1-diazo-1-(3,5-dimethylphenylsulfonyl)-5-hexen-2-one | 923001-88-1

• 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: 1-diazo-1-(3,5-dimethylphenylsulfonyl)-5-hexen-2-one
• 英文别名: 1-Diazonio-1-(3,5-dimethylbenzene-1-sulfonyl)hexa-1,5-dien-2-olate；1-diazo-1-(3,5-dimethylphenyl)sulfonylhex-5-en-2-one
• CAS: 923001-88-1
• 化学式: C₁₄H₁₆N₂O₃S
• 分子量: 292.359
• InChiKey: PDXMSZKZFYSHRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-diazo-1-(3,5-dimethylphenylsulfonyl)-5-hexen-2-one 在 (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole] 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 16.0h， 生成 [(1R,2R)-2-(3,5-Dimethyl-benzenesulfonyl)-3-oxo-cyclopentyl]-acetonitrile
  参考文献：
  名称：

  Studies on the structure–enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group

  摘要：

  This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of alpha-diazo-beta-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the alpha-diazo-beta-keto sulfones was varied by the position of a methyl group on the pheny] group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95% yield with 93% ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened P-keto sulfone derivative 15h provides the C-alkylated product as a major product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.046
• 作为产物：
  描述：

  1,3-dimethyl-5-(methylsulfonyl)benzene 在 正丁基锂 、 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 10.5h， 生成 1-diazo-1-(3,5-dimethylphenylsulfonyl)-5-hexen-2-one
  参考文献：
  名称：

  Studies on the structure–enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group

  摘要：

  This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of alpha-diazo-beta-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the alpha-diazo-beta-keto sulfones was varied by the position of a methyl group on the pheny] group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95% yield with 93% ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened P-keto sulfone derivative 15h provides the C-alkylated product as a major product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.046

文献信息

• Studies on the structure–enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation reaction of α-diazo-β-keto sulfones possessing a methyl-substituted phenyl group
  作者：Hiroyuki Takeda、Masahisa Nakada

  DOI：10.1016/j.tetasy.2006.10.046

  日期：2006.11

  This manuscript describes studies on structure-enantioselectivity relationships in the catalytic asymmetric intramolecular cyclopropanation (IMCP) reaction of alpha-diazo-beta-keto sulfones possessing a methyl-substituted phenyl group. Enantioselectivity of the IMCP reaction of the alpha-diazo-beta-keto sulfones was varied by the position of a methyl group on the pheny] group in the substrate, and the 2,3-dimethylphenyl sulfone 11h provided the product 12h in 95% yield with 93% ee. This yield is superior to that of the substrate with a mesityl sulfone 11b, and the product 12h is useful because alkylation of its cyclopropane-opened P-keto sulfone derivative 15h provides the C-alkylated product as a major product. (c) 2006 Elsevier Ltd. All rights reserved.