE ET DE PYRIDINE ET LEUR UTILISATION POUR TRAITER OU PRÉVENIR LA GRIPPE, OU POUR ATTÉNUER SES SYMPTÔMES
  申请人：SAVIRA PHARMACEUTICALS GMBH

  公开号：WO2017133667A1

  公开（公告）日：2017-08-10

  Provided herein is a compound of formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing influenza.

  本文提供的是一种化合物，其化学式为（I），可以是药用盐、溶剂合物、多型体、前药、共药、共晶、互变异构体、消旋体、对映体或二对映体，或它们的混合物形式，该化合物在治疗、改善或预防流感方面具有用处。
• Synthesis of N−H Bearing Imidazolidinones and Dihydroimidazolones Using Aza‐Heck Cyclizations
  作者：Feiyang Xu、Scott A. Shuler、Donald A. Watson

  DOI：10.1002/anie.201806295

  日期：2018.9.10

  The synthesis of unsaturated, unprotected imidazolidinones via an aza‐Heck reaction is described. This palladium‐catalyzed process allows for the cyclization of N‐phenoxy ureas onto pendant alkenes. The reaction has broad functional group tolerance, can be applied to complex ring topologies, and can be used to directly prepare mono‐ and bis‐unprotected imidazolidinones. By addition of Bu4NI, dihydroimidazolones

  描述了通过氮杂赫克反应合成不饱和、未保护的咪唑啉酮。这种钯催化的过程允许N-苯氧基脲环化到侧链烯烃上。该反应具有广泛的官能团耐受性，可应用于复杂的环拓扑，并可用于直接制备单和双未保护的咪唑啉酮。通过添加Bu 4 NI，可以从相同的起始材料获得二氢咪唑酮。还报道了制备不饱和、未保护的内酰胺的改进条件。
• [EN] CONDENSED ISOXAZOLINE DERIVATIVES AND THEIR USE AS HERBICIDES<br/>[FR] DÉRIVÉS D'ISOXAZOLINE CONDENSÉS ET LEUR UTILISATION COMME HERBICIDES
  申请人：BASF SE

  公开号：WO2021224040A1

  公开（公告）日：2021-11-11

  The invention relates to compounds of formula (I), and their use as herbicides. In said formula, R1 to R6 represent groups such as hydrogen, halo-gen or organic groups such as alkyl, alkenyl, alkynyl, or alkoxy; W is a bicyclic heterocycle; X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxyl or a linear or cyclic organic group. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

  该发明涉及公式（I）的化合物，以及它们作为除草剂的用途。在该公式中，R1到R6代表诸如氢、卤素或有机基团（如烷基、烯基、炔基或烷氧基）等基团；W是一个双环杂环；X是一个键或二价基团；Y是氢、氰基、羟基或线性或环状有机基团。该发明还涉及包含这种化合物的组合物以及将其用于控制不受欢迎的植被。