(1R,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester | 220623-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1R,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester
• 英文别名: methyl (1S,2R,3R,4S,7R)-5-oxo-7-phenyl-8-oxa-6-azatricyclo[4.3.0.02,4]nonane-3-carboxylate
• CAS: 220623-04-1
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: ASNBVSUCARSAJR-YGEZULPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 methylsulfinylcarbanion 、 氨 、 水 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 56.0h， 生成 (1S,2S,5S,6R)-6-(aminomethyl)-3-aza-3-benzylbicyclo<3.1.0>hexyl-2-methanol
  参考文献：
  名称：

  Cyclopropanation Reactions of Pyroglutamic Acid-Derived Synthons with Akylidene Transfer Reagents

  摘要：

  The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.

  DOI：

  10.1021/jo9816109
• 作为产物：
  描述：

  (+)-(3R,7aS)-四氢-3-苯基-3H,5H-吡咯并[1,2-c]噁唑-5-酮 在 双氧水 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， 反应 34.83h， 生成 (1R,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Cyclopropanation Reactions of Pyroglutamic Acid-Derived Synthons with Akylidene Transfer Reagents

  摘要：

  The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.

  DOI：

  10.1021/jo9816109

文献信息

• Cyclopropanation Reactions of Pyroglutamic Acid-Derived Synthons with Akylidene Transfer Reagents
  作者：Rui Zhang、Ahmed Mamai、Jose S. Madalengoitia

  DOI：10.1021/jo9816109

  日期：1999.1.1

  The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.