(4S,6R,7S,9E)-6-hydroxy-7-methyl-4-prop-2-enyl-16-tri(propan-2-yl)silyloxy-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-2-one | 507480-18-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (4S,6R,7S,9E)-6-hydroxy-7-methyl-4-prop-2-enyl-16-tri(propan-2-yl)silyloxy-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-2-one
• CAS: 507480-18-4
• 化学式: C₂₈H₄₄O₄Si
• 分子量: 472.74
• InChiKey: JRLHFTVPKFHZIS-SFDNUGTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,6R,7S,9E)-6-hydroxy-7-methyl-4-prop-2-enyl-16-tri(propan-2-yl)silyloxy-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-2-one 在 四丁基氟化铵 、 silver nitrate 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (4S,6R,7S,9E)-6-[tert-butyl(diphenyl)silyl]oxy-16-hydroxy-4-(3-hydroxypropyl)-7-methyl-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-2-one
  参考文献：
  名称：

  Formal Total Synthesis of Salicylihalamides A and B

  摘要：

  An efficient synthesis of the macrolactone 3 of the salicylihalamides in 10 linear steps from alkene 6 is described. The key steps involved a Stille coupling between the chiral stannane 5 and benzyl bromide 4, which produced alkene 15 in good yield, and subsequent base-induced macrolactonization then gave compound 3. Macrolactone 3 was then converted into the known salicylihalamide A intermediate 18 in a three-step sequence. Compound 3 was also converted into another known salicylihalamide A and B intermediate 23 in a five-step sequence.

  DOI：

  10.1021/jo026798h
• 作为产物：
  描述：

  2-羟基-6-甲基苯甲酸 在 tris-(dibenzylideneacetone)dipalladium(0) 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 三(2-呋喃基)膦 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 四氯化碳 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 39.5h， 生成 (4S,6R,7S,9E)-6-hydroxy-7-methyl-4-prop-2-enyl-16-tri(propan-2-yl)silyloxy-3-oxabicyclo[10.4.0]hexadeca-1(12),9,13,15-tetraen-2-one
  参考文献：
  名称：

  Formal Total Synthesis of Salicylihalamides A and B

  摘要：

  An efficient synthesis of the macrolactone 3 of the salicylihalamides in 10 linear steps from alkene 6 is described. The key steps involved a Stille coupling between the chiral stannane 5 and benzyl bromide 4, which produced alkene 15 in good yield, and subsequent base-induced macrolactonization then gave compound 3. Macrolactone 3 was then converted into the known salicylihalamide A intermediate 18 in a three-step sequence. Compound 3 was also converted into another known salicylihalamide A and B intermediate 23 in a five-step sequence.

  DOI：

  10.1021/jo026798h

文献信息

• Formal Total Synthesis of Salicylihalamides A and B
  作者：Georgina A. Holloway、Helmut M. Hügel、Mark A. Rizzacasa

  DOI：10.1021/jo026798h

  日期：2003.3.1

  An efficient synthesis of the macrolactone 3 of the salicylihalamides in 10 linear steps from alkene 6 is described. The key steps involved a Stille coupling between the chiral stannane 5 and benzyl bromide 4, which produced alkene 15 in good yield, and subsequent base-induced macrolactonization then gave compound 3. Macrolactone 3 was then converted into the known salicylihalamide A intermediate 18 in a three-step sequence. Compound 3 was also converted into another known salicylihalamide A and B intermediate 23 in a five-step sequence.