dimethyl (3S,5R)-3,5-dimethyl-2-oxo-6-[(triethylsilyl)oxy]hexylphosphonate | 869210-93-5

• 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: dimethyl (3S,5R)-3,5-dimethyl-2-oxo-6-[(triethylsilyl)oxy]hexylphosphonate
• 英文别名: (3S,5R)-1-dimethoxyphosphoryl-3,5-dimethyl-6-triethylsilyloxyhexan-2-one
• CAS: 869210-93-5
• 化学式: C₁₆H₃₅O₅PSi
• 分子量: 366.51
• InChiKey: NBKJFVUWAVNBKJ-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  dimethyl (3S,5R)-3,5-dimethyl-2-oxo-6-[(triethylsilyl)oxy]hexylphosphonate 、 2,4-hexadienal 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R,4S)-2,4-dimethyl-1-triethylsilyloxy-(6E,8E,10Z)-6,8,10-dodecatrien-5-one 、 (2R,4S)-2,4-dimethyl-1-triethylsilyloxy-(6E,8E,10E)-6,8,10-dodecatrien-5-one
  参考文献：
  名称：

  Synthesis of the Carbocyclic Skeleton of Abyssomicins C and D

  摘要：

  [GRAPHICS]Intramolecular Diels-Alder substrate trienyl methylenebutenolide 5 was prepared in six steps by coupling 3-methoxy-4-methylenebutenolide (6) with trienone keto aldehyde 7. Heating 5 in CHCl3 for 2 d at 70 degrees C afforded 80% of a single Diels-Alder adduct 4 with the complete carbon skeleton of abyssomicin C. Addition of thiophenoxide to the enone double bond of 4 followed by an intramolecular Michael addition afforded 15 with the abyssomicin D carbon skeleton.

  DOI：

  10.1021/ol0518941
• 作为产物：
  描述：

  (+)-(2S,4R)-cis-2,4-dimethyl-δ-valerolactone 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.0h， 生成 dimethyl (3S,5R)-3,5-dimethyl-2-oxo-6-[(triethylsilyl)oxy]hexylphosphonate
  参考文献：
  名称：

  Synthesis of the Carbocyclic Skeleton of Abyssomicins C and D

  摘要：

  [GRAPHICS]Intramolecular Diels-Alder substrate trienyl methylenebutenolide 5 was prepared in six steps by coupling 3-methoxy-4-methylenebutenolide (6) with trienone keto aldehyde 7. Heating 5 in CHCl3 for 2 d at 70 degrees C afforded 80% of a single Diels-Alder adduct 4 with the complete carbon skeleton of abyssomicin C. Addition of thiophenoxide to the enone double bond of 4 followed by an intramolecular Michael addition afforded 15 with the abyssomicin D carbon skeleton.

  DOI：

  10.1021/ol0518941

文献信息

• Synthesis of the Carbocyclic Skeleton of Abyssomicins C and D
  作者：Barry B. Snider、Yefen Zou

  DOI：10.1021/ol0518941

  日期：2005.10.1

  [GRAPHICS]Intramolecular Diels-Alder substrate trienyl methylenebutenolide 5 was prepared in six steps by coupling 3-methoxy-4-methylenebutenolide (6) with trienone keto aldehyde 7. Heating 5 in CHCl3 for 2 d at 70 degrees C afforded 80% of a single Diels-Alder adduct 4 with the complete carbon skeleton of abyssomicin C. Addition of thiophenoxide to the enone double bond of 4 followed by an intramolecular Michael addition afforded 15 with the abyssomicin D carbon skeleton.