(3R)-methyl 3-hydroxy-7-(4-methoxybenzyloxy)-2,2-dimethylhept-4-ynoate | 1558003-47-6

• 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: (3R)-methyl 3-hydroxy-7-(4-methoxybenzyloxy)-2,2-dimethylhept-4-ynoate
• 英文别名: methyl (3R)-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2,2-dimethylhept-4-ynoate
• CAS: 1558003-47-6
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: SMAUCAXCMBVMOG-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-methyl 3-hydroxy-7-(4-methoxybenzyloxy)-2,2-dimethylhept-4-ynoate 在 N-碘代丁二酰亚胺 、 三乙基硼 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (3S,4Z)-methyl 3-hydroxy-4-iodo-7-(4-methoxybenzyloxy)-2,2-dimethylhept-4-enoate
  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 N-甲基麻黄碱 、 三氧化硫吡啶 、 zinc trifluoromethanesulfonate 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 64.5h， 生成 (3R)-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

文献信息

• Asymmetric Total Synthesis of (+)-Inthomycin C via O-Directed Free Radical Alkyne Hydrostannation with Ph₃SnH and Catalytic Et₃B: Reinstatement of the Zeeck–Taylor (3<i>R</i>)-Structure for (+)-Inthomycin C
  作者：Karl J. Hale、Milosz Grabski、Soraya Manaviazar、Maciej Maczka

  DOI：10.1021/ol5000499

  日期：2014.2.21

  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.