(4aR,5aS,6R,9aS)-6-methyl-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one | 410075-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (4aR,5aS,6R,9aS)-6-methyl-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one
• 英文别名: (1R,3S,4R,8S,10R)-4-methyl-10-phenyl-2,9,11-trioxa-6-azatricyclo[6.4.0.03,6]dodecan-5-one
• CAS: 410075-06-8
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: CYBUIMPHZOTGRL-AMFXNCCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4aR,5aS,6R,9aS)-6-methyl-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以85%的产率得到(3S,4R,6S,7R)-3-hydroxy-4-(hydroxymethyl)-7-methyl-5-oxacepham
  参考文献：
  名称：

  An entry to 7-amino- and to 2-ethoxycarbonyl-5-dethia-5-oxa-cephams from 1,3-alkylidene-l-erythritol

  摘要：

  The alkoxyallene derived from 1,3-benzylidene-L-erythritol when treated with chlorosulfonyl isocyanate provided diastereomeric beta-lactams with moderate stereoselectivity. After the intramolecular alkylation of the nitrogen atom, these afforded compounds having oxacepham skeletons. The exo-isopropylidene group enabled the introduction of a variety of substituents to the C-7 carbon atom of the cepham, whereas removal of the benzylidene protection followed by the oxidation of 3-OH to the ketone allowed carboxylation of the C-2 carbon atom. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.074
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 1,3-O-benzylidene-2-O-prop-1'-enyl-4-O-mesyl-L-erythrotetritol 生成 (4aR,5aR,6S,9aS)-6-methyl-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one 、 (4aR,5aS,6R,9aS)-6-methyl-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one
  参考文献：
  名称：

  5-Dethia-5-oxacephams：趋向于绝对构型与手性的相关性。

  摘要：

  研究了不同取代的5-dethia-5-oxacephams的手性与它们各自的分子结构之间的关系。发现这些化合物中的β-内酰胺单元的酰胺发色团是非平面的，在氮原子上具有浅金字塔形状。由于非平面性，β-内酰胺系统固有地变得不对称，这由高强度的n-> pi * CD带支持。还发现在研究的草甘膦中内酰胺部分的螺旋度受C（6）碳原子处的绝对构型控制。在此基础上，

  DOI：

  10.1021/jo010657i

文献信息

• An entry to 7-amino- and to 2-ethoxycarbonyl-5-dethia-5-oxa-cephams from 1,3-alkylidene-l-erythritol
  作者：Tong Thanh Danh、Katarzyna Borsuk、Jolanta Solecka、Marek Chmielewski

  DOI：10.1016/j.tet.2006.08.074

  日期：2006.11

  The alkoxyallene derived from 1,3-benzylidene-L-erythritol when treated with chlorosulfonyl isocyanate provided diastereomeric beta-lactams with moderate stereoselectivity. After the intramolecular alkylation of the nitrogen atom, these afforded compounds having oxacepham skeletons. The exo-isopropylidene group enabled the introduction of a variety of substituents to the C-7 carbon atom of the cepham, whereas removal of the benzylidene protection followed by the oxidation of 3-OH to the ketone allowed carboxylation of the C-2 carbon atom. (c) 2006 Elsevier Ltd. All rights reserved.
• 5-Dethia-5-oxacephams:  Toward Correlation of Absolute Configuration and Chiroptical Properties
  作者：Robert Łysek、Katarzyna Borsuk、Marek Chmielewski、Zbigniew Kałuża、Zofia Urbańczyk-Lipkowska、Agata Klimek、Jadwiga Frelek

  DOI：10.1021/jo010657i

  日期：2002.3.1

  The relationship between chiroptical properties of differently substituted 5-dethia-5-oxacephams and their respective molecular structures was investigated. The amide chromophore of the beta-lactam unit in these compounds was found to be nonplanar with a shallow pyramidal configuration at the nitrogen atom. Due to the nonplanarity, the beta-lactam system becomes inherently dissymmetric, which is supported

  研究了不同取代的5-dethia-5-oxacephams的手性与它们各自的分子结构之间的关系。发现这些化合物中的β-内酰胺单元的酰胺发色团是非平面的，在氮原子上具有浅金字塔形状。由于非平面性，β-内酰胺系统固有地变得不对称，这由高强度的n-> pi * CD带支持。还发现在研究的草甘膦中内酰胺部分的螺旋度受C（6）碳原子处的绝对构型控制。在此基础上，