(R)-3-hydroxy-3-(3-hydroxy-3-methylbutyl)dihydrofuran-2(3H)-one | 1416253-59-2

• 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: (R)-3-hydroxy-3-(3-hydroxy-3-methylbutyl)dihydrofuran-2(3H)-one
• 英文别名: (3R)-3-hydroxy-3-(3-hydroxy-3-methylbutyl)oxolan-2-one
• CAS: 1416253-59-2
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: JBNTXPUSTTVQFF-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-3-(3-hydroxy-3-methylbutyl)dihydrofuran-2(3H)-one 在 sodium hydroxide 、 盐酸 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium formate 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 5.33h， 以90%的产率得到(R)-2-(3-hydroxy-6,6-dimethyl-2-oxotetrahydro-2H-pyran-3-yl)acetic 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：

  tert-butyl ((2R,3R,E)-3-((tert-butyldimethylsilyl)oxy)-1-(2-oxodihydrofuran-3(2H)-ylidene)butan-2-yl)carbamate 在 盐酸 、 manganese(IV) oxide 、 palladium 10% on activated carbon 、 氢气 、 间氯过氧苯甲酸 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， -78.0~60.0 ℃ 、413.7 kPa 条件下， 反应 18.33h， 生成 (R)-3-hydroxy-3-(3-hydroxy-3-methylbutyl)dihydrofuran-2(3H)-one
  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.