3-methoxy-5-oxo-cyclohex-3-ene-1-carboxylic acid | 95298-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-5-oxo-cyclohex-3-ene-1-carboxylic acid
• 英文别名: 3-methoxy-5-oxocyclohex-3-9-ene carboxylic acid；3-Methoxy-5-oxocyclohex-3-ene-1-carboxylic acid
• CAS: 95298-68-3
• 化学式: C₈H₁₀O₄
• mdl: MFCD09910114
• 分子量: 170.165
• InChiKey: BKHQMEKQAGIFLU-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• 沸点：
  385.5±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-5-oxo-cyclohex-3-ene-1-carboxylic acid 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  用于检测半胱氨酸氧化的三功能钒（IV）配合物

  摘要：

  开发有效的分子探针以检测和成像细胞中氧化应激的水平仍然是一个挑战。本文中，我们报告了一种新型光学探针的设计，合成和初步生物学评估，该探针可监测基于半胱氨​​酸的磷酸酶（CBPs）中硫醇基的氧化。遵循正交保护方法，我们合成了旨在结合CBP的新的钒基复合物。该复合物可以通过众所周知的二甲酮衍生物（共价捕获亚磺酸，SOH）和基于香豆素的荧光团进行功能​​化，以进行光学可视化。我们表明，这种新探针在体外可有效结合一系列磷酸酶具有纳摩尔亲和力。此外，对活HCT116细胞的初步流式细胞术和显微镜研究表明，该探针可以成功地对细胞中的亚硫酸水平进行成像，其中亚硫酸是蛋白质氧化损伤的结果之一。

  DOI：

  10.1039/c7dt00076f
• 作为产物：
  描述：

  1,4-dihydro-3,5-dimethoxybenzoic acid 在 盐酸 作用下， 生成 3-methoxy-5-oxo-cyclohex-3-ene-1-carboxylic acid
  参考文献：
  名称：

  The Reduction of Aromatic Acids and Amides by Sodium in Liquid Ammonia

  摘要：

  DOI：

  10.1021/ja01525a042

文献信息

• COMPOUND USED AS AUTOPHAGY REGULATOR, AND PREPARATION METHOD THEREFOR AND USES THEREOF
  申请人：WIGEN BIOMEDICINE TECHNOLOGY (SHANGHAI) CO., LTD.

  公开号：US20200190066A1

  公开（公告）日：2020-06-18

  It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.

  该内容涉及作为自噬调节剂的化合物及其制备和使用方法，具体提供了一类具有通用公式(I)的化合物，或其药用可接受盐，这是一种自噬调节剂，特别是哺乳动物ATG8同源物调节剂。
• Cyclohexanediones and their use as plant growth regulators
  申请人：Ciba-Geigy Corporation

  公开号：US04872902A1

  公开（公告）日：1989-10-10

  The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl, A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4, R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl, R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5, R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl, R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical, B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.4 -alkylsulphonyl, R.sub.6 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, and R.sub.7 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -haloalkenyl or C.sub.3 -C.sub.6 -alkynyl, and to salts of the compounds of formula I with acids, bases or complex-formers, to processes for the preparation thereof and to novel intermediates. The compounds of formula I have herbicidal and growth-regulating action.

  该发明涉及具有以下结构的新型环己二酮化合物：其中R为氢或C.sub.1 -C.sub.6 -烷基，A为R.sub.2、OR.sub.3或NR.sub.3 R.sub.4，R.sub.2为未取代或经C.sub.1 -C.sub.4 -甲氧基单取代或多取代卤素的C.sub.1 -C.sub.6 -烷基，或为C.sub.3 -C.sub.6 -环烷基，R.sub.3为C.sub.1 -C.sub.6 -烷基或C.sub.3 -C.sub.6 -环烷基，或为未取代或经R.sub.5单取代、双取代或三取代的苯基或苄基，R.sub.4为氢、C.sub.1 -C.sub.6 -烷基、C.sub.1 -C.sub.4 -甲氧基或C.sub.3 -C.sub.6 -环烷基，R.sub.3和R.sub.4与它们结合的氮原子一起，是吡咯烷、吗啉或哌啶基团，B为以下基团之一，m为0、1、2或3，R.sub.5为卤素、硝基、氰基、C.sub.1 -C.sub.4 -烷基、C.sub.1 -C.sub.4 -甲氧基、C.sub.1 -C.sub.4 -烷基硫、C.sub.1 -C.sub.4 -卤代烷基、C.sub.1 -C.sub.4 -烷基砜基或C.sub.1 -C.sub.4 -烷基磺酰基，R.sub.6为C.sub.1 -C.sub.6 -烷基或C.sub.3 -C.sub.6 -环烷基，R.sub.7为氢、C.sub.1 -C.sub.6 -烷基、C.sub.1 -C.sub.6 -卤代烷基、C.sub.3 -C.sub.6 -烯基、C.sub.3 -C.sub.6 -卤代烯基或C.sub.3 -C.sub.6 -炔基，以及具有上述结构的化合物与酸、碱或络合剂形成的盐、其制备方法和新的中间体。具有上述结构的化合物具有除草和生长调节作用。
• [EN] TARGETED COVALENT PROBES AND INHIBITORS OF PROTEINS CONTAINING REDOX-SENSITIVE CYSTEINES<br/>[FR] SONDES COVALENTES CIBLÉES ET INHIBITEURS DE PROTÉINES CONTENANT DES CYSTÉINES SENSIBLES À L'OXYDORÉDUCTION
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2014089546A1

  公开（公告）日：2014-06-12

  Covalent, irreversible small-molecule inhibitors that modify the sulfenyl form (i.e., sulfenic acid, RSOH and sulfenamide, RSNR'2) of therapeutically important proteins (particularly kinases and phosphatases) are disclosed, where the compositions include a compound having a substituted aryl or heterocyclic core structure that promotes binding interactions with a specific protein, and a nucleophilic reaction center (carbon, nitrogen, sulfur, or phosphorous) that is capable of forming a covalent bond with a sulfenic acid- or sulfenamide-modified cysteine residue in the protein. Methods for synthesizing these compounds are also disclosed, as well as methods of using them for determining the bioactivity of a chemical composition comprising an active compound toward a specific protein and for determining the potency of an inhibitor against a specific protein.

  揭示了用于修饰治疗重要蛋白质（特别是激酶和磷酸酶）的亚硫酰形式（即亚硫酸，RSOH和亚硫酰胺，RSNR'2）的共价、不可逆的小分子抑制剂，其中组合物包括具有取代芳基或杂环核结构的化合物，促进与特定蛋白质的结合相互作用，以及能够与蛋白质中的亚硫酸或亚硫酰胺修饰的半胱氨酸残基形成共价键的亲核反应中心（碳、氮、硫或磷）。还揭示了合成这些化合物的方法，以及使用它们确定包含活性化合物的化学组合物对特定蛋白质的生物活性以及确定抑制剂对特定蛋白质的效力的方法。
• Cyclohexanedionecarboxylic acid derivatives with herbicidal and plant
  申请人：Ciba-Geigy Corporation

  公开号：US04618360A1

  公开（公告）日：1986-10-21

  Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical, B is hydroxyl, an --NHOR.sub.1 radical or a metal or ammonium salt thereof R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkythio, R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl, R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.6 aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro or cyano, and R.sub.3 and R.sub.4, together with the nitrogen atom to which they are attached, also form a 5- or 6-membered heterocyclic ring system which may contain an additional oxygen or sulfur atom in the ring.

  新颖的环己二酮羧酸衍生物具有除草和植物生长调节性能。环己二酮羧酸衍生物具有以下化学式I ##STR1## 其中A是--OR.sub.2或--NR.sub.3 R.sub.4基团，B是羟基，--NHOR.sub.1基团或其金属或铵盐，R是C.sub.1-C.sub.6烷基或C.sub.3-C.sub.6环烷基，每个未取代或被卤素、C.sub.1-C.sub.6烷氧基或C.sub.2-C.sub.4烷硫基取代，R.sub.1是C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6卤代烷基、C.sub.3-C.sub.6烯基、C.sub.3-C.sub.6卤代烯基或C.sub.3-C.sub.6炔基，R.sub.2、R.sub.3和R.sub.4各自独立地是氢、C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6卤代烷基、C.sub.2-C.sub.10烷氧基烷基、C.sub.2-C.sub.10烷硫基烷基；C.sub.3-C.sub.6烯基，未取代或被卤素、C.sub.1-C.sub.4烷氧基或C.sub.1-C.sub.4烷硫基取代；C.sub.3-C.sub.6炔基；苯基或C.sub.1-C.sub.6芳基甲基，其中苯环未取代或被卤素、C.sub.1-C.sub.4烷基、C.sub.1-C.sub.4烷氧基、C.sub.1-C.sub.4卤代烷基、硝基或氰基取代，且R.sub.3和R.sub.4与它们连接的氮原子一起也形成一个含有额外氧或硫原子的5-或6元杂环系统。
• Redox-based probes as tools to monitor oxidized protein tyrosine phosphatases in living cells
  作者：Francisco J. Garcia、Kate S. Carroll

  DOI：10.1016/j.ejmech.2014.06.040

  日期：2014.12

  class of inhibitors for phosphatases. We envision a nucleophile reacting with the oxidized inactive catalytic cysteine to generate an irreversible thioether adduct which prevents the phosphatase from being reactivated and ultimately fortifies the signaling cascade. Our results reveal the potential of translation of our redox-based probes, which are used to understand redox cell circuitry and disease biology

  蛋白质酪氨酸磷酸酶 (PTP) 的可逆氧化已成为一种重要的调节机制，活性氧 (ROS) 通过该机制使 PTP 失活并促进信号级联的磷酸化和诱导。由于缺乏直接检测氧化 PTP 的灵敏且稳健的方法，因此很难理解 PTP 氧化失活在氧化还原信号传导中的作用。我们报告了使用基于氧化还原的探针在细胞环境中直接检测氧化 PTP，这突出了直接方法在帮助研究氧化还原调节中的生理和病理生理 PTP 活性方面​​的重要性。我们还证明，作为概念验证，这些基于氧化还原的探针可作为设计和开发一类新型磷酸酶抑制剂的原型。我们设想亲核试剂与氧化的无活性催化半胱氨酸反应生成不可逆的硫醚加合物，以防止磷酸酶被重新激活并最终加强信号级联。我们的结果揭示了我们的基于氧化还原的探针（用于了解氧化还原细胞电路和疾病生物学）转化为基于小分子亲核试剂的抑制剂的潜力，该抑制剂可治疗与氧化还原应激相关的疾病。这可能对 2 型糖尿病和癌症的