[bis-((E)-but-2-enyloxy)phosphoryl]diazoacetic acid (3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl ester | 566915-00-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: [bis-((E)-but-2-enyloxy)phosphoryl]diazoacetic acid (3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl ester
• 英文别名: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] 2-[bis[(E)-but-2-enoxy]-oxidophosphaniumyl]-2-diazoacetate
• CAS: 566915-00-2
• 化学式: C₁₆H₂₃N₂O₇P
• 分子量: 386.342
• InChiKey: DOVGREJDEVVLDK-ZAFIRJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  96.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [bis-((E)-but-2-enyloxy)phosphoryl]diazoacetic acid (3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl ester 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,2S,5R,6S)-2-[((E)-But-2-enyl)oxy]-6-methyl-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 、 (1R,2R,5R,6S)-2-[((E)-But-2-enyl)oxy]-6-methyl-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 、 (1S,2S,5S,6R)-2-[((E)-But-2-enyl)oxy]-6-methyl-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 、 (1S,2R,5S,6R)-2-[((E)-But-2-enyl)oxy]-6-methyl-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：

  Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation

  摘要：

  The investigation of substituent effects in the double diastereotopic differentiation of substituted alpha-diazophosphonates using intramolecular cyclopropanation catalyzed by Rh-2(OAc)(4) is reported. Carbene facial selectivity in these transformations is dictated by substrate control in either of two ways: (i) exploitation of (R)-pantolactone as an auxiliary incorporated into the carboester functionality while probing olefinic substituent effects, or (ii) utilization of chiral, non-racemic allylic alcohols incorporated into the phosphonate moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00081-8
• 作为产物：
  描述：

  [bis-((E)-but-2-enyloxy)phosphoryl]acetic acid (3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl ester 在 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到[bis-((E)-but-2-enyloxy)phosphoryl]diazoacetic acid (3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl ester
  参考文献：
  名称：

  Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation

  摘要：

  The investigation of substituent effects in the double diastereotopic differentiation of substituted alpha-diazophosphonates using intramolecular cyclopropanation catalyzed by Rh-2(OAc)(4) is reported. Carbene facial selectivity in these transformations is dictated by substrate control in either of two ways: (i) exploitation of (R)-pantolactone as an auxiliary incorporated into the carboester functionality while probing olefinic substituent effects, or (ii) utilization of chiral, non-racemic allylic alcohols incorporated into the phosphonate moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00081-8