(1S,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester | 220623-03-0

• 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: (1S,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,3S,4S,7R)-5-oxo-7-phenyl-8-oxa-6-azatricyclo[4.3.0.02,4]nonane-3-carboxylate
• CAS: 220623-03-0
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: ASNBVSUCARSAJR-VXUPGSCNSA-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：

  (1S,1aR,1bS,4R,5aS)-5-Oxo-4-phenyl-hexahydro-3-oxa-4a-aza-cyclopropa[a]pentalene-1-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 ((1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo[4.3.0.0^2,4]non-3-yl)methyl methylsulfonate
  参考文献：
  名称：

  构象约束的赖氨酸类似物的合成

  摘要：

  报道了两种构象受限的赖氨酸类似物的合成。基于3-氮杂-双环[3.1.0]己烷系统的新型类似物1的合成可从已知的三轮车3分八步完成。类似物2的合成是由4-羟基脯氨酸在八个步骤中完成的。两种类似物均经过适当保护以合成Fmoc / Boc固相肽。

  DOI：

  10.1021/jo060210f
• 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 (1S,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

• Synthesis of Conformationally Constrained Lysine Analogues
  作者：Rakesh Ganorkar、Amarnath Natarajan、Ahmed Mamai、José S. Madalengoitia

  DOI：10.1021/jo060210f

  日期：2006.6.1

  The synthesis of two conformationally constrained lysine analogues is reported. The synthesis of the novel analogue 1 based on the 3-aza-bicyclo[3.1.0]hexane system is accomplished from the known tricycle 3 in eight steps. The synthesis of the analogue 2 is accomplished in eight steps from 4-hydroxy proline. Both analogues are synthesized appropriately protected for Fmoc/Boc solid-phase peptide synthesis

  报道了两种构象受限的赖氨酸类似物的合成。基于3-氮杂-双环[3.1.0]己烷系统的新型类似物1的合成可从已知的三轮车3分八步完成。类似物2的合成是由4-羟基脯氨酸在八个步骤中完成的。两种类似物均经过适当保护以合成Fmoc / Boc固相肽。
• 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.