ethyl 2-cyano-6-heptynoate | 91012-16-7

• 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 2-cyano-6-heptynoate
• 英文别名: (Pentin-4-yl-1)-cyanessigester；Ethyl 2-cyanohept-6-ynoate
• CAS: 91012-16-7
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: VVQKKYSTCUARAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-6-heptynoate 在 sodium hydride 作用下， 以 四氢呋喃 、 氯苯 为溶剂， 反应 36.0h， 生成 8-carbethoxy-2-(4-chlorophenyl)-8-cyano-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  1,2,4-三嗪的分子内Diels-Alder反应：利用Thorpe-Ingold效应合成2,3-环戊烯吡啶和5,6,7,8-四氢喹啉

  摘要：

  借助Thorpe-Ingold效应辅助的1,2,4-三嗪的分子内电子需求逆Diels-Alder反应已用于2,3-环戊烯吡啶和5,6,7,8-四氢喹啉的新型合成中。

  DOI：

  10.1016/s0040-4039(00)84460-3
• 作为产物：
  描述：

  氰乙酸乙酯 以49%的产率得到
  参考文献：
  名称：

  TAYLOR, EDWARD C.;MACOR, JOHN E.;FRENCH, LARRY G., J. ORG. CHEM., 56,(1991) N, C. 1807-1812

  摘要：

  DOI：

文献信息

• Macrocyclic Salen–Bis-NHC Hybrid Ligands and Their Application to the Synthesis of Enantiopure Bi- and Trimetallic Complexes
  作者：Melanie Mechler、Wolfgang Frey、René Peters

  DOI：10.1021/om500762r

  日期：2014.10.13

  Salen and NHC ligands are among the most important ligands for homogeneous catalysis. We have recently reported bimetallic complexes, in which both motifs have been merged for the first time. However, the intermetallic distances, which play a crucial role for cooperative bimetallic catalysis, were probably not appropriate in these first-generation hybrid catalysts. To generate heterobimetallic salen/NHC

  Salen和NHC配体是均相催化最重要的配体。我们最近报道了双金属配合物，其中两个基序已首次合并。但是，对于协同双金属催化作用至关重要的金属间距离可能不适用于这些第一代杂化催化剂。为了产生具有适合于协作催化的金属间距离的杂双金属salen / NHC杂化配合物，在本研究中已经制备了具有salen和两个连接的NHC供体部分的手性大环杂化配体。对于配体形成，使用手性对映体纯二胺以及手性对映体纯双咪唑，并且根据两种手性来源的构型发现匹配/不匹配的情况。有效地完成了2 O 2协调领域。随后对Ag（I），Cu（I），Au（I）和Pd（II）的NHC单元进行了配位，在后者情况下，是通过Pd 2（dba）3的氧化金属转移作用实现的。Ni / Ag 2和Pd / Ag 2配合物的X射线晶体结构分析显示，大环起伏很大，其中与NHC结合的Ag（I）中心之一紧邻与salen结合的Ni（II）或Pd。 （II）中
• Palladium(II)-catalyzed coupling reactions of alkynes and allylic compounds initiated by intramolecular carbopalladation of alkynes
  作者：Guosheng Liu、Xiyan Lu

  DOI：10.1016/s0040-4039(02)01512-5

  日期：2002.9

  Under divalent palladium catalysis, a highly regio- and stereoselective coupling reaction of alkynes with allyl halides initiated by cyclocarbopalladation of alkynes proceeded smoothly in the presence of excess halide ions. The reaction involves intramolecular carbopalladation, allylic compound insertion into the vinylicPd bond and quenching the CPd bond by β-heteroatom elimination in one step without

  在二价钯催化下，炔烃与炔烃的环碳烷基缩合引发的烯丙基卤化物的高度区域选择性和立体选择性偶合反应在过量卤化物离子存在下顺利进行。该反应涉及分子内碳氢合反应，将烯丙基化合物插入乙烯基Pd键中以及通过不使用氧化剂的β-杂原子消除一步淬灭CPd键。
• Intramolecular Diels-Alder reactions of 1,2,4-triazines. Synthesis of 2,3-cyclopentenopyridines and 5,6,7,8-tetrahydroquinolines
  作者：Edward C. Taylor、John E. Macor、Larry G. French

  DOI：10.1021/jo00005a027

  日期：1991.3

  2,3-Cyclopentenopyridines and 5,6,7,8-tetrahydroquinolines are prepared by intramolecular Diels-Alder reactions of appropriately substituted 1,2,4-triazines. Two general routes to the requisite triazine precursors are described.
• Julia,M.; James,C., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1962, vol. 255, p. 959 - 960
  作者：Julia,M.、James,C.

  DOI：——

  日期：——
• Intramolecular and Intermolecular Mn(III)-Induced Carbon Monoxide Trapping Reactions of Alkynes with Malonate and Cyano Ester Units
  作者：Kazumi Okuro、Howard Alper

  DOI：10.1021/jo9607673

  日期：1996.1.1

  Intra- and intermolecular carbon monoxide trapping reactions of alkynes with malonates and cyano esters were developed using a Mn(III)-induced oxidative system. Phenylacetylene was treated with diethyl ethylmalonate in the presence of Mn(OAc)(3) . 2H(2)O, in AcOH-CH3CN (1:1) under carbon monoxide, affording (Z)-4,4-dicarbethoxy-2-phenyl-2-hexenoic acid. Similarly, intramolecular reactions of 4-alkynylmalonates and cyanoacetates proceeded regio- and stereoselectively under the same conditions to afford the corresponding methylenecycloalkanecarboxylic acids in moderate yields. The reaction involves carbon monoxide trapping of vinyl radicals which are formed by the addition of malonate or cyanoacetate radicals induced by Mn(III) to alkynes.