(4-Carbomethoxy-3-buten-2-ylidene)triphenylphosphorane | 53236-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-Carbomethoxy-3-buten-2-ylidene)triphenylphosphorane
• 英文别名: methyl (E)-4-(triphenyl-λ5-phosphanylidene)pent-2-enoate
• CAS: 53236-02-5
• 化学式: C₂₄H₂₃O₂P
• 分子量: 374.419
• InChiKey: WDROTYLXOHJXLE-VHEBQXMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4-Carbomethoxy-3-buten-2-ylidene)triphenylphosphorane 、 正己醛 生成 (Z)-((E)-2-Propenyl)-oct-2-enoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of (−)-Reveromycin B

  摘要：

  The total synthesis of the epidermal growth factor inhibitor reveromycin B (2) is described. A novel, convergent, and stereoselective reaction sequence was utilized to construct the 5,6-spiroketal system 10 which was converted into the natural product 2 by a 16-step sequence.

  DOI：

  10.1021/ol991281m

文献信息

• Synthesis of the lower subunit of rhizoxin
  作者：Dale L. Boger、Timothy T. Curran

  DOI：10.1021/jo00034a010

  日期：1992.4

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.