[bis(2-methylallyloxy)phosphoryl]acetic acid tert-butyl ester | 566914-98-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: [bis(2-methylallyloxy)phosphoryl]acetic acid tert-butyl ester
• 英文别名: Tert-butyl 2-[bis(2-methylprop-2-enoxy)phosphoryl]acetate
• CAS: 566914-98-5
• 化学式: C₁₄H₂₅O₅P
• 分子量: 304.323
• InChiKey: RFJUFPIPMDIADA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [bis(2-methylallyloxy)phosphoryl]acetic acid tert-butyl ester 在 对甲苯磺酰叠氮 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到[bis(2-methylallyloxy)phosphoryl]diazoacetic acid tert-butyl 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：

  2-甲基-2-丙烯-1-醇亚磷酸酯(3:1) 、 碘乙酸叔丁酯 反应 90.0h， 以2.4 g的产率得到[bis(2-methylallyloxy)phosphoryl]acetic acid tert-butyl 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

文献信息

• Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation
  作者：Joel D. Moore、Paul R. Hanson

  DOI：10.1016/s0957-4166(03)00081-8

  日期：2003.4

  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.