2-(甲基磺酰基)-1-(2-吡啶基)-乙酮 | 27302-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(甲基磺酰基)-1-(2-吡啶基)-乙酮
• 英文名称: 2-methanesulfonyl-1-pyridin-2-yl-ethanone
• 英文别名: 2-Methylsulfonyl-1-(pyridin-2-yl)ethanone；2-methylsulfonyl-1-pyridin-2-ylethanone
• CAS: 27302-93-8
• 化学式: C₈H₉NO₃S
• mdl: MFCD01941305
• 分子量: 199.23
• InChiKey: ZGMMUHVILAEGAA-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107
• 沸点：
  82°C/8mm
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-(甲基磺酰基)-1-(2-吡啶基)-乙酮 在 sodium hydroxide 、 sodium tetrahydroborate 、 四丁基碘化铵 作用下， 以 乙醇 为溶剂， 生成 2-(1-methoxy-2-(methylsulphonyl)ethyl)pyridine
  参考文献：
  名称：

  Synthesis and conformational analysis of some oxisuran metabolites and their o-methylderivatives

  摘要：

  DOI：

  10.1016/s0040-4020(01)90316-3
• 作为产物：
  描述：

  2-溴-1-(2-吡啶基)-1-乙酮氢溴酸 在 sodium periodate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 生成 2-(甲基磺酰基)-1-(2-吡啶基)-乙酮
  参考文献：
  名称：

  Synthesis and conformational analysis of some oxisuran metabolites and their o-methylderivatives

  摘要：

  DOI：

  10.1016/s0040-4020(01)90316-3

文献信息

• Reactivities of isomeric (1-dimethylaminovinyl)pyridines. Reaction with sulfene
  作者：L. N. Koikov、P. B. Terent'ev、I. P. Gloriozov、V. N. Torocheshnikov、V. N. Baidin、Yu. G. Bundel

  DOI：10.1007/bf00514462

  日期：1983.5
• Michael Reactions of β-Keto Sulfoxides and β-Keto Sulfones
  作者：José L. Marco

  DOI：10.1021/jo9705982

  日期：1997.9.1

  The unprecedented Michael additions of racemic or enantiomerically pure beta-keto sulfoxides (1, 6, 10-12) and beta-keto sulfones (23, 25, 27, 29, 30) to the highly stabilized Michael accepters 2, 4, 8, and 21, 31, and 32 are described. The process proceeds efficiently, under very mild reaction conditions: ethanol, piperidine (catalytic), room temperature. The reaction of the beta-keto sulfoxides having the 2-pyridyl ketone moiety, with arylidenemalononitriles (2, 4) and alpha-cyanocinnamates (8) has given the polyfunctionalized 2-amino-4H-pyran adducts (3, 5, 7, 9), in high yield, with total diastereo-and enantioselectivity. The reaction of 2-pyridyl ketone containing beta-keto sulfone 23 with arylidenemalononitrile (2) gave the polyfunctionalized 2-amino-4H-pyran 24, in high yield. Similar beta-keto sulfoxides (10-12) or beta-keto sulfones (25, 27), lacking the 2-pyridyl ketone moiety, underwent the same reaction, but with lower yields and poor diastereoselection. In some cases, noncyclized intermediates have been detected. The beta-keto sulfones 29 and 30 did not react under the same experimental conditions. Simple Michael accepters such as ethyl acrylate, cinnamonitrile, or methyl vinyl ketone proved also to be reluctant to react with beta-keto sulfoxides 1. In summary, the powerful, strong, and particularly efficient stereodirecting properties of the 2-pyridyl ketone moiety embodied in the beta-keto sulfoxides 1 and 6 or beta-keto sulfone 23 have been observed for the first time. This fact coupled to the apparently critical and necessary influence of the pi-pi stacking interaction in the approach of reactants is discussed in depth here and used with obvious advantages in important synthetic transformations.
• Michael Additions of .alpha.-Sulfinyl and .alpha.-Sulfonyl Carbanions: The Unprecedented Reaction of .beta.-Keto Sulfoxides and .beta.-Keto Sulfones with Highly Stabilized Michael Acceptors
  作者：Jose-Luis Marco、Inmaculada Fernandez、Noureddine Khiar、Paloma Fernandez、Antonio Romero

  DOI：10.1021/jo00126a014

  日期：1995.10
• KOJKOV, L. N.;TERENTEV, P. B.;GLORIOZOV, I. P.;TOROCHESHNIKOV, V. N.;BAJD+, XIMIYA GETEROTSIKL. SOEDIN., 1983, N 5, 643-650
  作者：KOJKOV, L. N.、TERENTEV, P. B.、GLORIOZOV, I. P.、TOROCHESHNIKOV, V. N.、BAJD+

  DOI：——

  日期：——
• GARCIA, RUANO J. L.;PEDREGAL, C.;RODRIGUEZ, J. H., TETRAHEDRON, 43,(1987) N 19, 4407-4416
  作者：GARCIA, RUANO J. L.、PEDREGAL, C.、RODRIGUEZ, J. H.

  DOI：——

  日期：——