perfluorophenyl-2-oxoacetyl chloride | 1149343-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: perfluorophenyl-2-oxoacetyl chloride
• 英文别名: pentafluorophenylglyoxyl chloride；2-Oxo-2-(2,3,4,5,6-pentafluorophenyl)acetyl chloride
• CAS: 1149343-32-7
• 化学式: C₈ClF₅O₂
• 分子量: 258.532
• InChiKey: OHAAUPKOYGHFEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  perfluorophenyl-2-oxoacetyl chloride 、 三丁基苯基锡 以 甲苯 为溶剂， 反应 3.0h， 以98%的产率得到1-(perfluorophenyl)-2-phenylethane-1,2-dione
  参考文献：
  名称：

  α-氧代酰氯或草酰氯与有机锡烷烃的无过渡金属-催化剂反应合成1,2-二酮

  摘要：

  α-氧代酰氯与有机锡烷的反应可进行无过渡金属催化剂的处理，从而以极好的收率得到1,2-二酮。另外，包括用有机锡烷预处理草酰氯和随后用另一种有机锡烷进行后续处理的顺序也可作为方便的修饰。

  DOI：

  10.1021/jo802814r
• 作为产物：
  描述：

  (pentafluorophenyl)glyoxylic acid 在 1,1-二氯甲醚 作用下， 反应 3.25h， 以49.7%的产率得到perfluorophenyl-2-oxoacetyl chloride
  参考文献：
  名称：

  α-氧代酰氯或草酰氯与有机锡烷烃的无过渡金属-催化剂反应合成1,2-二酮

  摘要：

  α-氧代酰氯与有机锡烷的反应可进行无过渡金属催化剂的处理，从而以极好的收率得到1,2-二酮。另外，包括用有机锡烷预处理草酰氯和随后用另一种有机锡烷进行后续处理的顺序也可作为方便的修饰。

  DOI：

  10.1021/jo802814r

文献信息

• Rhodium-Catalyzed Addition of α-Keto Acid Chlorides with Terminal Alkynes
  作者：Taigo Kashiwabara、Masato Tanaka

  DOI：10.1002/adsc.201100108

  日期：2011.6

  The addition reaction of α‐keto acid chlorides with terminal alkynes proceeds in the presence of (acetylacetonato)dicarbonylrhodium used as catalyst to afford synthetically versatile (Z)‐γ‐chloro‐α‐oxo‐β,γ‐unsaturated ketones regio‐ and stereoselectively.

  α-酮酰氯与末端炔烃的加成反应在（乙酰丙酮基）二羰基铑存在下进行，以提供合成用途广泛的（Z）-γ-氯-α-氧代-β，γ-不饱和酮区域和立体选择性。
• Arylglyoxylrhodium Complexes, Their Thermolysis, and Attempted Generation by Carbonylation of an Aroylrhodium Complex
  作者：Taigo Kashiwabara、Masato Tanaka

  DOI：10.1021/om101079e

  日期：2011.1.24

  Reactions of ArCOCOCl (Ar = p-ClC(6)H(4), Ph) with Rh(acac)(CO)(2) proceeded readily to afford dimeric arylglyoxyl rhodium complexes [Rh(mu-Cl)(acac)(CO)(COCOAr)](2). [Rh(mu-Cl)(acac)(CO)COCO(p-ClC(6)H(4))}](2) was characterized by X-ray diffraction. Thermolysis of the products showed that [Rh(mu-Cl)(acac)(CO)COCO(p-ClC(6)H(4))}](2) was more stable than [Rh(mu-Cl)(acac)(CO)(COCOPh)](2). The reaction of p-CH(3)OC(6)H(4)COCOCl with Rh(acac)(CO)(2) did not form a similar dimeric complex as final product, but gave p-CH(3)OC(6)H(4)COCl as major product, showing thermal instability of corresponding arylglyoxyl and aroyl rhodium complexes. The reaction of C(6)F(5)CO-COCl did not form a simlar dimeric complex either, but a mononuclear complex RhCl(acac)(COCOC(6)F(5))(CO)(2) was generated as a transient intermediate, which was readily transformed to a furanone arising from reductive elimination of the acac ligand and C(6)F(5)COCO moiety followed by cyclization. In the thermolysis of [Rh(mu-Cl)(acac)(CO)(COCOAr)](2), only ArCOCl and Rh(acac)(CO)(2) were formed, and any ArCORh species could not be detected during the thermolysis process. However, the reaction of Rh(acac)(CO)(2) with PhCOCl formed RhCl(acac)(CO)(2)(COPh), albeit only to a small extent, suggesting that the reaction is not thermodynamically favored. The reaction of RhCl(CO)(PMe(3))(2) with p-ClC(6)H(4)COCOCl also proceeded cleanly to furnish p-ClC(6)H(4)COCORhCl(2)(CO)(PMe(3))(2). Thermolysis of the complex formed p-ClC(6)H(4)CORhCl(2)(CO)(PMe(3))(2), indicating slow reductive elimination of ClC(6)H(4)COCl as compared with the ArCORh species, generated in the thermolysis of [Rh(mu-Cl)(acac)(CO)(COCOAr)](2). Treatment of ClC(6)H(4)CORhCl(2)(CO)(PMe(3))(2) with carbon monoxide generates p-ClC(6)H(4)COCORhCl(2)(CO)(PMe(3))(2), although the yield was low.
• Synthesis of 1,2-Diketones by the Transition Metal-Catalyst-Free Reaction of α-Oxo Acid Chlorides or Oxalyl Chloride with Organostannanes
  作者：Taigo Kashiwabara、Masato Tanaka

  DOI：10.1021/jo802814r

  日期：2009.5.15

  The reaction of an α-oxo acid chloride with an organostannane proceeds transition metal-catalyst-free to afford a 1,2-diketone in an excellent yield. In addition, a sequence comprising pretreatment of oxalyl chloride with an organostannane and a subsequent treatment with another organostannane also works as a convenient modification.

  α-氧代酰氯与有机锡烷的反应可进行无过渡金属催化剂的处理，从而以极好的收率得到1,2-二酮。另外，包括用有机锡烷预处理草酰氯和随后用另一种有机锡烷进行后续处理的顺序也可作为方便的修饰。