methyl 6-(methoxycarbonyl)-2,2-dimethylhexanoate | 142423-11-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-(methoxycarbonyl)-2,2-dimethylhexanoate
• 英文别名: Dimethyl 2,2-dimethylheptanedioate
• CAS: 142423-11-8
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: GKMBDCMTHBRTCU-UHFFFAOYSA-N

物化性质

• 沸点：
  233.2±8.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-(methoxycarbonyl)-2,2-dimethylhexanoate 在 氢氧化钾 、 氯化亚砜 、 四氯化锡 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 53.0h， 生成 2,2-dimethyl-7-<5-methyl-3-(3-phenylpropyl)-2-thienyl>heptanoic acid
  参考文献：
  名称：

  .omega.-[(.omega.-Arylalkyl)thienyl]alkanoic acids: from specific LTA4 hydrolase inhibitors to LTB4 receptor antagonists

  摘要：

  A series of omega-[(omega-arylalkyl)thienyl]alkanoic acid isomers was prepared and a structure-activity relationship was investigated. These compounds have displayed either LTA, hydrolase inhibition activities or LTB4 receptor binding activities, or both, depending on the relative orientation of the two side chains on the thiophene ring. Whereas the 2,5-isomers specifically exhibited LTA4 hydrolase inhibition, 3,5-isomers displayed both activities. On the other hand, the ''ortho-isomers'' specifically inhibited the binding of the LTB4 to its receptor. The side-chain lengths were also important for an optimal inhibition or binding activity. Substitutions on the terminal aromatic ring or on the thiophene nucleus led to small changes in both activities. The most dramatic effect was obtained by substituting the carboxylic acid side chain in the alpha-position with one or two methyl groups, which substantially enhanced the LTB4 receptor binding activity. In the most favorable case, the alpha,alpha-dimethyl derivative RP66153 was found 20-fold more potent than its linear counterpart.

  DOI：

  10.1021/jm00095a011
• 作为产物：
  描述：

  2,2-二甲基环己酮 在 sodium hydride 作用下， 生成 methyl 6-(methoxycarbonyl)-2,2-dimethylhexanoate
  参考文献：
  名称：

  直接催化不对称烯醛缩醛化。

  摘要：

  DOI：

  10.1002/anie.200351266

文献信息

• A new method of one-pot synthesis of dicarboxylic acid derivatives and diketones containing quaternary carbon atom and remote functional groups from linear acyl halides
  作者：Irena S. Akhrem、Dzhul'etta V. Avetisyan、Lyudmila V. Afanas'eva、Oleg I. Artyushin、Nikolai D. Kagramanov、Andrey L. Sigan

  DOI：10.1016/j.tetlet.2017.09.019

  日期：2017.10

  The one-pot, regioselective synthesis of branched diacid derivatives – diesters, dithioesters, diamides [YC(O)O(CH2)mC(Me)2OC(O)Y] and diketones of aromatic and heteroaromatic series, [ArCO(CH2)mC(Me)2C(O)Ar,) from available linear acyl halides, CnH2 n+1COCl (n = 7–9), CO (1 at) and various nucleophiles (YH = EtOH, CF3CH2OH, H(CF2)2CH2OH, thiophene, anisole, Et2NH, aniline, and morpholine) in the presence

  一锅的区域选择性合成支链二酸衍生物–二酯，二硫酯，二酰胺[YC（O）O（CH 2）m C（Me）2 OC（O）Y]以及芳族和杂芳族系列的二酮[ArCO（ CH 2）m C（Me）2 C（O）Ar，）来自可用的线性酰基卤，C n H 2  n + 1 COCl（n = 7–9），CO（1 at）和各种亲核试剂（YH = EtOH ，CF 3 CH 2 OH，H（CF 2）2 CH 2 OH，噻吩，苯甲醚，Et 2 NH，苯胺和吗啉）在超亲电子配合物CBr 4的存在下·2AlBr 3首次进行。该方法提供了获得新的和有希望的二元羧酸衍生物和含有季碳原子和远端官能团的二酮基的途径。
• Direct Catalytic Asymmetric Enolexo Aldolizations
  作者：Chandrakala Pidathala、Linh Hoang、Nicola Vignola、Benjamin List

  DOI：10.1002/anie.200351266

  日期：2003.6.23
• .omega.-[(.omega.-Arylalkyl)thienyl]alkanoic acids: from specific LTA4 hydrolase inhibitors to LTB4 receptor antagonists
  作者：Richard Labaudiniere、Gerd Hilboll、Alicia Leon-Lomeli、Bernard Terlain、Francoise Cavy、Michael Parnham、Peter Kuhl、Norbert Dereu

  DOI：10.1021/jm00095a011

  日期：1992.8

  A series of omega-[(omega-arylalkyl)thienyl]alkanoic acid isomers was prepared and a structure-activity relationship was investigated. These compounds have displayed either LTA, hydrolase inhibition activities or LTB4 receptor binding activities, or both, depending on the relative orientation of the two side chains on the thiophene ring. Whereas the 2,5-isomers specifically exhibited LTA4 hydrolase inhibition, 3,5-isomers displayed both activities. On the other hand, the ''ortho-isomers'' specifically inhibited the binding of the LTB4 to its receptor. The side-chain lengths were also important for an optimal inhibition or binding activity. Substitutions on the terminal aromatic ring or on the thiophene nucleus led to small changes in both activities. The most dramatic effect was obtained by substituting the carboxylic acid side chain in the alpha-position with one or two methyl groups, which substantially enhanced the LTB4 receptor binding activity. In the most favorable case, the alpha,alpha-dimethyl derivative RP66153 was found 20-fold more potent than its linear counterpart.