3-tosyloxy-4-methylpentan-2-one

• 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: 3-tosyloxy-4-methylpentan-2-one
• 英文别名: (2-Methyl-4-oxopentan-3-yl) 4-methylbenzenesulfonate
• 化学式: C₁₃H₁₈O₄S
• 分子量: 270.35
• InChiKey: KNKIGUBCDDTDPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl methyl(tosyloxy)carbamate 在 甲烷磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 3-tosyloxy-4-methylpentan-2-one
  参考文献：
  名称：

  Direct α-Oxytosylation of Carbonyl Compounds:  One-Pot Synthesis of Heterocycles

  摘要：

  N-Methyl-O-tosylhydroxylamine is an effective reagent for the direct alpha-oxytosylation of carbonyl compounds. The reactions proceed smoothly at room temperature in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsymmetrical substrates regioselectivity for primary over secondary centers is observed and complete regiospecificity for primary over tertiary centers is obtained. Addition of a bis-heteronucleophile directly to the crude reaction mixture in a one-pot process leads to the corresponding heterocyclic product.

  DOI：

  10.1021/ol701774y

文献信息

• Rapid synthesis of 3-organosulfonyloxy-2-alkanones under microwave irradiation
  作者：Jong Chan Lee、Sang Hun Oh、In-Goul Song

  DOI：10.1016/s0040-4039(99)01900-0

  日期：1999.12

  Remarkably fast microwave assisted direct regiospecific sulfonyloxylation reactions of 2-alkanones in solvent free condition is described.

  描述了在无溶剂条件下2-链烷酮的非常快速的微波辅助的直接区域特异性磺酰氧基化反应。
• Härtung von säurehärtbaren Zusammensetzungen, enthaltend einen blockierten Härtungskatalysator, unter Verwendung von Wärme
  申请人：CIBA-GEIGY AG

  公开号：EP0132225A2

  公开（公告）日：1985-01-23

  Verbindungen der Formeln (I) oder (II) worin R', R2, R', R4 und n die in Anspruch 1 angegebene Bedeutung haben, sind latente Härtungskatalysatoren, die thermisch aktivierbar sind. Sie finden Verwendung bei der thermischen Härtung von "high-solid"-Industrielacken, Coil-Coating-, Dosen- und Holzlacken.

  式（I）或（II）的化合物 其中 R'、R2、R'、R4 和 n 的含义如权利要求 1 所述。它们可用于高固体份工业涂料、卷材涂料、罐头涂料和木器涂料的热固化。
• Regiospecific synthesis of 3-organosulfonyloxy-2-alkanones
  作者：Jong Chan Lee、Youngsup Choi

  DOI：10.1016/s0040-4039(98)00451-1

  日期：1998.5

  A direct regiospecific preparation method of 3-organosulfonyloxy-2-alkanones from reaction of 2-alkanones with copper(II) organosulfonates is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• US4699949A
  申请人：——

  公开号：US4699949A

  公开（公告）日：1987-10-13
• Direct α-Oxytosylation of Carbonyl Compounds:  One-Pot Synthesis of Heterocycles
  作者：Oliver R. S. John、Niall M. Killeen、Deborah A. Knowles、Sze Chak Yau、Mark C. Bagley、Nicholas C. O. Tomkinson

  DOI：10.1021/ol701774y

  日期：2007.9.1

  N-Methyl-O-tosylhydroxylamine is an effective reagent for the direct alpha-oxytosylation of carbonyl compounds. The reactions proceed smoothly at room temperature in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsymmetrical substrates regioselectivity for primary over secondary centers is observed and complete regiospecificity for primary over tertiary centers is obtained. Addition of a bis-heteronucleophile directly to the crude reaction mixture in a one-pot process leads to the corresponding heterocyclic product.