1-(1-辛炔基)-1-环戊烯 | 58149-18-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 1-(1-辛炔基)-1-环戊烯
• 英文名称: 1-(1-octynyl)-1-cyclopentene
• 英文别名: 1-(1-cyclopentenyl)octyne；1-(1-octynyl)cyclopentene；1-Octin-1-yl-1-cyclopenten；1-(1-Octinyl)-cyclopenten；1-Oct-1-ynylcyclopentene
• CAS: 58149-18-1
• 化学式: C₁₃H₂₀
• 分子量: 176.302
• InChiKey: MPOICCDRLLYVNN-UHFFFAOYSA-N

物化性质

• 沸点：
  70-75 °C(Press: 0.1 Torr)
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(1-辛炔基)-1-环戊烯 在 甲酸 、 双氧水 作用下， 生成 6-oxo-tridecanoic acid
  参考文献：
  名称：

  Untersuchungen �ber die Bildung von 2-Acylcyclopentanonen aus 1-(1-�thynyl)-cyclopentenen und Perameisens�ure

  摘要：

  DOI：

  10.1007/bf01153928
• 作为产物：
  描述：

  1-辛炔 在 吡啶 、 三氯氧磷 作用下， 生成 1-(1-辛炔基)-1-环戊烯
  参考文献：
  名称：

  Untersuchungen über Synthesewege zu 2-Äthynyl-2-cyclopenten-1-onen

  摘要：

  DOI：

  10.1007/bf00906235

文献信息

• Palladium-catalyzed hydrogenolysis of 2-alkynyl formates and elimination of 2-alkynyl carbonates. 2-Alkynylpalladium complex vs. allenylpalladium complex as intermediates
  作者：Tadakatsu Mandai、Takaji Matsumoto、Yoshikazu Tsujiguchi、Shin Matsuoka、Jiro Tsuji

  DOI：10.1016/0022-328x(94)80136-3

  日期：1994.6

  Examples of palladium-catalyzed reactions of 2-alkynyl esters via the 2-alkynylpalladium intermediates are presented. The palladium-catalyzed hydrogenolysis of 2-alkynyl formates, which have internal triple bonds, affords alkynes via the 2-alkynylpalladium as an intermediate. The elimination reaction of 2-alkynyl carbonates yields conjugated enynes via the 2-alkynylpalladium intermediates.

  给出了经由2-炔基钯中间体的钯催化的2-炔基酯反应的实例。2-炔基甲酸盐，其具有内部三键，得到炔烃钯催化氢解通过2- alkynylpalladium作为中间体。2-炔基碳酸酯的产率的消除反应共轭烯炔经由2- alkynylpalladium中间体。
• Cobalt-catalyzed cross-coupling of alkynyl Grignard reagents with alkenyl triflates
  作者：Eiji Shirakawa、Takahiro Sato、Yusuke Imazaki、Takahiro Kimura、Tamio Hayashi

  DOI：10.1039/b711884h

  日期：——

  Alkenyl triflates in combination with Co(acac)(3) as a catalyst were found to be excellent coupling partners of alkynyl Grignard reagents, where no special additives (even a phosphine ligand) but a common solvent, THF, are required to obtain variously substituted enynes.

  发现链烯基三氟甲磺酸酯与Co（acac）（3）组合作为催化剂是炔基格利雅试剂的极佳偶联伙伴，不需要特殊添加剂（甚至是膦配体），而只需使用普通溶剂THF即可获得各种取代基恩尼斯。
• Preparation of conjugated enynes by the palladium-catalyzed elimination reaction of propargylic carbonates
  作者：Tadakatsu Mandai、Yoshikazu Tsujiguchi、Shin Matsuoka、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)60414-8

  日期：1993.11

  Propargylic carbonates are cleanly converted to conjugated enynes by palladium-catalyzed elimination reaction under mild and neutral conditions.

  在温和和中性条件下，通过钯催化的消除反应，丙炔基碳酸酯可干净地转化为共轭烯炔。
• Silver(I)-Catalyzed Cascade: Direct Access to Furans from Alkynyloxiranes
  作者：Aurélien Blanc、Katharina Tenbrink、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo900483m

  日期：2009.6.5

  Functionalized furans are conveniently formed by a new silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol. Evidence supported a cascade mechanism.
• Mechanistic Studies and Improvement of Coinage Metal-Catalyzed Transformation of Alkynyloxiranes to Furans: An Alcohol Addition−Cyclization−Elimination Cascade
  作者：Aurélien Blanc、Katharina Tenbrink、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo9008172

  日期：2009.8.7

  In the presence of alcohol Ag or Au salts or complexes catalyze the conversion of alkynyloxiranes to substituted furans. Both-catalysts are effective, and a large furan diversity can be obtained in high yield with one or the other catalyst. Mechanistic studies revealed that a cascade pathway and not the sometimes reported direct intra molecular nucleophilic addition of oxirane oxygen atom to intermediate acetylene-metal pi-complex occurs. Under the defined conditions, the intermediate formation of epoxide opening products has been identified. Depending on the catalyst, one or both of the latter cyclized to dihydrofurans, and further elimination of the alcohol led to the corresponding furans. These results highlight the duality between oxophilicity and alkynophilicity of Ag or Au salts.