(E)-5-Methanesulfonyl-6,6-dimethyl-hept-3-en-2-one | 711028-71-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: (E)-5-Methanesulfonyl-6,6-dimethyl-hept-3-en-2-one
• 英文别名: (E)-6,6-dimethyl-5-methylsulfonylhept-3-en-2-one
• CAS: 711028-71-6
• 化学式: C₁₀H₁₈O₃S
• 分子量: 218.317
• InChiKey: SDRYYUYQHCBAGT-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-Methanesulfonyl-6,6-dimethyl-hept-3-en-2-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (E)-(2S,5R)-5-Methanesulfonyl-6,6-dimethyl-hept-3-en-2-ol 、 (E)-(2R,5R)-5-Methanesulfonyl-6,6-dimethyl-hept-3-en-2-ol
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c
• 作为产物：
  描述：

  叔丁基乙酸乙酯 在 lithium aluminium tetrahydride 、 sodium hydride 、 二甲基亚砜 、 二异丙胺 、 间氯过氧苯甲酸 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.67h， 生成 (E)-5-Methanesulfonyl-6,6-dimethyl-hept-3-en-2-one
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c

文献信息

• Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation
  作者：Veejendra K. Yadav、K. Ganesh Babu、Masood Parvez

  DOI：10.1021/jo034608c

  日期：2004.5.1

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.