tert-butyl (4-hydroxy-4-methyl-1-(2-oxodihydrofuran-3-ylidene)pentan-2-yl)carbamate | 1416253-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl (4-hydroxy-4-methyl-1-(2-oxodihydrofuran-3-ylidene)pentan-2-yl)carbamate
• 英文别名: tert-butyl N-[(1E,2S)-4-hydroxy-4-methyl-1-(2-oxooxolan-3-ylidene)pentan-2-yl]carbamate
• CAS: 1416253-40-1
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: XZRUFTNDDZPALT-RJCSOLBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-hydroxy-4-methyl-1-(2-oxodihydrofuran-3-ylidene)pentan-2-yl)carbamate 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 5.0~60.0 ℃ 、413.7 kPa 条件下， 反应 10.5h， 生成 (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)succinic acid
  参考文献：
  名称：

  Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

  摘要：

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.

  DOI：

  10.1021/jo302203g
• 作为产物：
  描述：

  (S)-3-(BOC-氨基)-4-羟基丁酸甲酯 在 magnesium 、 2-碘酰基苯甲酸 作用下， 以 乙醚 、 二甲基亚砜 、 甲苯 为溶剂， 反应 16.0h， 生成 tert-butyl (4-hydroxy-4-methyl-1-(2-oxodihydrofuran-3-ylidene)pentan-2-yl)carbamate
  参考文献：
  名称：

  Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

  摘要：

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.

  DOI：

  10.1021/jo302203g

文献信息

• Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine
  作者：Hua Yang、Moran Sun、Shuguang Zhao、Ming Zhu、Yangla Xie、Changling Niu、Chunlin Li

  DOI：10.1021/jo302203g

  日期：2013.1.18

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.