4-(3-oxo-1-cyclohexenyl)-coumarin | 134817-32-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(3-oxo-1-cyclohexenyl)-coumarin
• 英文别名: 4-(3-Oxocyclohexen-1-yl)chromen-2-one
• CAS: 134817-32-6
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: IYDAMJBJKLQZQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-Iodocyclohex-2-enone 、 在 二甲基硫 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以70%的产率得到4-(3-oxo-1-cyclohexenyl)-coumarin
  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

• A direct preparation of vinylogous acyl anion equivalents
  作者：C. Janakiram Rao、Paul Knochel

  DOI：10.1021/jo00015a004

  日期：1991.7

  Unmasked vinylogous acyl anion equivalents 2 were prepared by the insertion of zinc to various beta-halo, alpha,beta-unsaturated ketones and esters 1. The new reagents 2 react with various electrophiles in the presence of CuCN.2LiCl or catalytic amounts of Pd(0) complexes in excellent yields.
• RAO, C. JANAKIRAM;KNOCHEL, PAUL, J. ORG. CHEM., 56,(1991) N5, C. 4593-4596
  作者：RAO, C. JANAKIRAM、KNOCHEL, PAUL

  DOI：——

  日期：——
• 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.