methyl 2-bromo-5-chloropentanoate | 138542-11-7

• 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 2-bromo-5-chloropentanoate
• 英文别名: methyl 2-bromo-5-chlorovalerate
• CAS: 138542-11-7
• 化学式: C₆H₁₀BrClO₂
• 分子量: 229.501
• InChiKey: HFRNWXMIMIPGQB-UHFFFAOYSA-N

物化性质

• 沸点：
  239.6±25.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-5-chloropentanoate 在 sodium hydride 、 二异丁基氢化铝 、 sodium iodide 作用下， 以 甲醇 、 正己烷 、 丙酮 、 甲苯 为溶剂， 反应 24.81h， 生成 tert-butyl 7-iodo-4-methoxy-2(E)-heptenoate
  参考文献：
  名称：

  Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles

  摘要：

  The stereochemistry of some lithium-iodine exchange-initiated cyclization reactions of model omega-iodo, gamma-substituted activated olefins has been studied. The stereoselectivities of these anionic cyclization reactions have been found to be a function of the olefin activator employed, reaction conditions, Michael acceptor olefin geometry, the nature of the gamma-substituent, and, in some cases, the presence of additives. Cyclization reactions of iodides possessing E olefin geometry give a moderate preference for trans cyclopentane formation while Z olefin geometry leads to extremely high (> 300:1) trans product selectivity. Cyclization reactions of E olefins under radical conditions were found to be slightly more trans-selective than those observed under anionic conditions although Z olefin geometry again promotes very high trans product selectivity. The presence of the allylic methoxyl group in (E)-7d leads to cis selectivity under both anionic and radical conditions. Intramolecular complexation involving the reactive carbon center and the methoxyl group is suggested in both modes as a possible explanation for this cis product selectivity.

  DOI：

  10.1021/jo00031a031
• 作为产物：
  描述：

  甲醇 、 5-氯戊酸 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 氢溴酸 作用下， 生成 methyl 2-bromo-5-chloropentanoate
  参考文献：
  名称：

  Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles

  摘要：

  The stereochemistry of some lithium-iodine exchange-initiated cyclization reactions of model omega-iodo, gamma-substituted activated olefins has been studied. The stereoselectivities of these anionic cyclization reactions have been found to be a function of the olefin activator employed, reaction conditions, Michael acceptor olefin geometry, the nature of the gamma-substituent, and, in some cases, the presence of additives. Cyclization reactions of iodides possessing E olefin geometry give a moderate preference for trans cyclopentane formation while Z olefin geometry leads to extremely high (> 300:1) trans product selectivity. Cyclization reactions of E olefins under radical conditions were found to be slightly more trans-selective than those observed under anionic conditions although Z olefin geometry again promotes very high trans product selectivity. The presence of the allylic methoxyl group in (E)-7d leads to cis selectivity under both anionic and radical conditions. Intramolecular complexation involving the reactive carbon center and the methoxyl group is suggested in both modes as a possible explanation for this cis product selectivity.

  DOI：

  10.1021/jo00031a031

文献信息

• Acetylenic &agr;-amino acid-based sulfonamide hydroxamic acid tace inhibitors
  申请人：American Cyanamid Company

  公开号：US06225311B1

  公开（公告）日：2001-05-01

  Compounds of the formula: are useful in treating disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  该式化合物在治疗由TNF-α介导的疾病条件中很有用，如类风湿性关节炎、骨关节炎、败血症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和软骨退行性损失。
• Substituted tricyclics
  申请人：Eli Lilly and Company

  公开号：US06177440B1

  公开（公告）日：2001-01-23

  A class of novel tricyclics is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of conditions such as septic shock.

  一类新型三环化合物被披露，以及利用这类化合物抑制sPLA2介导的脂肪酸释放，用于治疗诸如感染性休克等疾病。
• [EN] IMPROVED PROCESS FOR THE MANUFACTURE OF 1,2-DISUBSTITUTED HEXAHYDROPYRIDAZINE-3-CARBOXYLIC ACIDS AND ESTERS THEREOF<br/>[FR] PROCEDE AMELIORE DE FABRICATION D'ACIDES HEXAHYDROPYRIDAZINE-3-CARBOXYLIQUES 1,2-DISUBSTITUES ET LEURS ESTERS
  申请人：HONEYWELL SPECIALTY CHEMICALS

  公开号：WO2005028449A1

  公开（公告）日：2005-03-31

  The invention relates to an improved process for the manufacture of 1,2-disubstituted hexahydro-pyridazine-3-carboxylic acids and esters thereof by reacting N,N’-disubstituted hydrazine with 2,5-dihalogenated valeric acids and thereof by means of phase transfer catalysis. Said pyridazine carboxylic acids and esters thereof can be used as intermediates for the production of pharmaceutical products

  该发明涉及一种改进的工艺，通过相转移催化作用，将N,N'-二取代肼与2,5-二卤代戊二酸反应，制备1,2-二取代六氢吡啶并-3-羧酸及其酯。所述吡啶羧酸及其酯可用作制药产品的中间体。
• Polymethylene Derivatives of Nucleic Bases Bearing ω-Functional Groups: Х. A Novel Approach to the Synthesis of α-Amino-ω-Nucleo Carboxylic Acids
  作者：V. V. Komissarov、A. M. Kritsyn

  DOI：10.1134/s1068162018050060

  日期：2018.11

  A novel approach to the synthesis of α-amino-ω-nucleo carboxylic acids, analogs of willardiin, an activator of the receptor of α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid, which is responsible for the transfer of a fast stimulating signal in the synapses of the nervous system of vertebrates, is proposed. Based on substantial differences in the reactivity of halogen atoms in α,ω-dihalogen

  一种合成 α-氨基-ω-核羧酸的新方法，willardiin 的类似物，α-氨基-3-羟基-5-甲基-4-异恶唑丙酸受体的活化剂，它负责提议在脊椎动物神经系统的突触中传递快速刺激信号。基于 α,ω-二卤代羧酸中卤原子反应性的显着差异，合成了 α-邻苯二甲酰亚氨基-ω-氯羧酸的酯。尿嘧啶、胸腺嘧啶和腺嘌呤与这些酯的烷基化得到了关键化合物，即 α-邻苯二甲酰亚氨基-ω-核羧酸的酯。邻苯二甲酰基保护基团的连续去除和酸水解导致新的核酸碱基多亚甲基衍生物，即α-氨基-ω-核羧酸。
• Polymethylene derivatives of nucleic bases bearing ω-functional groups: IX—An unusual reaction of methyl 2-thiocyano-5-chloropentanoate with uracyl and thymine
  作者：V. V. Komissarov、A. M. Kritzyn

  DOI：10.1134/s1068162017060061

  日期：2017.11

  decades, potential inhibitors of the enzymes bearing thiocyano groups have been little studied. In this work, we tried to synthesize polymethylene derivatives of nucleic bases bearing thiocyano groups at the ω-position of the polymethylene chain. The reaction of new alkylating reagents, methyl α-thiocyano-ω-chloroalkanoates, with nucleic bases led to a complicated and barely separated product mixture.

  尽管在过去的几十年中寻找 HIV 复制关键酶的抑制剂仍然是一个热门话题，并进行了深入研究，但对带有硫氰基的酶的潜在抑制剂的研究却很少。在这项工作中，我们试图合成在聚亚甲基链的 ω 位带有硫氰基的核酸碱基的聚亚甲基衍生物。新的烷基化试剂 α-硫氰基-ω-氯代链烷酸甲酯与核酸碱基的反应导致了复杂且几乎不分离的产物混合物。唯一的例外是尿嘧啶或胸腺嘧啶与 2-硫氰基-2-氯戊酸甲酯的反应，其中 2-（N1-尿嘧啶基或 -胸腺嘧啶基）四氢噻吩-2-羧酸盐的分离产率为 45-50%。讨论了该反应的潜在机制。