2-ethyl-3,3-dimethyl-butyryl chloride | 67632-27-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2-ethyl-3,3-dimethyl-butyryl chloride
• 英文别名: 2-Aethyl-3,3-dimethyl-butyrylchlorid；2-Ethyl-3,3-dimethylbutanoyl chloride
• CAS: 67632-27-3
• 化学式: C₈H₁₅ClO
• 分子量: 162.66
• InChiKey: KLSHSRMTFOMARP-UHFFFAOYSA-N

物化性质

• 沸点：
  67-69 °C(Press: 25 Torr)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethyl-3,3-dimethyl-butyryl chloride 在 4-二甲氨基吡啶 、 三氯溴甲烷 、 2-mercaptopyridine-1-oxide sodium salt 作用下， 反应 3.0h， 以82%的产率得到3-溴-2,2-二甲基-戊烷
  参考文献：
  名称：

  Stofer, Edmond; Lion, Claude, Bulletin des Societes Chimiques Belges, 1987, vol. 96, # 8, p. 623 - 628

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-Butylethylessigsaeure 在 氯化亚砜 作用下， 生成 2-ethyl-3,3-dimethyl-butyryl chloride
  参考文献：
  名称：

  Steric Effects in Hydrolysis of Hindered Amides and Nitriles¹

  摘要：

  DOI：

  10.1021/ja01567a046

文献信息

• Synthesis and Evaluation of Antiallodynic and Anticonvulsant Activity of Novel Amide and Urea Derivatives of Valproic Acid Analogues
  作者：Dan Kaufmann、Meir Bialer、Jakob Avi Shimshoni、Marshall Devor、Boris Yagen

  DOI：10.1021/jm901229s

  日期：2009.11.26

  Valproic acid (VPA, 1) is a major broad spectrum antiepileptic and central nervous system drug widely used to treat epilepsy, bipolar disorder, and migraine. VPA’s clinical use is limited by two severe and life-threatening side effects, teratogenicity and hepatotoxicity. A number of VPA analogues and their amide, N-methylamide and urea derivatives, were synthesized and evaluated in animal models of

  丙戊酸（VPA，1）是主要的广谱抗癫痫药和中枢神经系统药物，广泛用于治疗癫痫，双相情感障碍和偏头痛。VPA的临床使用受到两种严重且危及生命的副作用，致畸性和肝毒性的限制。合成了许多VPA类似物及其酰胺，N-甲基酰胺和尿素衍生物，并在神经性疼痛和癫痫的动物模型中进行了评估。其中，两种酰胺和两种尿素衍生物（1）作为抗神经痛药的效价最高，酰胺（19和20）的ED 50值分别为49和51 mg / kg，尿素衍生物的ED 50值为49和74 mg / kg。 （29和33）。19，20，和29是等效于加巴喷丁，用于治疗神经性疼痛的主要药物。这些数据表明上述新型化合物作为用于治疗神经性疼痛的未来药物开发的候选物的巨大潜力。
• BE861894
  申请人：——

  公开号：——

  公开（公告）日：——
• Syntheses and Evaluation of Anticonvulsant Profile and Teratogenicity of Novel Amide Derivatives of Branched Aliphatic Carboxylic Acids with 4-Aminobenzensulfonamide
  作者：Naama Hen、Meir Bialer、Bogdan Wlodarczyk、Richard H. Finnell、Boris Yagen

  DOI：10.1021/jm100170w

  日期：2010.5.27

  Despite the availability of 14 new antiepileptic drugs (AEDs), about 30% of epileptic patients are not seizure-free. Consequently there is substantial need to develop new effective AEDs. A novel class of aromatic amides composed of phenylacetic acid or branched aliphatic carboxylic acids, with five to nine carbons in their carboxylic moiety, and aminobenzenesulfonamide were synthesized and evaluated in the anticonvulsant rat-maximal electroshock (MES) and subcutaneous metrazol seizure (scMet) tests. Fourteen of the synthesized amides had an anticonvulsant ED(50) of <50 mg/kg in the rat-MES test. The amides 2-methyl-N-(4-sulfamoylphenyl)butyramide (10), 2-ethyl-N-(4-sulfamoylphenyl)butyramide (11), and 3,3-dimethyl-N-(4-sulfamoylphenyl)butyramide (15) were the most potent compounds possessing MES-ED(50) values of 7.6, 9.9, and 9.4 mg/kg and remarkable protective index (PI = TD(50)/ ED(50)) values of 65.7, 50.5, and 53.2, respectively. These potent sulfanylamides caused neural tube defects only at doses markedly exceeding their effective dose. The anticonvulsant properties of these compounds make them potential candidates for further development as new, potent, and safe AEDs.
• Pharmacodynamic and pharmacokinetic analysis of CNS-active constitutional isomers of valnoctamide and sec-butylpropylacetamide — Amide derivatives of valproic acid
  作者：Hafiz Mawasi、Tawfeeq Shekh-Ahmad、Richard H. Finnell、Bogdan J. Wlodarczyk、Meir Bialer

  DOI：10.1016/j.yebeh.2015.02.040

  日期：2015.5

  Valnoctamide (VCD) and sec-butylpropylacetamide (SPD) are CNS-active closely related amide derivatives of valproic acid with unique anticonvulsant activity. This study evaluated how small chemical changes affect the pharmacodynamics (PD; anticonvulsant activity and teratogenicity) and pharmacokinetics (PK) of three constitutional isomers of SPD [sec-butylisopropylacetamide (SID) and tert-butylisopropylacetamide (TID)] and of VCD [tert-butylethylacetamide (TED)]. The anticonvulsant activity of SID, TID, and TED was comparatively evaluated in several rodent anticonvulsant models. The PK-PD relationship of SID, TID, and TED was evaluated in rats, and their teratogenicity was evaluated in a mouse strain highly susceptible to teratogen-induced neural tube defects (NTDs). sec-Butylisopropylacetamide and TID have a similar PK profile to SPD which may contribute to their similar anticonvulsant activity. tert-Butylethylacetamide had a better PK profile than VCD (and SPD); however, this did not lead to a superior anticonvulsant activity. sec-Butylisopropylacetamide and TED did not cause NTDs at doses 4-7 times higher than their anticonvulsant ED50 values. In rats, SID, TID (ip), and TED exhibited a broad spectrum of anticonvulsant activity. However, combined anticonvulsant analysis in mice and rats shows SID as the most potent compound with similar activity to that of SPD, demonstrating that substitution of the isobutyl moiety in the SPD or VCD molecule by tert-butyl as well as a propyl-to-isopropyl replacement in the SPD molecule did not majorly affect the anticonvulsant activity. (C) 2015 Elsevier Inc. All rights reserved.
• Lion, Claude; Dubois, Jacques-Emile, Journal of Chemical Research, Miniprint, 1980, # 2, p. 565 - 576
  作者：Lion, Claude、Dubois, Jacques-Emile

  DOI：——

  日期：——