1-bromo-4-methylheptane | 88467-55-4

• 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: 1-bromo-4-methylheptane
• CAS: 88467-55-4
• 化学式: C₈H₁₇Br
• 分子量: 193.127
• InChiKey: MRLAKDCGXYAZCI-UHFFFAOYSA-N

物化性质

• 沸点：
  191.87°C (estimate)
• 密度：
  1.1024 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  9
• 可旋转键数：
  5
• 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：

  1-bromo-4-methylheptane 在 immobilised Candida rugosa Lipase 氢氧化钾 、 1-十六烷醇 、 lithium 、 sodium sulfate 作用下， 以 乙醇 、 正己烷 、 环己烷 为溶剂， 反应 3.0h， 生成 (R)-7-Methyl-decanoic acid
  参考文献：
  名称：

  Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids

  摘要：

  Several racemic methyl decanoic acids have been synthesised and Successfully resolved in esterification with 1-hexadecanol at a(w)=0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E=2.8-68) obtained were surprisingly high even when the methyl group was as remotely located as in 8-methyldecanoic acid (E=25). Interestingly, the lipase shows enantiopreference for the S-enantiomer when the methyl group is located on even numbered carbons i.e. for the 2-,4-,6- and 8-methyldecanoic acids and to the R-enantiomer when the methyl group is located on uneven numbered carbons i.e. for the 3-,5- and 7-methyldecanoic acids. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00172-6
• 作为产物：
  描述：

  2-甲基-1-戊醇 在 磷化氢 、 氢氧化钾 、 lithium aluminium tetrahydride 、 溴 、 sodium ethanolate 、 三苯基膦 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 8.12h， 生成 1-bromo-4-methylheptane
  参考文献：
  名称：

  Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids

  摘要：

  Several racemic methyl decanoic acids have been synthesised and Successfully resolved in esterification with 1-hexadecanol at a(w)=0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E=2.8-68) obtained were surprisingly high even when the methyl group was as remotely located as in 8-methyldecanoic acid (E=25). Interestingly, the lipase shows enantiopreference for the S-enantiomer when the methyl group is located on even numbered carbons i.e. for the 2-,4-,6- and 8-methyldecanoic acids and to the R-enantiomer when the methyl group is located on uneven numbered carbons i.e. for the 3-,5- and 7-methyldecanoic acids. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00172-6

文献信息

• Pheromone, XXV. Alkylverzweigte Analoge von Lepidopterenpheromonen
  作者：Hans Jürgen Bestmann、Peter Rösel、Otto Vostrowsky

  DOI：10.1002/jlac.197919790813

  日期：1979.8.29

  Alkyl(triphenyl)phosphoniumsalze mit verzweigter Alkylkette lassen sich nach verschiedenen Methoden aufbauen und durch Z-stereoselektive Wittig-Reaktion mit geeigneten Aldehyden in Analoge von Schmetterlings-Pheromonen (Lepidoptera) überführen. - Die Ergebnisse der elektro-physiologischen Messungen (Elektroantennogramm, EAG) mit den solcherart synthetisierten Verbindungen führten zu einem Modell dynamischer

  具有支链烷基链的烷基（三苯基）phospho盐可以通过各种方法合成，并通过Z-立体选择性Wittig反应与合适的醛转化为蝴蝶信息素（鳞翅目）的类似物。-用这种方法合成的化合物进行的电生理测量结果（电生理曲线图，EAG）导致了信息素与受体区域之间动态相互作用的模型。
• Seizure Control by Derivatives of Medium Chain Fatty Acids Associated with the Ketogenic Diet Show Novel Branching-Point Structure for Enhanced Potency
  作者：Pishan Chang、Alexandra M. E. Zuckermann、Sophie Williams、Adam J. Close、Marife Cano-Jaimez、James P. McEvoy、John Spencer、Matthew C. Walker、Robin S. B. Williams

  DOI：10.1124/jpet.114.218768

  日期：2015.1

  The medium chain triglyceride (MCT) ketogenic diet is a major treatment of drug-resistant epilepsy but is problematic, particularly in adults, because of poor tolerability. Branched derivatives of octanoic acid (OA), a medium chain fat provided in the diet have been suggested as potential new treatments for drug-resistant epilepsy, but the structural basis of this functionality has not been determined. Here we investigate structural variants of branched medium chain fatty acids as new seizure-control treatments. We initially employ a series of methyl-branched OA derivatives, and using the GABAA receptor antagonist pentylenetetrazol to induce seizure-like activity in rat hippocampal slices, we show a strong, branch-point–specific activity that improves upon the related epilepsy treatment valproic acid. Using low magnesium conditions to induce glutamate excitotoxicity in rat primary hippocampal neuronal cultures for the assessment of neuroprotection, we also show a structural dependence identical to that for seizure control, suggesting a related mechanism of action for these compounds in both seizure control and neuroprotection. In contrast, the effect of these compounds on histone deacetylase (HDAC) inhibition, associated with teratogenicity, shows no correlation with therapeutic efficacy. Furthermore, small structural modifications of the starting compounds provide active compounds without HDAC inhibitory effects. Finally, using multiple in vivo seizure models, we identify potent lead candidates for the treatment of epilepsy. This study therefore identifies a novel family of fatty acids, related to the MCT ketogenic diet, that show promise as new treatments for epilepsy control and possibly other MCT ketogenic diet-responding conditions, such as Alzheimer disease.

  中链甘油三酯（MCT）生酮饮食是耐药性癫痫的主要治疗方法，但由于耐受性差，存在问题，特别是在成人中。辛酸（OA）的支链衍生物是饮食中提供的一种中链脂肪，已被建议作为耐药性癫痫的潜在新疗法，但这种功能的结构基础尚未确定。在这里，我们研究支链中链脂肪酸的结构变体作为新的癫痫控制治疗方法。我们首先使用一系列甲基支化的 OA 衍生物，并使用 GABAA 受体拮抗剂戊四唑在大鼠海马切片中诱导癫痫样活性，我们显示出强烈的分支点特异性活性，该活性优于相关癫痫治疗丙戊酸。使用低镁条件在大鼠原代海马神经元培养物中诱导谷氨酸兴奋毒性以评估神经保护作用，我们还表现出与癫痫控制相同的结构依赖性，表明这些化合物在癫痫控制和神经保护方面的相关作用机制。相反，这些化合物对与致畸性相关的组蛋白脱乙酰酶（HDAC）抑制的作用与治疗效果没有相关性。此外，起始化合物的小结构修饰提供了没有HDAC抑制作用的活性化合物。最后，使用多个体内癫痫模型，我们确定了治疗癫痫的有效先导候选药物。因此，这项研究确定了一个与 MCT 生酮饮食相关的新型脂肪酸家族，该家族有望成为控制癫痫和其他可能对 MCT 生酮饮食有反应的疾病（例如阿尔茨海默病）的新疗法。
• 6,12-dimethylpentadecan-2-one and its use in monitoring and controlling
  申请人：The United States of America as represented by the Secretary of

  公开号：US04871537A1

  公开（公告）日：1989-10-03

  A pheromonal compound produced by the banded cucumber beetle has been identified as 6,12-dimethylpentadecan-2-one. Both the synthetically prepared racemic compound and the purified natural pheromone elicited responses by banded cucumber males in field tests. By attracting adult beetles to field traps, this compound is a useful tool for the monitoring and controlling of this major agricultural pest.

  一种由花斑黄瓜甲虫产生的信息素化合物已被鉴定为6,12-二甲基十五烷酮。在野外测试中，合成的外消旋化合物和纯化的天然信息素均能引起花斑黄瓜甲虫雄虫的反应。通过将成虫诱引至田间陷阱，该化合物是监测和控制这一重要农业害虫的有用工具。
• Cason et al., Journal of the American Chemical Society, 1944, vol. 66, p. 1766
  作者：Cason et al.

  DOI：——

  日期：——
• Shonle et al., Journal of the American Chemical Society, 1936, vol. 58, p. 586
  作者：Shonle et al.

  DOI：——

  日期：——