2-but-2-ynyl-hex-4-ynoic acid methyl ester

• 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-but-2-ynyl-hex-4-ynoic acid methyl ester
• 英文别名: methyl 2-(but-2-yn-1-yl)hex-4-ynoate；Methyl 2-but-2-ynylhex-4-ynoate；methyl 2-but-2-ynylhex-4-ynoate
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: BVVUFFYEBSFSKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  2-but-2-ynyl-hex-4-ynoic acid methyl ester 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到2-(but-2-yn-1-yl)hex-4-ynoic acid
  参考文献：
  名称：

  Enantioselective, Desymmetrizing Bromolactonization of Alkynes

  摘要：

  Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD)(2)PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter are valuable building blocks for synthetic chemistry.

  DOI：

  10.1021/ja402910d
• 作为产物：
  描述：

  dimethyl 2,2-di(but-2-yn-1-yl)malonate 在 palladium diacetate 一氧化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 2-but-2-ynyl-hex-4-ynoic acid methyl ester
  参考文献：
  名称：

  钯催化的 [2 + 2 + 1] 分子内环加成用于从 1,6-二炔制备双环 [3.3.0]octa-1.5-dien-3-ones 可用电子补充信息 (ESI)：实验。见 http://www.rsc.org/suppdata/cc/b3/b302841k/

  摘要：

  钯催化的 1,6-庚二炔与 CO (1 atm) 的 [2 + 2 + 1] 环加成以 30-74% 的产率提供双环 [3.3.0]octa-1,5-dien-3-one。

  DOI：

  10.1039/b302841k

文献信息

• Palladium catalysed [2 + 2 + 1] intramolecular cycloaddition for the preparation of bicyclo[3.3.0]octa-1.5-dien-3-ones from 1,6-diynesElectronic supplementary information (ESI) available: experimental. See http://www.rsc.org/suppdata/cc/b3/b302841k/
  作者：Ronald Grigg、Lixin Zhang、Simon Collard、Ann Keep

  DOI：10.1039/b302841k

  日期：——

  Palladium catalysed [2 + 2 + 1] cycloaddition of 1,6-heptadiynes with CO (1 atm) furnishes bicyclo[3.3.0]octa-1,5-dien-3-ones in 30-74% yield.

  钯催化的 1,6-庚二炔与 CO (1 atm) 的 [2 + 2 + 1] 环加成以 30-74% 的产率提供双环 [3.3.0]octa-1,5-dien-3-one。
• Efficient Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of CO₂ and Diynes
  作者：Janis Louie、John E. Gibby、Marc V. Farnworth、Thomas N. Tekavec

  DOI：10.1021/ja027438e

  日期：2002.12.1

  A mild and general route for preparing 2-pyrones from CO2 and diynes is described. Under only 1 atm of CO2, excellent yields of pyrone are obtained using catalytic amounts of Ni(COD)2 and imidazolylidene ligand, IPr. In addition, stoichiometric reactions between the isolated complex Ni(IPr)2, diynes, and CO2 suggest that the pathway involves initial reaction with CO2 as the key step.
• Rhodium-Catalyzed Decarboxylative Cycloaddition Route to Substituted Anilines
  作者：Kainan Zhang、Janis Louie

  DOI：10.1021/jo200236h

  日期：2011.6.3

  A convenient method for preparing substituted anilines via a Rh-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and 2-oxazolone was discovered. The initial cycloaddition adducts undergo facile decarboxylation of carbon dioxide to afford aniline products. Reaction conditions are mild, and only 3 mol % Rh catalyst is required. High regioselectivity was observed when an unsymmetrical diyne was used as a starting material.
• Enantioselective, Desymmetrizing Bromolactonization of Alkynes
  作者：Michael Wilking、Christian Mück-Lichtenfeld、Constantin G. Daniliuc、Ulrich Hennecke

  DOI：10.1021/ja402910d

  日期：2013.6.5

  Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD)(2)PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter are valuable building blocks for synthetic chemistry.