2-(3,5-二叔丁基-4-羟基亚苄基)丙二酸二乙酯 | 22014-02-4

• 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
• 中文名称: 2-(3,5-二叔丁基-4-羟基亚苄基)丙二酸二乙酯
• 英文名称: diethyl 2-(3,5-di-tert-butyl-4-hydroxybenzylidene)malonate
• 英文别名: (3,5-di-tert-butyl-4-hydroxy-benzylidene)-malonic acid diethyl ester；(3,5-Di-tert-butyl-4-hydroxy-benzyliden)-malonsaeure-diaethylester；2-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-malonic acid diethyl ester；Diethyl 2-(3,5-di-t-butyl-4-hydroxybenzylidene)malonate；diethyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]propanedioate
• CAS: 22014-02-4
• 化学式: C₂₂H₃₂O₅
• 分子量: 376.493
• InChiKey: CZCRNTZQHFDOBY-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C(Solv: ethanol (64-17-5))
• 沸点：
  421.2±40.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙二酸二乙酯 、 3,5-二叔丁基-4-羟基苯甲醛 在 哌啶 作用下， 以 吡啶 为溶剂， 反应 1.5h， 以67%的产率得到2-(3,5-二叔丁基-4-羟基亚苄基)丙二酸二乙酯
  参考文献：
  名称：

  Anionic condensations of 3,5-di-tert-butyl-4(2)-hydroxybenzaldehydes in the presence of weak bases

  摘要：

  Products of the reactions of 4- and 2-hydroxy-3,5-di-tert-butyl-benzaldehydes with malonic acid, diethyl malonate, and acetic anhydride in the presence of weak bases were isolated and identified. The reactions of 3,5-di-tert-butyl-4-hydroxybenzaldehyde with malonic acid and acetic anhydride in the presence of sodium acetate and piperidine gave 3,5-di-tert-butyl-4-hydroxycinnamic acid. The reaction of its 2-hydroxy isomer with acetic anhydride stopped at the stage of formation of the corresponding O-acetyl derivative, while in the reaction with malonic acid the corresponding substituted cinnamic acid and its lactone (coumarin derivative) were formed as intermediate products in a transformation sequence finally leading to 3-(3,5-di-tertbutyl-2-hydroxyphenyl)-3-piperidinopropionic acid and 6,8-di-tert-butyl-2-oxo-3,4-dihydro-2H-chromen-4-ylacetic acid. Analogous differences were typical of reactions of isomeric 4- and 2-hydroxy-3,5-di-tert-butylbenzaldehydes with diethyl malonate. The transformations of the 2-hydroxy isomer were accompanied by hydrolysis and formation of an adduct of intermediate coumarin derivative with diethyl malonate and piperidine.

  DOI：

  10.1134/s1070428008060043

文献信息

• Chemical uncouplers for the treatment of obesity
  申请人：——

  公开号：US20040138301A1

  公开（公告）日：2004-07-15

  This invention relates to chemical uncouplers with a broader safety window making the use of them in treating obesity and, consequently, in the treatment of obesity related diseases and conditions such as atherosclerosis, hypertension, diabetes, especially type 2 diabetes (NIDDM (non-insulin dependent diabetes mellitus)), impaired glucose tolerance, dyslipidemia, coronary heart disease, gallbladder disease, osteoarthritis and various types of cancer such as endometrial, breast, prostate and colon cancers and the risk for premature death as well as other conditions, such as diseases and disorders, which conditions are improved by an increase in mitochondrial respiration, more attractive.

  这项发明涉及一种化学解偶联剂，它具有更宽的安全窗口，使其在治疗肥胖症以及因此引发的相关疾病和状况，如动脉硬化、高血压、糖尿病（尤其是2型糖尿病（非胰岛素依赖型糖尿病））、葡萄糖耐量受损、血脂异常、冠心病、胆结石病、骨关节炎以及子宫内膜、乳房、前列腺和结肠等各种癌症以及过早死亡的风险等方面更具吸引力。此外，还包括其他通过增加线粒体呼吸得到改善的条件、疾病和紊乱。
• Methods and compositions for treating obesity, preventing weight gain, promoting weight loss, promoting slimming, or treating or preventing the development of diabetes
  申请人：NAN Global, LLC

  公开号：US10849872B2

  公开（公告）日：2020-12-01

  The present invention relates to compositions and kits including a chemical uncoupler, such as tyrphostin 9 or precursor or a salt thereof, and compositions including a chemical uncoupler, such as tyrphostin 9 in combination with one or more therapeutic agents, for example, L-carnitine, which are useful, for example, in treating obesity, preventing weight gain, promoting weight loss/slimming, and/or treating or preventing the development of diabetes.

  本发明涉及包括化学解偶联剂的组合物和试剂盒，如tyrphostin 9或其前体或盐，以及包括化学解偶联剂的组合物，如tyrphostin 9与一种或多种治疗剂（例如左旋肉碱）的组合物，这些组合物在治疗肥胖症、防止体重增加、促进减肥/瘦身和/或治疗或预防糖尿病发展等方面有用。
• Katsumi; Kondo; Fuse, Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 4, p. 1619 - 1627
  作者：Katsumi、Kondo、Fuse、Yamashita、Hidaka、Hosoe、Takeo、Yamashita、Watanabe

  DOI：——

  日期：——
• Lauerer et al., Zeitschrift fur Physikalische Chemie (Leipzig), <N.F.> 10 <1957> 236, 262
  作者：Lauerer et al.

  DOI：——

  日期：——
• KATSUMI, IKUO;KONDO, HIDEO;FUSE, YOSHIHIDE;YAMASHITA, KATSUJI;HIDAKA, TAK+, CHEM. AND PHARM. BULL., 1986, 34, N 4, 1619-1627
  作者：KATSUMI, IKUO、KONDO, HIDEO、FUSE, YOSHIHIDE、YAMASHITA, KATSUJI、HIDAKA, TAK+

  DOI：——

  日期：——