3,3-dimethyl-2-methylsulfanyl-butyraldehyde | 69769-61-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,3-dimethyl-2-methylsulfanyl-butyraldehyde
• 英文别名: 3,3-Dimethyl-2-methylsulfanylbutanal
• CAS: 69769-61-5
• 化学式: C₇H₁₄OS
• 分子量: 146.254
• InChiKey: FEGLWIKCCQIULN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-2-methylsulfanyl-butyraldehyde 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 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
• 作为产物：
  描述：

  叔丁基乙酸乙酯 在 lithium aluminium tetrahydride 、 二甲基亚砜 、 二异丙胺 、 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 6.17h， 生成 3,3-dimethyl-2-methylsulfanyl-butyraldehyde
  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

• Reaction of ozone with vinyl sulphides. Reactions retaining hydrocarbon chains
  作者：Raymond Chaussin、Pierre Leriverend、Daniel Paquer

  DOI：10.1039/c39780001032

  日期：——

  Ozone reacts with vinyl sulphides and gives, with thiopinacolone and thiocamphor derivatives, products containing unmodified hydrocarbon chains; however, with 4-alkylthio-2,6-dimethylhept-3-ene the classical reaction of cleavage of the double bond has been observed.

  臭氧与乙烯基硫化物反应，并与噻菌灵酮和硫代樟脑衍生物生成含有未修饰烃链的产物；然而，对于4-烷硫基-2，6-二甲基庚-3-烯，已经观察到双键断裂的经典反应。
• CHAUSSIN R.; LERIVEREND P.; PAQUER D., J. CHEM. SOC. CHEM. COMMUN., 1978, NO 23, 1032-1033
  作者：CHAUSSIN R.、 LERIVEREND P.、 PAQUER D.

  DOI：——

  日期：——
• 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.