1,2-bis(4-methoxyphenyl)spiro[azetidine-3,9'-xanthen]-4-one | 1150619-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,2-bis(4-methoxyphenyl)spiro[azetidine-3,9'-xanthen]-4-one
• 英文别名: 1,4-Bis(4-methoxyphenyl)spiro[azetidine-3,9'-xanthene]-2-one；1,4-bis(4-methoxyphenyl)spiro[azetidine-3,9'-xanthene]-2-one
• CAS: 1150619-71-8
• 化学式: C₂₉H₂₃NO₄
• 分子量: 449.506
• InChiKey: MPSJQNBTNMVHHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  呫吨-9-甲酸 、 N-(4-甲氧基亚苄基)-4-甲氧基苯胺 在 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到1,2-bis(4-methoxyphenyl)spiro[azetidine-3,9'-xanthen]-4-one
  参考文献：
  名称：

  An Easy and Convenient Synthesis of β-Lactams via a One-Pot Staudinger Reaction with 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride Starting from Substituted Carboxylic Acids

  摘要：

  报道了一种简单便捷的2-氮杂环丁酮的直接合成方法。通过4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯盐（DMTMM）催化亚胺和羧酸的[2+2]环加成反应，实现了一系列2-氮杂环丁酮的高产率合成。产物易于分离，因为副产物在水中具有很高的溶解性。

  DOI：

  10.2174/1570178611666141201224959

文献信息

• A facile and effective synthesis of 2-azetidinones via phosphonitrilic chloride
  作者：Maaroof Zarei

  DOI：10.1016/j.tet.2013.05.121

  日期：2013.8

  The Staudinger reaction of imines to β-lactams was successfully achieved with substituted acetic acid and phosphonitrilic chloride in one-pot under mild conditions. Several types of β-lactams, especially 3-electron-withdrawing group β-lactams, can be synthesized by this versatile and efficient method in good to excellent yields. This method is simple, clean, and the by-products were removed by simple

  在温和的条件下，在一锅中成功地用取代的乙酸和磷腈氯化物成功实现了亚胺对β-内酰胺的施陶丁格反应。通过这种通用且有效的方法，可以以良好或优异的产率合成几种类型的β-内酰胺，尤其是3个吸电子基团β-内酰胺。该方法简单，清洁，并且通过简单的水后处理除去了副产物。考虑了溶剂，试剂的摩尔比和温度的影响。
• An Easy and Convenient Synthesis of β-Lactams via a One-Pot Staudinger Reaction with 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride Starting from Substituted Carboxylic Acids
  作者：Maaroof Zarei

  DOI：10.2174/1570178611666141201224959

  日期：2015.1.1

  An easy and convenient direct synthesis of 2-azetidinones is described. The [2+2] cycloaddition reaction of imines and carboxylic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) has been employed to synthesize a variety of 2-azetidinones in high yields. The products were easily isolated because the byproducts are highly soluble in water.

  报道了一种简单便捷的2-氮杂环丁酮的直接合成方法。通过4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯盐（DMTMM）催化亚胺和羧酸的[2+2]环加成反应，实现了一系列2-氮杂环丁酮的高产率合成。产物易于分离，因为副产物在水中具有很高的溶解性。
• The Vilsmeier reagent: a useful and versatile reagent for the synthesis of 2-azetidinones
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tet.2009.02.005

  日期：2009.4

  and oxalyl chloride or thionyl chloride, works as a versatile acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acid and imines in one-pot synthesis under mild conditions. Monocyclic, spirocyclic and 3-electron-withdrawing group β-lactams were synthesized by this method and optimization of conditions were performed.

  （氯亚甲基）二甲基氯化铵（Vilsmeier试剂），可以轻松地由N，N-二甲基甲酰胺和草酰氯或亚硫酰氯制备，可作为通用的酸活化剂，用于直接[2 + 2]烯酮-亚胺环加成取代的乙酸和亚胺在温和条件下一锅合成。用该方法合成了单环，螺环和3个吸电子基β-内酰胺，并进行了条件优化。
• Utilization of DMF–PhCOCl Adduct as an Acid Activator in a New and Convenient Method for Preparation of β-Lactams
  作者：Maaroof Zarei

  DOI：10.1246/bcsj.20110323

  日期：2012.3.15

  An efficient one-pot synthesis of β-lactams by the reaction of imines with acetic acid derivatives in the presence of DMF and benzoyl chloride adduct, a cheap reagent, has been described. Optimizat...

  已经描述了通过亚胺与乙酸衍生物在 DMF 和苯甲酰氯加合物（一种廉价试剂）存在下的反应，高效地一锅法合成 β-内酰胺。优化...
• A straightforward approach to 2-azetidinones from imines and carboxylic acids using dimethyl sulfoxide and acetic anhydride
  作者：Maaroof Zarei

  DOI：10.1016/j.tetlet.2014.07.089

  日期：2014.9

  The direct synthesis of 2-azetidinones from imines and carboxylic acids under mild conditions is developed. Dimethyl sulfoxide (DMSO) can be activated by acetic anhydride and the resulting active species is used for the in situ generation of ketenes from carboxylic acids. This method is cheap, simple, convenient, and efficient and the products are easily isolated.

  开发了在温和条件下由亚胺和羧酸直接合成2-氮杂环丁酮的方法。二甲基亚砜（DMSO）可以被乙酸酐活化，所得的活性物质可用于从羧酸原位生成乙烯酮。该方法便宜，简单，方便，高效，并且产品易于分离。