3-Allyl-2-allyloxy-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,2]oxaphosphepine-3-carboxylic acid tert-butyl ester | 478303-32-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Allyl-2-allyloxy-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,2]oxaphosphepine-3-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 2-oxo-2-prop-2-enoxy-3-prop-2-enyl-4,7-dihydro-1,2lambda5-oxaphosphepine-3-carboxylate；tert-butyl 2-oxo-2-prop-2-enoxy-3-prop-2-enyl-4,7-dihydro-1,2λ5-oxaphosphepine-3-carboxylate
• CAS: 478303-32-1
• 化学式: C₁₆H₂₅O₅P
• 分子量: 328.345
• InChiKey: WKJYCFFSIGGVHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3-Allyl-2-allyloxy-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,2]oxaphosphepine-3-carboxylic acid tert-butyl ester 在 Grubbs catalyst first generation 甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 10a-Oxo-2,5,6,9-tetrahydro-1,10-dioxa-10aλ⁵-phospha-heptalene-5a-carboxylic acid
  参考文献：
  名称：

  Conformationally Constrained α-Boc-Aminophosphonates via Transition Metal-Catalyzed/Curtius Rearrangement Strategies

  摘要：

  A transition metal-catalyzed/Curtius rearrangement sequence toward the development of conformationally constrained alpha-Boc-aminophosphonates 2-6 is described. An approach using the versatile tert-butylphosphonoacetate moieties 1a and 1b to derive an array of mono- and bicyclic alpha-Boc-aminophosphonate systems is presented. Conformational constraint is incorporated using either the ring-closing metathesis reaction catalyzed by the first generation Grubbs catalyst or intramolecular cyclopropanation mediated by Rh-2(OAc)(4). Using the tert-butyl ester functionality in 1a or 1b as a potential amino group, the Curtius rearrangement provides an efficient route toward the target alpha-Boc-aminophosphonates.

  DOI：

  10.1021/jo0262208
• 作为产物：
  描述：

  tert-butyl 2-(bis(allyloxy)phosphoryl)acetate 在 Grubbs catalyst first generation potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-Allyl-2-allyloxy-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,2]oxaphosphepine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Conformationally Constrained α-Boc-Aminophosphonates via Transition Metal-Catalyzed/Curtius Rearrangement Strategies

  摘要：

  A transition metal-catalyzed/Curtius rearrangement sequence toward the development of conformationally constrained alpha-Boc-aminophosphonates 2-6 is described. An approach using the versatile tert-butylphosphonoacetate moieties 1a and 1b to derive an array of mono- and bicyclic alpha-Boc-aminophosphonate systems is presented. Conformational constraint is incorporated using either the ring-closing metathesis reaction catalyzed by the first generation Grubbs catalyst or intramolecular cyclopropanation mediated by Rh-2(OAc)(4). Using the tert-butyl ester functionality in 1a or 1b as a potential amino group, the Curtius rearrangement provides an efficient route toward the target alpha-Boc-aminophosphonates.

  DOI：

  10.1021/jo0262208

文献信息

• Conformationally Constrained α-Boc-Aminophosphonates via Transition Metal-Catalyzed/Curtius Rearrangement Strategies
  作者：Joel D. Moore、Kevin T. Sprott、Paul R. Hanson

  DOI：10.1021/jo0262208

  日期：2002.11.1

  A transition metal-catalyzed/Curtius rearrangement sequence toward the development of conformationally constrained alpha-Boc-aminophosphonates 2-6 is described. An approach using the versatile tert-butylphosphonoacetate moieties 1a and 1b to derive an array of mono- and bicyclic alpha-Boc-aminophosphonate systems is presented. Conformational constraint is incorporated using either the ring-closing metathesis reaction catalyzed by the first generation Grubbs catalyst or intramolecular cyclopropanation mediated by Rh-2(OAc)(4). Using the tert-butyl ester functionality in 1a or 1b as a potential amino group, the Curtius rearrangement provides an efficient route toward the target alpha-Boc-aminophosphonates.