5-(chloromethyl)-2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione | 109885-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(chloromethyl)-2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione
• 英文别名: 2-chloromethyl-3,5,6-trimethyl-[1,4]benzoquinone；2-chloromethyl-3,5,6-trimethylbenzoquinone；2-(chloromethyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
• CAS: 109885-41-8
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: WLYDZHCJSPHCFM-UHFFFAOYSA-N

物化性质

• 沸点：
  265.5±19.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(chloromethyl)-2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione 、 2-硝基丙酸乙酯 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以65%的产率得到2-Methyl-2-nitro-3-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Cαα-unsymmetrically disubstituted nitroesters by electron transfer C-alkylation of ethyl 2-nitropropionate anion

  摘要：

  The ethyl 2-nitropropionate anion was shown to react with six reductive alkylating agents to give new C-alpha alpha-unsymmctrically disubstituted nitroesters and in some cases new ethyl monosubstituted methacrylates. The C-alkylation was shown to proceed by the S(RN)1 mechanism which was confirmed by the classical criteria for S(RN)1 reaction: the electron-withdrawing group effect and classical inhibition experiments by dioxygen, p-dinitrobenzene, cupric chloride or TEMPO. For example, ethyl 2-methyl-2-nitro-3-p-nitrophenylpropionate was transformed in the corresponding amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00194-x
• 作为产物：
  描述：

  三甲基氢醌 在 sodium tetrahydroborate 、 氯化亚砜 、 ammonium cerium(IV) nitrate 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 生成 5-(chloromethyl)-2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  四取代的1,4-苯醌的S RN 1反应

  摘要：

  通过S RN 1机理显示2-氯甲基-3,5,6-三甲基-1,4-苯醌的2-氯甲基-C-烷基化反应是通过S RN 1机理进行的。该机理被双氧，对二硝基苯，氯化铜和二叔丁基硝基氧的抑制作用所证实。首次发现由双氧诱导的硝基和亚硝酸盐衍生物的形成。

  DOI：

  10.1016/s0040-4039(00)79881-9

文献信息

• New Drug Delivery System for Crossing the Blood Brain Barrier
  申请人：Lipshutz H. Bruce

  公开号：US20070203080A1

  公开（公告）日：2007-08-30

  New ubiquinol analogs are disclosed, as well as methods of using these compounds to deliver drug moieties to the body.

  新的泛醌类似物被披露，以及利用这些化合物将药物基团输送到人体的方法。
• An expeditious route to CoQn, vitamins K1 and K2, and related allylated para-quinones utilizing Ni(0) catalysis
  作者：Bruce H. Lipshutz、Sung-kyu Kim、Paul Mollard、Kirk L. Stevens

  DOI：10.1016/s0040-4020(97)10222-8

  日期：1998.2

  Coupling reactions between vinylalanes and chloromethylated para-quinones, mediated by catalytic amounts of Ni(0), lead directly to allylated products, including coenzyme Q, and vitamins K1 and K2.

  催化量的Ni（0）介导的乙烯基丙氨酸与氯甲基化对醌之间的偶联反应直接导致烯丙基化产物，包括辅酶Q以及维生素K 1和K 2。
• Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
  申请人：Miller M. Guy

  公开号：US20060281809A1

  公开（公告）日：2006-12-14

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  披露了治疗或抑制线粒体疾病的方法，如弗里德赖希共济失调（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、卒中（MELAS）或科恩斯-赛尔综合征（KSS），以及在本发明方法中有用的化合物，如α-生育酚醌。还披露了用于治疗其他疾病的方法和化合物。还披露了用于评估受试者代谢状态和治疗效果的能量生物标志物。还披露了调节、正常化或增强能量生物标志物的方法，以及用于这些方法的化合物。
• Side-chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
  申请人：Miller M. Guy

  公开号：US20070225261A1

  公开（公告）日：2007-09-27

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  本发明揭示了治疗或抑制线粒体疾病的方法，例如弗里德雷希共济失调症（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、中风（MELAS）或克恩斯-萨耶综合征（KSS），以及在该方法中有用的化合物。还揭示了用于治疗其他疾病的方法和化合物。还揭示了有用于评估受试者代谢状态和治疗效果的能量生物标志物。还揭示了调节、规范或增强能量生物标志物的方法，以及用于此类方法的化合物。
• Quinone derivatives
  申请人：Shionogi BioResearch Corporation

  公开号：US06433199B1

  公开（公告）日：2002-08-13

  The invention relates to a quinone derivative of the following formula: which is capable of converting into two alkylating agents upon bioreduction. Substituents A, B, C, and D are as described herein.

  该发明涉及以下式的醌衍生物：该衍生物在生物还原作用下能够转化为两种烷基化剂。取代基A、B、C和D如本文所述。