3-carboisopropoxypropionyl chloride | 36335-31-6

• 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: 3-carboisopropoxypropionyl chloride
• 英文别名: isopropyl β-(chlorocarbonyl)propionate；isopropyl 4-chloro-4-oxobutanoate；Propan-2-yl 4-chloro-4-oxobutanoate
• CAS: 36335-31-6
• 化学式: C₇H₁₁ClO₃
• 分子量: 178.616
• InChiKey: HDCOUCOKHNGTPH-UHFFFAOYSA-N

物化性质

• 沸点：
  220.3±23.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-carboisopropoxypropionyl chloride 在 三乙胺 作用下， 以 氯苯 为溶剂， 反应 13.0h， 生成 isopropyl β-(methoxycarbonylamino)propionate
  参考文献：
  名称：

  Synthesis, Characterization and Chemistry of the Fluoronitramide Anion

  摘要：

  我们合成了氟硝酰胺阴离子及其钾盐、四异丙基对苯基二胍盐和四苯基鏻盐。对后一种盐进行了详细表征，因为它是迄今为止最稳定的一种盐。游离酸 HN(F)(NO2)不稳定，氟硝胺的铵盐也是如此。事实证明，氟原子能够被亲核物置换。二硝酰胺在室温下对水碱没有反应，而氟硝酰胺却能立即与氢氧化物水溶液发生反应。单晶 X 射线衍射数据显示，在所研究的所有盐类中，氟原子的位置都具有不同寻常的不确定性。

  DOI：

  10.1055/s-2007-966004
• 作为产物：
  描述：

  4-异丙氧基-4-氧代丁酸 在 氯化亚砜 作用下， 反应 3.0h， 以78%的产率得到3-carboisopropoxypropionyl chloride
  参考文献：
  名称：

  Synthesis of Novel g-Ketoesters from Succinic Anhydride

  摘要：

  四种烷基g-酮己酸酯（3a-3d）是通过三步反应策略从琥珀酸酐制备而成。在第一步中，使用对甲苯磺酸作为催化剂，分别用异丙醇、异丁醇、异戊醇和苄醇打开琥珀酸酐的环，形成烷基氢琥珀酸酯（1a-1d）。在第二步中，这些烷基氢琥珀酸酯与SOCl2处理，生成4-烷氧基-4-酮丁酰氯（2a-2d）。所获得的酸卤化物与二乙基镉反应，得到所需的g-酮酯。所有合成的化合物通过记录和分析1H和13C NMR、红外光谱及质谱进行表征。

  DOI：

  10.14233/ajchem.2013.15179

文献信息

• 替格瑞洛中间体(1R,2S)-2-(2,3-二氟苯基)环 丙胺的制备方法
  申请人：成都百裕制药股份有限公司

  公开号：CN104326922B

  公开（公告）日：2016-08-17

  本发明公开了替格瑞洛中间体(1R,2S)‑2‑(2,3‑二氟苯基)环丙胺的制备方法，属于有机合成路线设计及其原料药和中间体制备技术领域，它是以丁二酸酐经醇解得丁二酸单甲酯，丁二酸单甲酯酰氯化反应得化合物丁二酸单甲酯酰氯与邻二氟苯经傅克反应得化合物4‑酮‑4‑（3,4‑二氟苯基）丁酸甲酯（Ⅳ），化合物IV再经不对称还原反应、环合反应、Hoffman降解得产物(1R,2S)‑2‑(2,3‑二氟苯基)环丙胺。该合成方法所采用的起始原料成本低，易得、反应条件温和、操作安全简便、对环境污染小，且采用该方法制备替格瑞洛关键中间体后处理简单方便，有利于大规模化生产。
• Synthesis of Novel g-Ketoesters from Succinic Anhydride
  作者：Muhammad Iqbal、Imam Bakhsh Baloch、Musa Kaleem Baloch

  DOI：10.14233/ajchem.2013.15179

  日期：——

  Four alkyl g-ketohexanoates (3a-3d) have been prepared from succinic anhydride employing a three step reaction strategy. In the first step using p-toluene sulfonic acid as catalyst, the ring of succinic anhydride was opened with isopropyl, isobutyl, isopentyl and benzyl alcohols, respectively to form alkyl hydrogen succinates (1a-1d). In the 2nd step these alkyl hydrogen succinates on treatment with SOCl2 yielded 4-alkoxy-4-ketobutanoyl chlorides (2a-2d). The acid halides thus obtained, on reaction with diethyl cadmium led to require g-ketoesters. All the synthesised compounds were characterized by recording and analyzing 1H, 13C NMR, IR spectra and mass measurements.

  四种烷基g-酮己酸酯（3a-3d）是通过三步反应策略从琥珀酸酐制备而成。在第一步中，使用对甲苯磺酸作为催化剂，分别用异丙醇、异丁醇、异戊醇和苄醇打开琥珀酸酐的环，形成烷基氢琥珀酸酯（1a-1d）。在第二步中，这些烷基氢琥珀酸酯与SOCl2处理，生成4-烷氧基-4-酮丁酰氯（2a-2d）。所获得的酸卤化物与二乙基镉反应，得到所需的g-酮酯。所有合成的化合物通过记录和分析1H和13C NMR、红外光谱及质谱进行表征。
• A Combination of Friedel-Crafts and Lawesson Reactions to 5-Substituted 2,2’-Bithiophenes
  作者：M. Manuela M. Raposo、Gilbert Kirsch

  DOI：10.3987/com-01-9249

  日期：——
• Formulating a new basis for the treatment against botulinum neurotoxin intoxication: 3,4-Diaminopyridine prodrug design and characterization
  作者：Joseph S. Zakhari、Isao Kinoyama、Mark S. Hixon、Antonia Di Mola、Daniel Globisch、Kim D. Janda

  DOI：10.1016/j.bmc.2011.09.019

  日期：2011.11

  Botulism is a disease characterized by neuromuscular paralysis and is produced from botulinum neurotoxins (BoNTs) found within the Gram positive bacterium Clostridium botulinum. This bacteria produces the most deadliest toxin known, with lethal doses as low as 1 ng/kg. Due to the relative ease of production and transport, the use of these agents as potential bioterrorist weapons has become of utmost concern. No small molecule therapies against BoNT intoxication have been approved to date. However, 3,4-diaminopyridine (3,4-DAP), a potent reversible inhibitor of voltage-gated potassium channels, is an effective cholinergic agonist used in the treatment of neuromuscular degenerative disorders that require cholinergic enhancement. 3,4-DAP has also been shown to facilitate recovery of neuromuscular action potential post botulinum intoxication by blocking K(+) channels. Unfortunately, 3,4-DAP displays toxicity largely due to blood-brain-barrier (BBB) penetration. As a dual-action prodrug approach to cholinergic enhancement we have designed carbamate and amide conjugates of 3,4-DAP. The carbamate prodrug is intended to be a slowly reversible inhibitor of acetylcholinesterase (AChE) along the lines of the stigmines thereby allowing increased persistence of released acetylcholine within the synaptic cleft. As a secondary activity, cleavage of the carbamate prodrug by AChE will afford the localized release of 3,4-DAP, which in turn, will enhance the pre-synaptic release of additional acetylcholine. Being a competitive inhibitor with respect to acetylcholine, the activity of the prodrug will be greatest at the synaptic junctions most depleted of acetylcholine. Here we report upon the synthesis and biochemical characterization of three new classes of prodrugs intended to limit previously reported stability and toxicity issues. Of the prodrugs examined, compound 32, demonstrated the most clinically relevant half-life of 2.76 h, while selectively inhibiting AChE over butyrylcholinesterase-a plasma-based high activity esterase. Future in vivo studies could provide validation of prodrug 32 as a potential treatment against BoNT intoxication as well as other neuromuscular disorders. (C) 2011 Elsevier Ltd. All rights reserved.
• Begley, Michael J.; Cameron, Andrew G.; Knight, David W., Journal of the Chemical Society. Perkin transactions I, 1986, p. 1933 - 1938
  作者：Begley, Michael J.、Cameron, Andrew G.、Knight, David W.

  DOI：——

  日期：——