(E)-1-octenyl-2-cyclohexen-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-octenyl-2-cyclohexen-1-one
• 英文别名: 3-[(1E)-1-octenyl]-2-cyclohexen-1-one；3-[(E)-oct-1-enyl]cyclohex-2-en-1-one
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: VSKPYAWRLWIVDZ-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  反式-BETA-苯乙烯硼酸 、 (E)-1-octenyl-2-cyclohexen-1-one 在 bis(1,5-cyclooctadiene)nickel (0) 、 水 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以63%的产率得到3-((E)-oct-1-en-1-yl)-3-((E)-styryl)cyclohexan-1-one
  参考文献：
  名称：

  Alkene-Assisted Nickel-Catalyzed Regioselective 1,4-Addition of Organoboronic Acid to Dienones: A Direct Route to All-Carbon Quaternary Centers

  摘要：

  A nickel-catalyzed highly regioselective 1,4-addition reaction of boronic acids to dienones to form products with an all-carbon quaternary center is described. The 3-alkenyl group of dienones is the key for the reaction to proceed smoothly. A mechanism involving the coordination of the dienyl group to the nickel center is proposed.

  DOI：

  10.1021/ol500838h
• 作为产物：
  描述：

  反式-1-碘-1-辛烯 、 3-oxo-1-cyclohexen-1-ylzinc iodide 在 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以73%的产率得到(E)-1-octenyl-2-cyclohexen-1-one
  参考文献：
  名称：

  官能化烯基锌，铜和铬有机金属化合物的制备和反应性

  摘要：

  Beta-halogeno-alpha,beta-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45-degrees-C, 1-4h). These functionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97% yield. The addition of a THF solution of CuCN.2LiCl to 2a affords the corresponding organocopper derivatives 2b which react with electrophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfunctional unsaturated carbonyl compounds in 71-95% yield. The insertion of chromium (II) chloride to beta-iodo and to some beta-(p-tosyl)enones in DMF furnishes new functionalized chromium (III) organometallics 2c which react with aldehydes providing gamma-hydroxy unsaturated carbonyl derivatives in 40-91% yield. The synthetic scope and the limitations of this methodology are discussed.

  DOI：

  10.1016/s0040-4020(01)80504-4

文献信息

• US5166382A
  申请人：——

  公开号：US5166382A

  公开（公告）日：1992-11-24
• Preparation and reactivity of functionalized alkenyl-zinc, -copper, and -chromium organometallics
  作者：Paul Knochel、C. Janakiram Rao

  DOI：10.1016/s0040-4020(01)80504-4

  日期：1993.1

  Beta-halogeno-alpha,beta-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45-degrees-C, 1-4h). These functionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97% yield. The addition of a THF solution of CuCN.2LiCl to 2a affords the corresponding organocopper derivatives 2b which react with electrophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfunctional unsaturated carbonyl compounds in 71-95% yield. The insertion of chromium (II) chloride to beta-iodo and to some beta-(p-tosyl)enones in DMF furnishes new functionalized chromium (III) organometallics 2c which react with aldehydes providing gamma-hydroxy unsaturated carbonyl derivatives in 40-91% yield. The synthetic scope and the limitations of this methodology are discussed.
• Alkene-Assisted Nickel-Catalyzed Regioselective 1,4-Addition of Organoboronic Acid to Dienones: A Direct Route to All-Carbon Quaternary Centers
  作者：Ya-Chun Hong、Parthasarathy Gandeepan、Subramaniyan Mannathan、Wei-Tse Lee、Chien-Hong Cheng

  DOI：10.1021/ol500838h

  日期：2014.6.6

  A nickel-catalyzed highly regioselective 1,4-addition reaction of boronic acids to dienones to form products with an all-carbon quaternary center is described. The 3-alkenyl group of dienones is the key for the reaction to proceed smoothly. A mechanism involving the coordination of the dienyl group to the nickel center is proposed.