2-[(3S,5S)-9-methyl-3-oxo-3-phenyl-3lambda6-thia-2-azabicyclo[4.4.0]deca-1(6),2,7,9-tetraen-5-yl]ethanol | 615580-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-[(3S,5S)-9-methyl-3-oxo-3-phenyl-3lambda6-thia-2-azabicyclo[4.4.0]deca-1(6),2,7,9-tetraen-5-yl]ethanol
• 英文别名: 2-[(3S,5S)-9-methyl-3-oxo-3-phenyl-3λ6-thia-2-azabicyclo[4.4.0]deca-1(6),2,7,9-tetraen-5-yl]ethanol
• CAS: 615580-17-1
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: SDKMSVVMGWOUJG-SZNDQCEHSA-N

物化性质

• 沸点：
  495.5±55.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(3S,5S)-9-methyl-3-oxo-3-phenyl-3lambda6-thia-2-azabicyclo[4.4.0]deca-1(6),2,7,9-tetraen-5-yl]ethanol 在 disodium hydrogenphosphate 、 6% sodium amalgam 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以85%的产率得到(3S)-3-(2-amino-4-methylphenyl)butan-1-ol
  参考文献：
  名称：

  Benzothiazines in synthesis. Formal synthesis of erogorgiaene

  摘要：

  A benzothiazine, readily available in enantiomerically pure form via a completely selective, intramolecular addition of a sulfoximine-stabilized carbanion to an alpha, beta-unsaturated ester, could be converted to a precursor to erogorgiaene in good overall yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.184
• 作为产物：
  描述：

  methyl (E)-3-(2-bromo-4-methylphenyl)acrylate 在 palladium diacetate 、 lithium aluminium tetrahydride 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 46.0h， 生成 2-[(3S,5S)-9-methyl-3-oxo-3-phenyl-3lambda6-thia-2-azabicyclo[4.4.0]deca-1(6),2,7,9-tetraen-5-yl]ethanol
  参考文献：
  名称：

  Benzothiazines in synthesis. Formal synthesis of erogorgiaene

  摘要：

  A benzothiazine, readily available in enantiomerically pure form via a completely selective, intramolecular addition of a sulfoximine-stabilized carbanion to an alpha, beta-unsaturated ester, could be converted to a precursor to erogorgiaene in good overall yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.184

文献信息

• Benzothiazines in Synthesis:  Studies Directed toward the Synthesis of Erogorgiaene
  作者：Michael Harmata、Xuechuan Hong、Peter R. Schreiner

  DOI：10.1021/jo701935s

  日期：2008.2.1

  The use of benzothiazenes for the formal total synthesis of erogorgiaene and stereoselective total syntheses of two diastereomers of this natural product is described. In particular, the stereochemical course of a radical cyclization anticipated to give the correct relative stereochemistry for the synthesis of erogorgiaene is discussed utilizing both experimental and computational data.

  描述了将苯并噻氮酮用于五茂铁的正式全合成和该天然产物的两个非对映异构体的立体选择性全合成。特别地，利用实验和计算数据讨论了自由基环化的立体化学过程，该立体化学过程预期将提供正确的相对立体化学，用于合成香气烯。
• Benzothiazines in synthesis. Formal synthesis of erogorgiaene
  作者：Michael Harmata、Xuechuan Hong

  DOI：10.1016/j.tetlet.2005.03.184

  日期：2005.5

  A benzothiazine, readily available in enantiomerically pure form via a completely selective, intramolecular addition of a sulfoximine-stabilized carbanion to an alpha, beta-unsaturated ester, could be converted to a precursor to erogorgiaene in good overall yield. (c) 2005 Elsevier Ltd. All rights reserved.