tert-butyl 4-chloro-2-(2-phenylethyl)-4-(p-tolylsulfinyl)butyrate | 918404-00-9

• 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: tert-butyl 4-chloro-2-(2-phenylethyl)-4-(p-tolylsulfinyl)butyrate
• 英文别名: Tert-butyl 4-chloro-4-(4-methylphenyl)sulfinyl-2-(2-phenylethyl)butanoate；tert-butyl 4-chloro-4-(4-methylphenyl)sulfinyl-2-(2-phenylethyl)butanoate
• CAS: 918404-00-9
• 化学式: C₂₃H₂₉ClO₃S
• 分子量: 421.0
• InChiKey: SXVIXPLKQVNMOA-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  568.0±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-chloro-2-(2-phenylethyl)-4-(p-tolylsulfinyl)butyrate 在 异丙基氯化镁 、 间氯过氧苯甲酸 、 三氟乙酸酐 、 sodium iodide 作用下， 以 四氢呋喃 、 氯仿 、 丙酮 为溶剂， 反应 1.0h， 生成 trans-5-ethoxycarbonyl-3-(2-phenylethyl)dihydrofuran-2-one
  参考文献：
  名称：

  The first example of γ-chloromagnesio γ-lactones: their generation from γ-tolylsulfinyl γ-lactones with isopropylmagnesium chloride, stability, and reaction with electrophiles

  摘要：

  The treatment of gamma-lactones having a sulfinyl group at the gamma-position, which were synthesized from I-chlorovinyl p-tolyl sulfoxides with lithium enolate of carboxylic esters, with isopropyl magnesium chloride in THF at -78 degrees C gave gamma-chloromagnesio gamma-lactones by the sulfoxide-magnesium exchange reaction in high yields. The generated gamma-chloromagnesio gamma-lactones were found to be stable at below -50 degrees C for at least 2 h. The reaction of these gamma-chloromagnesio gamma-lactones with electrophiles and the stereochemistry of the reactions were investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.165
• 作为产物：
  描述：

  2-hydroxyethyl p-tolyl sulfoxide 在 吡啶 、 lithium anion of δ-valerolactam 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl 4-chloro-2-(2-phenylethyl)-4-(p-tolylsulfinyl)butyrate
  参考文献：
  名称：

  The first example of γ-chloromagnesio γ-lactones: their generation from γ-tolylsulfinyl γ-lactones with isopropylmagnesium chloride, stability, and reaction with electrophiles

  摘要：

  The treatment of gamma-lactones having a sulfinyl group at the gamma-position, which were synthesized from I-chlorovinyl p-tolyl sulfoxides with lithium enolate of carboxylic esters, with isopropyl magnesium chloride in THF at -78 degrees C gave gamma-chloromagnesio gamma-lactones by the sulfoxide-magnesium exchange reaction in high yields. The generated gamma-chloromagnesio gamma-lactones were found to be stable at below -50 degrees C for at least 2 h. The reaction of these gamma-chloromagnesio gamma-lactones with electrophiles and the stereochemistry of the reactions were investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.165

文献信息

• γ-Chloromagnesio γ-Lactones and δ-Chloromagnesio δ-Lactones: Generation, Properties, and Synthetic Uses
  作者：Shimpei Sugiyama、Hitomi Shimizu、Shigehiko Fukuda、Tsuyoshi Satoh

  DOI：10.1055/s-0028-1088019

  日期：2009.4

  respectively, by the sulfoxide-magnesium exchange reaction in high yields. Comparing the stability of the γ-chloromagnesio γ-lactones with that of the δ-chloromagnesio δ-lactones, the former was found to be much more stable. The reaction of these γ-chloromagnesio γ-lactones and δ-chloromagnesio δ-lactones with electrophiles and the stereochemistry of the reactions are discussed. γ-chloromagnesio γ-lactone

  在异丙醇中于-78℃下用异丙基氯化镁处理在γ和δ位具有亚磺酰基的γ和δ内酯，分别通过亚砜处理得到γ-氯镁γ-内酯和δ-氯镁δ-内酯。 -镁交换反应的收率很高。通过比较γ-氯镁γ-内酯和δ-氯镁δ-内酯的稳定性，发现前者更加稳定。讨论了这些γ-氯镁γ-内酯和δ-氯镁δ-内酯与亲电试剂的反应以及反应的立体化学。 γ-氯镁γ-内酯-δ-氯镁δ-内酯-亚砜-镁交换反应-有机镁化合物-格氏试剂
• The first example of γ-chloromagnesio γ-lactones: their generation from γ-tolylsulfinyl γ-lactones with isopropylmagnesium chloride, stability, and reaction with electrophiles
  作者：Shimpei Sugiyama、Hitomi Shimizu、Tsuyoshi Satoh

  DOI：10.1016/j.tetlet.2006.09.165

  日期：2006.12

  The treatment of gamma-lactones having a sulfinyl group at the gamma-position, which were synthesized from I-chlorovinyl p-tolyl sulfoxides with lithium enolate of carboxylic esters, with isopropyl magnesium chloride in THF at -78 degrees C gave gamma-chloromagnesio gamma-lactones by the sulfoxide-magnesium exchange reaction in high yields. The generated gamma-chloromagnesio gamma-lactones were found to be stable at below -50 degrees C for at least 2 h. The reaction of these gamma-chloromagnesio gamma-lactones with electrophiles and the stereochemistry of the reactions were investigated. (c) 2006 Elsevier Ltd. All rights reserved.