1,5-二甲基己基甲苯磺酸酯 | 102736-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,5-二甲基己基甲苯磺酸酯
• 英文名称: 1,5-dimethylhexyl tosylate
• 英文别名: 6-Methylheptan-2-yl 4-methylbenzenesulfonate
• CAS: 102736-18-5
• 化学式: C₁₅H₂₄O₃S
• 分子量: 284.42
• InChiKey: QYLHEARTGIQUIS-UHFFFAOYSA-N

物化性质

• 沸点：
  382.2±11.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5-二甲基己基甲苯磺酸酯 在 乙醇 、 硫酸 、 sodium hydroxide 作用下， 反应 27.5h， 生成 1,5-二甲基己烷-1-羧酸
  参考文献：
  名称：

  Synthesis and characterization of cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA

  摘要：

  The measurement of acyl-CoA dehydrogenase activities is an essential part of the investigation of patients with suspected defects in fatty acid oxidation. Multiple methods are available for the synthesis of the substrates used for measuring acyl-CoA dehydrogenase activities: however, the yields are low and the products are used without purification. In addition, the reported characterization of acyl-CoAs focuses on the CoA moiety, not on the acyl group. Here we describe the synthesis of three medium-chain acyl-CoAs from mixed anhydrides of the fatty acids using an aqueous-organic solvent mixture optimized to obtain the highest yield. First, cis-4-decenoic acid and 2,6-dimethylheptanoic acid were prepared (3-phenylpropionic acid is commercially available). These were characterized by gas chromatography/mass spectrometry (GC/MS), H-1 nuclear magnetic resonance (NMR), and C-13 NMR. Then cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA were synthesized. These were then purified by ion exchange solid-phase extraction using 2-(2-pyridyl)ethyl-functionalized silica gel, followed by reversed-phase semipreparative high-performance liquid chromatography with ultraviolet detection (HPLC-UV). The purified acyl-CoAs were characterized by analytical HPLC-UV followed by data-dependent tandem mass spectrometry (MS/MS) analysis on the largest responding MS mass (HPLC-UV-MS-MS/MS) and 13C NMR. The yields of the purified acyl-CoAs were between 75% and 78% based on coenzyme A trilithium salt (CoASH). Acyl-CoA dehydrogenase activities were measured in rat skeletal muscle mitochondria using, as substrates, the synthesized cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA. These results were compared with the results using our standard substrates butyryl-CoA, octanoyl-CoA, and palmitoyl-CoA. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2010.02.026
• 作为产物：
  描述：

  6-甲基-2-庚醇 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 18.0h， 生成 1,5-二甲基己基甲苯磺酸酯
  参考文献：
  名称：

  Synthesis and characterization of cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA

  摘要：

  The measurement of acyl-CoA dehydrogenase activities is an essential part of the investigation of patients with suspected defects in fatty acid oxidation. Multiple methods are available for the synthesis of the substrates used for measuring acyl-CoA dehydrogenase activities: however, the yields are low and the products are used without purification. In addition, the reported characterization of acyl-CoAs focuses on the CoA moiety, not on the acyl group. Here we describe the synthesis of three medium-chain acyl-CoAs from mixed anhydrides of the fatty acids using an aqueous-organic solvent mixture optimized to obtain the highest yield. First, cis-4-decenoic acid and 2,6-dimethylheptanoic acid were prepared (3-phenylpropionic acid is commercially available). These were characterized by gas chromatography/mass spectrometry (GC/MS), H-1 nuclear magnetic resonance (NMR), and C-13 NMR. Then cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA were synthesized. These were then purified by ion exchange solid-phase extraction using 2-(2-pyridyl)ethyl-functionalized silica gel, followed by reversed-phase semipreparative high-performance liquid chromatography with ultraviolet detection (HPLC-UV). The purified acyl-CoAs were characterized by analytical HPLC-UV followed by data-dependent tandem mass spectrometry (MS/MS) analysis on the largest responding MS mass (HPLC-UV-MS-MS/MS) and 13C NMR. The yields of the purified acyl-CoAs were between 75% and 78% based on coenzyme A trilithium salt (CoASH). Acyl-CoA dehydrogenase activities were measured in rat skeletal muscle mitochondria using, as substrates, the synthesized cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA. These results were compared with the results using our standard substrates butyryl-CoA, octanoyl-CoA, and palmitoyl-CoA. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2010.02.026

文献信息

• Rates and alkyl group size in solvolysis of alkyl derivatives
  作者：Mirko Orlovic、Olga Kronja、Kresimir Humski、Stanko Borcic、Eugenio Polla

  DOI：10.1021/jo00367a001

  日期：1986.8
• Indole and benzimidazole derivatives as steroid 5α-reductase inhibitors in the rat prostate
  作者：Hitoshi Takami、Nobuyuki Kishibayashi、Akio Ishii、Toshiaki Kumazawa

  DOI：10.1016/s0968-0896(98)80018-7

  日期：1998.12

  A novel series of indole and benzimidazole derivatives were synthesized and evaluated for their inhibitory activity of rat prostatic 5 alpha-reductase. Among these compounds, 4-2-[1-(4,4'-dipropylbenzhydryl)indole-5-carboxamido]phenoxy)butyric acid (15) and its benzimidazole analogue 25 showed potent inhibitory activities for rat prostatic 5 alpha-reductase (IC50 values of 9.6+/-1.0 and 13+/-1.5 nM, respectively), with the potency very close to that of finasteride. Compound 30, in which the moiety between the benzene ring and amide bond was replaced by quinolin-4-one ring, showed almost equipotent activity (IC50=19+/-6.2 nM) with the correspondent amide derivative 13. This result was consistent with the previous observation that the coplanarity of this moiety might contribute to the potent inhibitory activity. (C) 1998 Elsevier Science Ltd. All rights reserved.