2-hex-5-enylmalonic acid | 90613-10-8

• 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: 2-hex-5-enylmalonic acid
• 英文别名: 2-Hex-5-enylpropanedioic acid
• CAS: 90613-10-8
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: HNAWGPAYWBSVRF-UHFFFAOYSA-N

物化性质

• 熔点：
  73 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  371.7±42.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hex-5-enylmalonic acid 在 硫酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.17h， 生成 7-辛烯酸,甲基酯
  参考文献：
  名称：

  Divinylcarbinol的不对称化策略：手性羟基化脂肪酸衍生物的一种可靠的可靠方法

  摘要：

  借助于二乙烯基甲醇的催化去对称化作为一锅不对称诱导和保护烯烃，成功地实现了两种手性羟基化脂肪酸衍生物的不对称全合成。可以在温和条件下以高度收敛的方式简明地制备所需的立体异构体。因此，这种新颖的策略可以帮助对天然产物进行立体化学阐明，由于其在立体生成的仲羟基单元附近的局部对称性，在光谱立体化学分析中存在困难。

  DOI：

  10.1021/acs.joc.0c02821
• 作为产物：
  描述：

  hex-5-enyl 4-methylbenzenesulfonate 在 lithium hydroxide monohydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 2-hex-5-enylmalonic acid
  参考文献：
  名称：

  Divinylcarbinol的不对称化策略：手性羟基化脂肪酸衍生物的一种可靠的可靠方法

  摘要：

  借助于二乙烯基甲醇的催化去对称化作为一锅不对称诱导和保护烯烃，成功地实现了两种手性羟基化脂肪酸衍生物的不对称全合成。可以在温和条件下以高度收敛的方式简明地制备所需的立体异构体。因此，这种新颖的策略可以帮助对天然产物进行立体化学阐明，由于其在立体生成的仲羟基单元附近的局部对称性，在光谱立体化学分析中存在困难。

  DOI：

  10.1021/acs.joc.0c02821

文献信息

• Heterocyclic compounds
  申请人：——

  公开号：US20030166697A1

  公开（公告）日：2003-09-04

  The present invention provides a preventive or therapeutic agent for hyperlipidemia, comprising as an active ingredient a heterocyclic compound of the formula [1], or a pharmaceutically acceptable salt thereof: R 1 -Het-D-E  [1] wherein: R 1 is optionally substituted aryl or aromatic heterocyclic group, Het is a divalent aromatic heterocyclic group, D is alkylene, alkenylene, alkynylene, or the like, and E is carboxy, or the like, and novel compounds among the heterocyclic compounds of the formula [1] above, which has blood triglyceride lowering effect, LDL-C lowering effect, and blood glucose lowering effect and blood insulin lowering effect, or HDL-C increasing effect or atherogenic index lowering effect all together, and hence is useful in the prevention or treatment of hyperlipidemia, arteriosclerosis, diabetes mellitus, hypertension, obesity, and the like.

  本发明提供了一种用于高脂血症的预防或治疗剂，其活性成分为式[1]所示的杂环化合物或其药学上可接受的盐：R1-Het-D-E [1]其中：R1为任选取代的芳基或芳香性杂环基团，Het为二价芳香性杂环基团，D为亚烷基、亚烯基、亚炔基等，E为羧基等，以及上述式[1]所示杂环化合物中的新型化合物，其具有降低血液甘油三酯、降低LDL-C、降低血糖、降低血液胰岛素、增加HDL-C或降低动脉粥样硬化指数的效果，因此可用于预防或治疗高脂血症、动脉硬化、糖尿病、高血压、肥胖等疾病。
• On the Intramolecular 1,4-Dipolar Cycloaddition Reaction of Thiazinium Betaines for the Construction of Aza-, Diaza-, and Polyaza-Heterocyclic Ring Systems
  作者：Albert Padwa、Steven J. Coats、Scott R. Harring、Lazaros Hadjiarapoglou、Mark A. Semones

  DOI：10.1055/s-1995-4032

  日期：1995.8

  A series of bicyclic anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides containing tethered π-systems are easily prepared from the reaction of thiolactams with 1,3-bielectrophiles. These cross-conjugated heteroaromatic betaines undergo regio- and stereospecific 1,4-dipolar cycloaddition in good yield to produce cycloadducts containing a carbonyl sulfide bridge which can be induced to lose COS on further heating. Two of the cycloadducts were characterized by single crystal X-ray determinations. Control of ring size in the final product of the cycloaddition can be achieved by variation of the dipolarophilic chain length. Entry to the [6,6,5]- and [6,6,6]pyridone ring systems was possible using phenylalkynyl-substituted thioamides. Intramolecular 1,4-dipolar cycloaddition of a thiazinium betaine dipole also occurs across an indolyl π-bond. With only one substituent group in the 9-position of the bicyclic betaine, the reaction takes an entirely different course unless a highly activated π-bond is incorporated into the tether. The preferred reaction with modestly activated π-systems corresponds to loss of the activated proton to produce an S,N-ketene acetal. When a ketene S,S-acetal group was incorporated onto the side chain, the 1,4-dipolar cycloaddition reaction was facilitated relative to proton loss.

  一系列含有联接π系统的双环无水-4-羟基-2-氧-1,3-噻唑鎓氢氧化物可以通过硫内酰胺与1,3-双电亲体的反应轻松制备。这些交错共轭的杂芳香族贝塔因在良好的产率下经历区域性和立体特异性的1,4-偶极环加成，生成含有羰基硫桥的环加成物，在进一步加热时可以诱导失去COS。通过单晶X射线测定对其中两个环加成物进行了表征。通过改变偶极亲核链的长度，可以控制环加成反应最终产物的环大小。使用苯基炔基取代的硫氨基可以实现对[6,6,5]-和[6,6,6]吡啶酮环系的导入。噻唑鎓贝塔因偶极的环内1,4-偶极环加成也发生在吲哚的π键上。在双环贝塔因的9位仅有一个取代基时，反应的路径会完全不同，除非在连结中加入一个高度活化的π键。与适度活化的π系统的优选反应对应于活化质子的失去，从而生成S,N-烯酮缩醛。当在侧链上引入烯酮S,S-缩醛基时，相较于质子失去，1,4-偶极环加成反应得以促进。
• HETEROCYCLIC COMPOUNDS
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP1295875A1

  公开（公告）日：2003-03-26

  The present invention provides a preventive or therapeutic agent for hyperlipidemia, comprising as an active ingredient a heterocyclic compound of the formula [1] or a pharmaceutically acceptable salt thereof:         R1―Het―D―E     [1] wherein: R1 is optionally substituted aryl or aromatic heterocyclic group, Het is a divalent aromatic heterocyclic group, D is alkylene, alkenylene, alkynylene, or the like, and E is carboxy, or the like, and novel compounds among the heterocyclic compounds of the formula [1] above, which has blood triglyceride lowering effect, LDL-C lowering effect, and blood glucose lowering effect and blood insulin lowering effect, or HDL-C increasing effect or atherogenic index lowering effect all together, and hence is useful in the prevention or treatment of hyperlipidemia, arteriosclerosis, diabetes mellitus, hypertension, obesity, and the like.

  本发明提供了一种预防或治疗高脂血症的药物，其活性成分包括式 [1] 的杂环化合物或其药学上可接受的盐： R1-Het-D-E [1] 其中 R1为任选取代的芳基或芳香杂环基团，Het为二价芳香杂环基团，D为亚烷基、亚烯基、亚炔基或类似基团，E为羧基或类似基团，上述式[1]杂环化合物中的新型化合物，具有降血甘油三酯作用、低密度脂蛋白胆固醇（LDL-C）降低效果、血糖降低效果和血胰岛素降低效果，或高密度脂蛋白胆固醇（HDL-C）增加效果或动脉粥样硬化指数降低效果，因此可用于预防或治疗高脂血症、动脉硬化、糖尿病、高血压、肥胖症等。
• Heterocyclic compounds for the treatment of hyperlipidemia agents
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP1634876A2

  公开（公告）日：2006-03-15

  The present invention provides a preventive or therapeutic agent for hyperlipidemia, comprising as an active ingredient a heterocyclic compound of the formula [1] or a pharmaceutically acceptable salt thereof:         R 1 -Het-D-E     [1] The preventive or therapeutic agent has a blood triglyceride lowering effect, LDL-C lowering effect, and blood glucose lowering effect and blood insulin lowering effect, or HDL-C increasing effect or atherogenic index lowering effect all together, and hence is useful in the prevention or treatment of hyperlipidemia, arteriosclerosis, diabetes mellitus, hypertension, obesity, and the like.

  本发明提供了一种预防或治疗高脂血症的药物，其活性成分包括式 [1] 的杂环化合物或其药学上可接受的盐： R 1 -Het-D-E [1] 该预防或治疗剂具有降血甘油三酯作用、降低密度脂蛋白胆固醇作用、降血糖作用和降血胰岛素作用，或增加高密度脂蛋白胆固醇作用或降低动脉粥样硬化指数作用，因此可用于预防或治疗高脂血症、动脉硬化、糖尿病、高血压、肥胖症等。
• Biosynthetic Precursors of the Lipase Inhibitor Lipstatin
  作者：Christoph A. Schuhr、Wolfgang Eisenreich、Markus Goese、Peter Stohler、Wolfgang Weber、Ernst Kupfer、Adelbert Bacher

  DOI：10.1021/jo016285v

  日期：2002.4.1

  Three putative intermediates in the biosynthesis of the lipase inhibitor lipstatin were synthesized in stable isotope-labeled form and were added to fermentation cultures of Streptomyces toxytricini. Biosynthetic lipstatin was isolated and analyzed by NMR spectroscopy. [3,10,11,12-H-2]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor of lipstatin. [7,8-H-2(2)]Hexylmalonate (11) was also incorporated into lipstatin, albeit at a relatively low rate. The leucine moiety of [C-13-formyl,N-15]-N-formylleucine (10) was diverted to lipstatin under loss of the C-13-labeled formyl residue.