[(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine | 141781-23-9

• 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: [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine
• CAS: 141781-23-9
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: URLZNDQCFPAHNW-VUVCFOEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine 在 palladium on activated charcoal sodium periodate 、 正丁基锂 、 TEA 、 氢气 、 四氯化钛 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙酸乙酯 为溶剂， -78.0~50.0 ℃ 、101.33 kPa 条件下， 反应 24.5h， 生成 N-(4-Methoxyphenyl)-4-cyclohexyl-3-hydroxybutanamide
  参考文献：
  名称：

  Stereoselective synthesis of azetidin-2-ones, precursors of biologically active syn-3-amino-2-hydroxybutanoic acids

  摘要：

  DOI：

  10.1021/jo00069a048
• 作为产物：
  描述：

  (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 、 甲氧苯胺 生成 [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine
  参考文献：
  名称：

  通过将2-吡啶基硫酯钛烯酸酯添加到手性亚胺中，高度非对映选择性地合成β-内酰胺

  摘要：

  将2-吡啶基硫酯的钛烯醇盐添加到衍生自烷氧基醛的手性亚胺中，可以很好地控制非对映表面，从而轻松获得重要的碳青霉烯类抗生素。

  DOI：

  10.1016/s0040-4039(00)91874-4

文献信息

• Synthesis of β-lactams by condensation of the tin enolates of 2-pyridylthioesters with imines. A comparison between titanium and tin enolates
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4020(01)85649-0

  日期：1994.1

  SnBr4 affords the corresponding tin(IV) enolates that add to imines to give β-lactams in fair to good yields and with various degree of trans/cis stereoselectivity. Examples of highly diastereofacially selective reactions carried out on a chiral thioester and on a chiral imine are also reported. The results are compared with those obtained in the condensations promoted by TiCl4 and TiBr4.

  将三乙胺加到2-吡啶基硫代酯和SnCl 4或SnBr 4的混合物中，得到相应的锡（IV）烯醇盐，它们加到亚胺上，以公平至良好的收率和不同程度的反式/顺式立体选择性得到β-内酰胺。还报道了在手性硫酯和手性亚胺上进行的高度非对映选择性反应的实例。将结果与由TiCl 4和TiBr 4促进的缩合中获得的结果进行比较。
• Stereoselective synthesis of .beta.-lactams by condensation of titanium enolates of 2-pyridyl thioesters with imines
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Pier Giorgio Cozzi

  DOI：10.1021/jo00041a019

  日期：1992.7

  A mild and versatile one-pot synthesis of beta-lactams has been performed by condensation of the easily generated titantium enolates of 2-pyridyl thioesters with imines employing chiral reaction partners. Both imines obtained from enantiomerically pure alkoxy aldehydes and the enolate derived from 3-hydroxybutyrate showed high diastereofacial preferences, efficiently transferring the stereochemical information to the stereocenters of the azetidinone ring. Advanced precursors of (+)-PS-5, (+)-PS-6, thienamycin, and 1-beta-methylthienamycin were prepared to illustrate the potential of this method. A H-1-NMR study of the enolization process and a tentative rationalization of the stereochemical results are presented.
• Yb(OTf)₃-Catalyzed One-Pot Synthesis of β-Lactams from Silyl Ketene Thioacetals by a Two- or a Three-Component Reaction
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Valentina Molteni、Olaf Schupp

  DOI：10.1021/jo960844u

  日期：1996.11.15