2-((S)-1-Phenyl-ethyl)-isothiazol-3-one | 125458-23-3

• 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: 2-((S)-1-Phenyl-ethyl)-isothiazol-3-one
• 英文别名: 2-[(1S)-1-phenylethyl]-1,2-thiazol-3-one
• CAS: 125458-23-3
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: BDOOJCJSTQZQDM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((S)-1-Phenyl-ethyl)-isothiazol-3-one 在 三氯氧磷 、 氨 作用下， 以 乙腈 为溶剂， 以42%的产率得到N-[(1S)-1-phenylethyl]isothiazol-3-amine
  参考文献：
  名称：

  Enantioselective synthesis, chiroptical properties and absolute configuration of 3-aminosubstituted isothiazole S-oxides

  摘要：

  Herein we report a mild and efficient method to synthesize chiral 3-aminosubstituted isothiazole sulfoxides taking advantage of (+)- and (-)-((8,8-dichlorocamphoryl)sulfonyl)oxaziridine under microwave irradiation. The determination of the absolute configuration of the chiral sulfoxide was achieved by theoretical calculation of the CD spectra. The reason for the observed stereoselectivity, was enlightened by means of analysis of our data using DFT calculations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.023
• 作为产物：
  描述：

  N,N-di-(S)-α-methylbenzyl-3,3-dithiodipropionamide 在 磺酰氯 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 2-((S)-1-Phenyl-ethyl)-isothiazol-3-one
  参考文献：
  名称：

  Enantioselective synthesis, chiroptical properties and absolute configuration of 3-aminosubstituted isothiazole S-oxides

  摘要：

  Herein we report a mild and efficient method to synthesize chiral 3-aminosubstituted isothiazole sulfoxides taking advantage of (+)- and (-)-((8,8-dichlorocamphoryl)sulfonyl)oxaziridine under microwave irradiation. The determination of the absolute configuration of the chiral sulfoxide was achieved by theoretical calculation of the CD spectra. The reason for the observed stereoselectivity, was enlightened by means of analysis of our data using DFT calculations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.023

文献信息

• Synthesis and application of a highly efficient, homochiral dienophile
  作者：Adrian Waldner

  DOI：10.1016/s0040-4039(00)99403-6

  日期：1989.1

  The synthesis and application of a highly efficient, homochiral dienophile is described. Cycloaddition of 2-((S)-1-phenylethyl)-1,2- thiazolin-3-on-(S)-1-oxide with a 1-azadiene and cyclopentadiene affords the corresponding cycloadducts in good yield and excellent diastereoselectivity.

  描述了高效的同手性亲二烯体的合成和应用。2-（（S）-1-苯乙基）-1，2-噻唑啉-3-上-（S）-1-氧化物与1-氮杂二烯和环戊二烯的环加成反应可提供相应的环加合物，收率高，非对映选择性高。
• WALDNER, ADRIAN, TETRAHEDRON LETT., 30,(1989) N3, C. 3061-3064
  作者：WALDNER, ADRIAN

  DOI：——

  日期：——