4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride | 139681-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride
• 英文别名: 4-pivaloylbenzoyl chloride；Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-；4-(2,2-dimethylpropanoyl)benzoyl chloride
• CAS: 139681-39-3
• 化学式: C₁₂H₁₃ClO₂
• 分子量: 224.687
• InChiKey: XQIWRUXPIFGECB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride 在 ammonium hydroxide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以90%的产率得到4-(2,2-dimethyl-1-oxopropyl)-benzamide
  参考文献：
  名称：

  Hypoglycemic Prodrugs of 4-(2,2-Dimethyl-1-oxopropyl)benzoic Acid

  摘要：

  SAH 51-641 (1) is a potent hypoglycemic agent, which acts by inhibiting hepatic gluconeogenesis. It is a prodrug of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid (2) and 4-(2,2-dimethyl-1-hydroxy propyl)benzoic acid (3), which sequester coenzyme A (CoA) in the mitochondria, and inhibits medium-chain acyltransferase. 1-3 and 4-tert-butylbenzoic acid all cause testicular degeneration in rats at pharmacologically active doses. 14b (FOX 988) is a prodrug of 3, which is metabolized in the liver at a rate sufficient enough to have hypoglycemic potency (an ED50 of 65 mu mol/kg, 28 mg/kg/day, for glucose lowering), yet by avoiding significant escape of the metabolite 3 to the systemic circulation, it avoids the testicular toxicity at doses up to 1500 mu mol/kg/day. 14b was selected for clinical studies.

  DOI：

  10.1021/jm980438y
• 作为产物：
  描述：

  2,2-二甲基-1-(4-甲基苯基)丙-1-酮 在 potassium permanganate 、 氯化亚砜 作用下， 反应 5.5h， 生成 4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride
  参考文献：
  名称：

  Hypoglycemic Prodrugs of 4-(2,2-Dimethyl-1-oxopropyl)benzoic Acid

  摘要：

  SAH 51-641 (1) is a potent hypoglycemic agent, which acts by inhibiting hepatic gluconeogenesis. It is a prodrug of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid (2) and 4-(2,2-dimethyl-1-hydroxy propyl)benzoic acid (3), which sequester coenzyme A (CoA) in the mitochondria, and inhibits medium-chain acyltransferase. 1-3 and 4-tert-butylbenzoic acid all cause testicular degeneration in rats at pharmacologically active doses. 14b (FOX 988) is a prodrug of 3, which is metabolized in the liver at a rate sufficient enough to have hypoglycemic potency (an ED50 of 65 mu mol/kg, 28 mg/kg/day, for glucose lowering), yet by avoiding significant escape of the metabolite 3 to the systemic circulation, it avoids the testicular toxicity at doses up to 1500 mu mol/kg/day. 14b was selected for clinical studies.

  DOI：

  10.1021/jm980438y
• 作为试剂：
  描述：

  4-(2,2-dimethyl-1-oxopropyl)-N-methoxybenzamide 、 4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride 在 4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride 作用下， 生成 ((Z)-C-(4-(2,2-Dimethylpropanoyl)phenyl)-N-methoxycarbonimidoyl)4-(2,2-dimethylpropanoyl)benzoate
  参考文献：
  名称：

  Process for preparing substituted N-oxy-imidic acid derivatives

  摘要：

  化学式为##STR1##的N-氧代取代的咪唑酸衍生物，其中R.sub.1、R.sub.2和R.sub.3是烷基和芳基取代基，可用作抗糖尿病和降脂药物，制备方法如下：##STR2##其中X为氯、溴或碘，R.sub.1'与R.sub.1相同，但任何羟基或羧基取代基都被羟基或羧基保护基保护，当R.sub.1'是保护的羟基或羧基取代基时，脱保护取代基。

  公开号：

  US05319123A1

文献信息

• Reduction in Glucose Levels in STZ Diabetic Rats by 4-(2,2-Dimethyl-1-oxopropyl)benzoic Acid:  A Prodrug Approach for Targeting the Liver
  作者：Gregory R. Bebernitz、Jeremy G. Dain、Rhonda O. Deems、Dario A. Otero、W. Ronald Simpson、Robert J. Strohschein

  DOI：10.1021/jm000264w

  日期：2001.2.1

  attempts at lowering glucose levels in vivo with 1 have been associated with toxicity in other organs such as the testes. An approach was developed utilizing the natural processing of triglyceride-like intermediates as a basis for selectively targeting the absorption, processing, and delivery of a prodrug to the liver. Compounds were identified by this method which lowered glucose levels in vivo without

  NIDDM患者肝脏中葡萄糖的过量产生显着地导致了他们的空腹高血糖，并且是脂肪细胞释放的过量游离脂肪酸（FFA）氧化增加的直接结果。先前已证明2-（1,1-二甲基乙基）-2-（4-甲基苯基）[1,3]二氧戊环（SAH51-641，1）可通过减少脂肪酸氧化从而降低糖尿病动物模型中的葡萄糖水平，因此剥夺了系统糖异生所必需的能量和辅因子。但是，尝试用1降低体内葡萄糖水平与其他器官（如睾丸）的毒性有关。已经开发出一种方法，该方法利用甘油三酸酯样中间体的天然加工作为选择性地将前药吸收，加工和递送至肝脏的基础。
• Benzoic acid derivatives as antidiabetic agents
  申请人：Sandoz Ltd.

  公开号：US05378728A1

  公开（公告）日：1995-01-03

  Compound of the formula ##STR1## where R is CH.sub.3 (CH.sub.2).sub.m, A and B are hydrogen, a bond or --(CH.sub.2).sub.n, X is ##STR2## m is 0, 1 , 2 or 3, n is 1 , 2, or 3, R.sub.1 is hydrogen or lower alkyl, and Y is --OH, --OR.sub.2 or --NR.sub.3 R.sub.4 where R.sub.2, R.sub.3 and R.sub.4 are hydrogen or unsubstituted or substituted alkyl, aryl and aralkyl substituents.

  化合物的公式为##STR1##其中R为CH.sub.3(CH.sub.2).sub.m，A和B为氢、一个键或--(CH.sub.2).sub.n，X为##STR2##m为0、1、2或3，n为1、2或3，R.sub.1为氢或较低的烷基，Y为--OH、--OR.sub.2或--NR.sub.3R.sub.4，其中R.sub.2、R.sub.3和R.sub.4为氢或未取代或取代的烷基、芳基和芳基烷基取代基。
• N-oxyimidic acid derivatives
  申请人：SANDOZ LTD.

  公开号：EP0463989B1

  公开（公告）日：1994-12-28
• US5319123A
  申请人：——

  公开号：US5319123A

  公开（公告）日：1994-06-07
• US5378728A
  申请人：——

  公开号：US5378728A

  公开（公告）日：1995-01-03