methyl 3-hydroxy-7-(4-methoxybenzyloxy)-2,2-dimethylhept-4-ynoate | 1558003-69-2

• 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: methyl 3-hydroxy-7-(4-methoxybenzyloxy)-2,2-dimethylhept-4-ynoate
• CAS: 1558003-69-2
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: SMAUCAXCMBVMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 methyl 3-hydroxy-7-(4-methoxybenzyloxy)-2,2-dimethylhept-4-ynoate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以44%的产率得到methyl 7-((4-methoxybenzyl)oxy)-2,2-dimethyl-3-((3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl)oxy)hept-4-ynoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of (+)-Inthomycin C via O-Directed Free Radical Alkyne Hydrostannation with Ph₃SnH and Catalytic Et₃B: Reinstatement of the Zeeck–Taylor (3R)-Structure for (+)-Inthomycin C

  摘要：

  A new pathway to (+)-inthomycin C is reported that exploits an O-directed free radical hydrostannation reaction on (-)-12 and a Stille cross-coupling as key steps. Significantly, the latter process was effected on 19 where a gauche-pentane repulsive interaction could interfere. Our stereochemical studies on the alkynol (-)-12 and the enyne (+)-7 confirm that Ryu and Hatakeyama's (3S)-stereochemical revision of (+)-inthomycin C is invalid and that Zeeck and Taylor's original (3R)-stereostructure for (+)-inthomycin C is correct.

  DOI：

  10.1021/ol5000499
• 作为产物：
  描述：

  羟基三甲基乙酸甲酯 在 正丁基锂 、 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 3-hydroxy-7-(4-methoxybenzyloxy)-2,2-dimethylhept-4-ynoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of (+)-Inthomycin C via O-Directed Free Radical Alkyne Hydrostannation with Ph₃SnH and Catalytic Et₃B: Reinstatement of the Zeeck–Taylor (3R)-Structure for (+)-Inthomycin C

  摘要：

  A new pathway to (+)-inthomycin C is reported that exploits an O-directed free radical hydrostannation reaction on (-)-12 and a Stille cross-coupling as key steps. Significantly, the latter process was effected on 19 where a gauche-pentane repulsive interaction could interfere. Our stereochemical studies on the alkynol (-)-12 and the enyne (+)-7 confirm that Ryu and Hatakeyama's (3S)-stereochemical revision of (+)-inthomycin C is invalid and that Zeeck and Taylor's original (3R)-stereostructure for (+)-inthomycin C is correct.

  DOI：

  10.1021/ol5000499