ethyl dodec-5-ynoate | 126761-04-4

• 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 dodec-5-ynoate
• 英文别名: ethyl 5-dodecynoate
• CAS: 126761-04-4
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: IMSLYDCZUITFJP-UHFFFAOYSA-N

物化性质

• 沸点：
  301.6±25.0 °C(Predicted)
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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 dodec-5-ynoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以97%的产率得到十二碳-5-炔-1-醇
  参考文献：
  名称：

  Synthesis and Stereochemistry-Activity Relationship of small Bacteriocin, an Autoinducer of the Symbiotic Nitrogen-Fixing Bacterium Rhizobium leguminosarum

  摘要：

  The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3'-hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of R. leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.

  DOI：

  10.1021/ol8005198
• 作为产物：
  描述：

  diethyl 4-decynoylmalonate 在 水 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 7.0h， 以76%的产率得到ethyl dodec-5-ynoate
  参考文献：
  名称：

  Synthesis and Stereochemistry-Activity Relationship of small Bacteriocin, an Autoinducer of the Symbiotic Nitrogen-Fixing Bacterium Rhizobium leguminosarum

  摘要：

  The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3'-hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of R. leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.

  DOI：

  10.1021/ol8005198

文献信息

• Transition metal complexes of N-heterocyclic carbenes, method of preparation and use in transition metal catalyzed organic transformations
  申请人：Organ G. Michael

  公开号：US20070073055A1

  公开（公告）日：2007-03-29

  The present invention relates to catalysts of transition metal complexes of N-heterocyclic carbenes, their methods of preparation and their use in chemical synthesis. The synthesis, ease-of-use, and activity of the compounds of the present invention are substantial improvements over in situ catalyst generation. Further, the transition metal complexes of N-heterocyclic carbenes of the present invention may be used as precatalysts in metal-catalyzed cross-coupling reactions.

  本发明涉及N-杂环卡宾的过渡金属配合物催化剂，其制备方法以及它们在化学合成中的应用。本发明化合物的合成、易用性和活性明显优于原位催化剂生成。此外，本发明的N-杂环卡宾的过渡金属配合物可以作为金属催化的交叉偶联反应中的预催化剂。
• Ni-Catalyzed Sonogashira Coupling of Nonactivated Alkyl Halides: Orthogonal Functionalization of Alkyl Iodides, Bromides, and Chlorides
  作者：Oleg Vechorkin、Delphine Barmaz、Valérie Proust、Xile Hu

  DOI：10.1021/ja906040t

  日期：2009.9.2

  Ni-catalyzed Sonogashira coupling of nonactivated, beta-H-containing alkyl halides, including chlorides, is reported. The coupling is tolerant to a wide range of functional groups, including ether, ester, amide, nitrile, keto, heterocycle, acetal, and aryl halide, in both coupling partners. The coupling can be selective for a specific C-X bond (X = I, Br, Cl) and allows for orthogonal functionalization

  据报道，Ni 催化的 Sonogashira 偶联未活化的、含 β-H 的烷基卤化物，包括氯化物。偶联可以耐受多种官能团，包括醚、酯、酰胺、腈、酮、杂环、乙缩醛和芳基卤化物，在两种偶联伙伴中。偶联可以对特定的 CX 键 (X = I, Br, Cl) 具有选择性，并允许具有多个反应位点的卤代烷正交官能化。
• The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters
  作者：Ming Chang P. Yeh、Paul Knochel

  DOI：10.1016/s0040-4039(01)80511-6

  日期：1989.1

  The highly functionalized organometallics RCu(CN)ZnI 1 react efficiently with 1-haloalkynes providing polyfunctionalized alkynes in high yields. This method has been used to prepare a pheromone of the Amathes c-nigrum in 3 steps and 64% overall yield. The reagents 1 also add in the presence of an excess of Me3SiCl to acetylenic esters to afford polyfunctionalized C—silylated ethylenic esters. In the

  高度官能化的有机金属化合物RCu（CN）ZnI 1与1-卤代炔烃有效反应，从而以高收率提供多官能团炔烃。该方法已被用于分3步制备Amathes c-igigrum的信息素，总产率为64％。试剂1还在过量的Me 3 SiCl存在下添加至炔属酯中，以提供多官能化的C-甲硅烷基化的烯属酯。在丙酸乙酯的情况下，该反应是高度立体选择性的，并提供97％纯的（E）-2-三甲基甲硅烷基乙烯酯。
• US7250510B2
  申请人：——

  公开号：US7250510B2

  公开（公告）日：2007-07-31
• Synthesis and Stereochemistry-Activity Relationship of <i>small</i> Bacteriocin, an Autoinducer of the Symbiotic Nitrogen-Fixing Bacterium <i>Rhizobium leguminosarum</i>
  作者：Arata Yajima、Anton A. N. van Brussel、Jan Schripsema、Tomoo Nukada、Goro Yabuta

  DOI：10.1021/ol8005198

  日期：2008.5.1

  The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3'-hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of R. leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.