methyl 4-(2,2-dimethyl-1-oxopropyl)benzoate | 220764-79-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(2,2-dimethyl-1-oxopropyl)benzoate
• 英文别名: methyl 4-pivaloylbenzoate；methyl 4-(2,2-dimethylpropanoyl)benzoate
• CAS: 220764-79-4
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: JMICZAIZGGETSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(2,2-dimethyl-1-oxopropyl)benzoate 在 氢氧化钾 、 dimethyl sulfide borane 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 4-[(1S)-1-hydroxy-2,2-dimethylpropyl]benzoic acid
  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 盐酸 、 potassium permanganate 作用下， 反应 7.0h， 生成 methyl 4-(2,2-dimethyl-1-oxopropyl)benzoate
  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

文献信息

• SUBSTITUTED HYDROXAMIC ACIDS AND USES THEREOF
  申请人：Blackburn Christopher

  公开号：US20110212969A1

  公开（公告）日：2011-09-01

  This invention provides compounds of formula (I): wherein ring A, X 1 , X 2 , X 3 , R 2 , R 4b , R 10 , and G have values as described in the specification, useful as inhibitors of HDAC6. The invention also provides pharmaceutical compositions comprising the compounds of the invention, and methods of using the compositions in the treatment of proliferative, inflammatory, infectious, neurological or cardiovascular diseases or disorders.

  这项发明提供了式（I）的化合物： 其中环A、X1、X2、X3、R2、R4b、R10和G的取值如规范中所述，可用作HDAC6的抑制剂。该发明还提供了包括该发明化合物的药物组合物，以及在治疗增殖性、炎症性、感染性、神经系统或心血管疾病或紊乱中使用该组合物的方法。
• Manganese-Catalyzed Aromatic C–H Allylation of Ketones
  作者：Shaukat Ali、Jiaqi Huo、Congyang Wang

  DOI：10.1021/acs.orglett.9b02554

  日期：2019.9.6

  Manganese-catalyzed aromatic C-H allylation of ketones is reported. The reaction proceeded in a monoselective allylation manner to provide various ortho C-H allylated ketones in high yields. With challenging allylic electrophiles bearing substituents at the α-, β-, or γ-position, excellent SN2' regioselectivity was achieved under mild conditions (rt to 35 °C). Mechanistic studies revealed a possible

  报道了锰催化的酮的芳族CH烯丙基化。反应以单选择烯丙基化方式进行，以高产率提供各种邻位CH烯丙基化酮。通过在α-，β-或γ-位置带有取代基的具有挑战性的烯丙基亲电试剂，在温和条件下（室温至35°C）可获得出色的SN2'区域选择性。机理研究表明，可能的限制营业额的CH键裂解步骤提供了五元Manganacycle，然后与烯丙基亲电试剂反应生成CH烯丙基化产物。
• Copper-Catalyzed Hydrosilylation with a Bowl-Shaped Phosphane Ligand: Preferential Reduction of a Bulky Ketone in the Presence of an Aldehyde
  作者：Tetsuaki Fujihara、Kazuhiko Semba、Jun Terao、Yasushi Tsuji

  DOI：10.1002/anie.200906348

  日期：2010.2.15

  Hollywood bowl: A highly active copper catalyst with a bowl‐shaped phosphane (bsp) ligand was used in the hydrosilylation reaction of bulky ketones. The preferential reduction of a bulky ketone in the presence of an unprotected aldehyde is unprecedented.

  好莱坞碗（Hollywood Bowl）：具有大碗状膦（bsp）配体的高活性铜催化剂被用于大体积酮的氢化硅烷化反应。在未保护的醛存在下优先还原大体积的酮是前所未有的。
• CONFORMATIONALLY RESTRICTED UREA INHIBITORS OF SOLUBLE EPOXIDE HYDROLASE
  申请人：Hammock D. Bruce

  公开号：US20070225283A1

  公开（公告）日：2007-09-27

  Inhibitors of the soluble epoxide hydrolase (sEH) are provided that incorporate multiple pharmacophores and are useful in the treatment of diseases.

  提供了可抑制可溶性环氧化物水解酶（sEH）的抑制剂，这些抑制剂结合了多种药效团，并且在治疗疾病方面具有用途。
• Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkyl Amides
  作者：Chang-An Wang、Md. Mahbubur Rahman、Elwira Bisz、Błażej Dziuk、Roman Szostak、Michal Szostak

  DOI：10.1021/acscatal.1c05738

  日期：2022.2.18

  Pd-catalyzed Suzuki–Miyaura cross-coupling of aliphatic amides. Although tremendous advances have been made in the cross-coupling of aromatic amides, C–C bond formation from aliphatic amides by selective N–C(O) cleavage has remained a major challenge. This longstanding problem in Pd catalysis has been addressed herein by a combination of (1) the discovery of N,N-pym/Boc amides as a class of readily accessible

  我们报告了 Pd 催化的脂肪族酰胺的 Suzuki-Miyaura 交叉偶联。尽管在芳香酰胺的交叉偶联方面取得了巨大进展，但脂肪族酰胺的 C-C 键形成通过选择性 N-C(O) 裂解产生的酰胺仍然是一个重大挑战。Pd 催化中这一长期存在的问题已通过以下组合得到解决： (1) 发现 N,N-pym/Boc 酰胺作为一类易于获得的用于交叉偶联的酰胺基试剂和 (2) 孔的空间调节-定义的用于交叉偶联的 Pd(II)-NHC 催化剂。该方法对于 3°、2° 和 1° 脂肪族酰胺衍生物阵列的交叉偶联是有效的。该催化剂系统对用户友好，因为催化剂很容易获得并且对空气和工作台稳定。机理研究强烈支持酰胺键扭曲和外部 n N → π* C=O/Ar离域作为 N,N-pym/Boc 酰胺在选择性 N-C(O) 键活化中的统一使能特征。该方法提供了一个罕见的 Pd-NHC 催化的脂肪族酰基酰胺亲电试剂交叉偶联的例子。