(R)-1-bromo-2-methylpentane | 149065-61-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (R)-1-bromo-2-methylpentane
• 英文别名: (2R)-1-bromo-2-methylpentane
• CAS: 149065-61-2
• 化学式: C₆H₁₃Br
• 分子量: 165.073
• InChiKey: GSYMWZIKZUHBKV-ZCFIWIBFSA-N

物化性质

• 沸点：
  144.0±8.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (R)-1-bromo-2-methylpentane 在 Amano lipase PS-SD 、 potassium tert-butylate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成 methyl (3S,5R)-3-cyano-5-methyloctanoate
  参考文献：
  名称：

  Chemical Development of an α2δ Ligand, (3S,5R)-3-(Aminomethyl)-5-methyloctanoic Acid

  摘要：

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.

  DOI：

  10.1021/op2001832
• 作为产物：
  描述：

  2-甲基-1-戊醇 在 Amano lipase PS-C₁ 、 四丁基溴化铵 、 三乙胺 、 sodium bromide 作用下， 以 二氯甲烷 、 甲基叔丁基醚 、 水 为溶剂， 反应 19.0h， 生成 (R)-1-bromo-2-methylpentane
  参考文献：
  名称：

  Chemical Development of an α2δ Ligand, (3S,5R)-3-(Aminomethyl)-5-methyloctanoic Acid

  摘要：

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.

  DOI：

  10.1021/op2001832

文献信息

• Regio- and Stereochemical Study of Sex Pheromone of Pine Sawfly;<i>Diprion</i><i>nipponica</i>
  作者：Akira Tai、Emi Syouno、Kazuki Tanaka、Morifumi Fujita、Takashi Sugimura、Yasutomo Higashiura、Masashi Kakizaki、Hideho Hara、Tikahiko Naito

  DOI：10.1246/bcsj.75.111

  日期：2002.1

  Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5–9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females

  1,2,ω-丙酸三甲基癸酯 (ω = 5–9) 的区域异构体和立体异构体是从立体化学纯手性构件中制备的，作为松叶蜂的性信息素候选物；Diprion nipponica。在合成的候选物中，根据其 GC-MS 数据与雌性提取物的 GC-MS 数据的兼容性，发现 (1S,2R,8S)-1,2,8-trimethyldecyl propionate 是 D. nipponica 的性信息素，及其在野外生物测定中显着的高信息素活性。合成化合物的现场生物测定还表明，(1S,2R,8R)-1,2,8-丙酸三甲基癸酯、(1S,2R,7S)-1,2,7-丙酸三甲酯和 (1S,2R, 6S)-1,2,6-trimethyldecyl propionate 可以作为信息素模拟物在一定程度上吸引雄性锯蝇。
• [EN] TREATMENT OF INTERSTITIAL CYSTITIS<br/>[FR] TRAITEMENT DE LA CYSTITE INTERSTITIELLE
  申请人：PFIZER

  公开号：WO2009136375A1

  公开（公告）日：2009-11-12

  The present invention relates to the use of (3S,5R)-3-aminomethyl-5-methyloctanoic acid, or a pharmaceutically acceptable salt or solvate thereof, for the treatment of a pain and/or a lower urinary tract symptom(s) (LUTS) associated with interstitial cystitis and/or painful bladder syndrome and/or bladder pain syndrome.
• Chemical Development of an α2δ Ligand, (3<i>S</i>,5<i>R</i>)-3-(Aminomethyl)-5-methyloctanoic Acid
  作者：Lorraine Murtagh、Catherine Dunne、Gino Gabellone、Niamh J. Panesar、Stuart Field、Lisa M. Reeder、James Saenz、George P. Smith、Kyle Kissick、Carlos, Martinez、John G. Van Alsten、Margaret C. Evans、Lloyd C. Franklin、Thomas Nanninga、John Wong

  DOI：10.1021/op2001832

  日期：2011.11.18

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.