ethyl 5-bromohexanoate | 90202-08-7

• 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: ethyl 5-bromohexanoate
• 英文别名: 5-bromo-hexanoic acid ethyl ester；5-Brom-hexansaeure-aethylester；5-Brom-capronsaeure-aethylester
• CAS: 90202-08-7
• 化学式: C₈H₁₅BrO₂
• 分子量: 223.11
• InChiKey: BUEKMBOIHDZAPT-UHFFFAOYSA-N

物化性质

• 沸点：
  211.35°C (rough estimate)
• 密度：
  1.3542 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  ethyl 5-bromohexanoate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 2-(dibutylphosphanyl)-1-phenylpyrrole 、 氢气 、 magnesium 、 lithium chloride 、 zinc(II) chloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 6-(2-Aminophenyl)hexanoic acid
  参考文献：
  名称：

  区域收敛交叉偶联对烷基链的末端选择性官能化

  摘要：

  碳氢化合物仍然是功能化有机分子的最重要前体，在新型CH键功能化方法的发现中引起了人们的兴趣。我们在这里描述了一种新的步骤经济的方法，该方法使C-C键能够在直链烷烃的末端位置进行构建。首先，我们表明仲烷基溴化物可以原位转化为烷基溴化锌和与会聚芳基或烯基三氟甲磺酸酯的区域收敛的Negishi。使用合适的膦配体促进Pd迁移，可以选择性形成线性交叉偶联产物。随后，通过标准溴化反应，由直链烷烃制备仲烷基溴化物的混合物，然后通过区域会聚交叉偶联，仅需两个步骤即可获得相应的线性芳基化产物。

  DOI：

  10.1002/anie.201608535
• 作为产物：
  描述：

  5-羟基己酸乙酯 在 三甲基溴硅烷 作用下， 以 氯仿 为溶剂， 反应 27.0h， 生成 ethyl 5-bromohexanoate
  参考文献：
  名称：

  Aliphatic propargylamines: potent, selective, irreversible monoamine oxidase B inhibitors

  摘要：

  A series of aliphatic propargylamine derivatives has been synthesized. Some of them possess highly potent, irreversible, selective, inhibitory activity toward monoamine oxidase B (MAO-B). The potency of the inhibitors is related to chain length and substitution of a hydrogen on the terminal carbon of the aliphatic chain. MAO inhibitory activity as assessed in vitro increased as the aliphatic carbon chain length increased. Substitution of a hydrogen by hydroxyl, carboxyl, or carbethoxyl groups at the aliphatic chain terminal or replacement of the methyl group on the nitrogen atom by an ethyl group considerably reduced the inhibitory activity. Stereospecific effects were observed with the R-(-)-enantiomer being 20-fold more active than the S-(+)-enantiomer. Inhibitors with relatively short carbon chain lengths (i.e. four to six carbons) were found to be more potent than those with longer chains in inhibiting brain MAO-B activity in vivo especially after oral administration. Chronic administration of low doses of the aliphatic propargylamines caused a slight cumulative inhibition of MAO-A activity in the mouse brain. These MAO-B inhibitors appear to be nontoxic, and they do not possess an amphetamine-like moiety in their structure as is the case for deprenyl. We expect that these aliphatic propargylamines may be useful in the treatment in certain neuropsychiatric disorders.

  DOI：

  10.1021/jm00098a017

文献信息

• [EN] 2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS<br/>[FR] DERIVES DE L'ACIDE 2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIQUE EN TANT QU'ANTAGONISTES DE CRTH2
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2006021418A1

  公开（公告）日：2006-03-02

  The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent 'chemoattractant receptor-homologous molecule expressed on Th2 cells' antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

  这项发明涉及2-硫代基苯并咪唑-1-基乙酸衍生物及其在治疗前列腺素介导的疾病中作为强效“趋化受体同源分子在Th2细胞上表达”的拮抗剂的用途，涉及含有这些衍生物的药物组合物以及其制备方法。
• Process and method for the preparation of asymmetric monfunctionalised indocyanine labelling reagents and obtained compounds
  申请人：——

  公开号：US20020065421A1

  公开（公告）日：2002-05-30

  A process for preparing an asymmetrical indocyanine dye comprising the steps of: a) reacting a first quaternised indolenine or substituted indolenine with a compound of the formula (II) 1 or hydrochloride thereof, wherein n is 0 or 1 Ph is phenyl or substituted phenyl X is hydrogen, halogen or alkyl, preferably chlorine, in a solvent selected from the group consisting of acetic acid, acetic anhydride and mixtures thereof in the presence of acetyl chloride, to obtain an intermediate hemicyanine, and b) further reacting said intermediate hemicyanine with a second quaternised indolenine or substituted indolenine different from said first indolenine.

  制备不对称吲哚靛染料的过程包括以下步骤：a）将第一季铵化吲哚啉或取代吲哚啉与式（II）1的化合物或其盐酸盐反应，其中n为0或1，Ph为苯基或取代苯基，X为氢、卤素或烷基，优选为氯，在乙酸、乙酸酐及其混合物中，在乙酰氯的存在下，获得中间体半青霉素，b）进一步将所述中间体半青霉素与第二季铵化吲哚啉或不同于所述第一吲哚啉的取代吲哚啉反应。
• The first palladium-catalyzed Sonogashira coupling of unactivated secondary alkyl bromides
  作者：Gereon Altenhoff、Sebastian Würtz、Frank Glorius

  DOI：10.1016/j.tetlet.2006.02.111

  日期：2006.4

  A palladium-carbene catalyzed Sonogashira coupling of unactivated alkyl bromides with alkyl substituted alkynes is reported. For the first time, unactivated secondary alkyl halides were successfully employed in Sonogashira reactions.

  报道了未活化的烷基溴与烷基取代的炔烃的钯-卡宾催化的Sonogashira偶联。首次将未活化的仲烷基卤化物成功用于Sonogashira反应。
• Compounds and Methods of Use Thereof
  申请人：Dyakonov Tatyana

  公开号：US20080269204A1

  公开（公告）日：2008-10-30

  Benzolactam boronic acid compounds and pharmaceutical formulations are described along with methods of use thereof for inhibiting inflammatory cytokines such as tumor necrosis factor alpha (TNF-α) in a subject in need thereof.

  本发明涉及苯内酰胺硼酸化合物和药物制剂，以及使用它们的方法，用于抑制需要抑制炎症细胞因子如肿瘤坏死因子α（TNF-α）的患者中的细胞因子。
• Process and method for the preparation of asymetric monfunctionalised indocyanine labelling reagents and obtained compounds
  申请人：Caputo Giuseppe

  公开号：US20050245734A1

  公开（公告）日：2005-11-03

  A process for preparing an asymmetrical indocyanine dye comprising the steps of: a) reacting a first quaternised indolenine or substituted indolenine with a compound of the formula (II) or hydrochloride thereof, wherein n is 0 or 1 Ph is phenyl or substituted phenyl X is hydrogen, halogen or alkyl, preferably chlorine, in a solvent selected from the group consisting of acetic acid, acetic anhydride and mixtures thereof in the presence of acetyl chloride, to obtain an intermediate hemicyanine, and b) further reacting said intermediate hemicyanine with a second quaternised indolenine or substituted indolenine different from said first indolenine.

  制备一种不对称吲哚氰染料的过程，包括以下步骤：a）将第一季铵化吲哚啉或取代吲哚啉与式（II）化合物或其盐酸盐反应，其中n为0或1，Ph为苯基或取代苯基，X为氢、卤素或烷基，优选氯，在乙酸、乙酸酐及其混合物中，在乙酰氯存在下，得到中间体半环氰染料；b）进一步将所述中间体半环氰染料与第二个不同于所述第一吲哚啉的季铵化吲哚啉或取代吲哚啉反应。