(Bis-allyloxy-phosphoryl)-diazo-acetic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester | 445218-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (Bis-allyloxy-phosphoryl)-diazo-acetic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
• CAS: 445218-04-2
• 化学式: C₁₄H₁₉N₂O₇P
• 分子量: 358.288
• InChiKey: OGDYJZFSRIVICP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (Bis-allyloxy-phosphoryl)-diazo-acetic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以8%的产率得到(1S,2S,5S)-2-Allyloxy-2-oxo-3-oxa-2λ⁵-phospha-bicyclo[3.1.0]hexane-1-carboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Double Diastereoselective Intramolecular Cyclopropanation to P-Chiral [3.1.0]-Bicyclic Phosphonates

  摘要：

  [GRAPHICS]A double diastereotopic differentiation strategy on a phosphonoacetate template is described. The approach utilizes Rh-2(OAC)(4)-catalyzed intramolecular cyclopropanation (ICP) employing the (R)-pantolactone auxiliary in the ester functionality of the phosphonoacetate. The olefinic diastereofacial selectivity is governed by inherent electronic and steric interactions in the reacting carbene intermediate, while the group selectivity is dictated by the chiral auxiliary. This approach is being developed as an effective method to access bicyclic P-chiral phosphonates.

  DOI：

  10.1021/ol026080o
• 作为产物：
  描述：

  2-(bis(allyloxy)phosphoryl)acetic acid 在 对甲苯磺酰叠氮 、 TEA 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (Bis-allyloxy-phosphoryl)-diazo-acetic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Double Diastereoselective Intramolecular Cyclopropanation to P-Chiral [3.1.0]-Bicyclic Phosphonates

  摘要：

  [GRAPHICS]A double diastereotopic differentiation strategy on a phosphonoacetate template is described. The approach utilizes Rh-2(OAC)(4)-catalyzed intramolecular cyclopropanation (ICP) employing the (R)-pantolactone auxiliary in the ester functionality of the phosphonoacetate. The olefinic diastereofacial selectivity is governed by inherent electronic and steric interactions in the reacting carbene intermediate, while the group selectivity is dictated by the chiral auxiliary. This approach is being developed as an effective method to access bicyclic P-chiral phosphonates.

  DOI：

  10.1021/ol026080o