(R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)dihydrofuran-2(3H)-one | 1416253-45-6

• 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-(4-hydroxy-4-methylpentyl)dihydrofuran-2(3H)-one
• 英文别名: (3R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)oxolan-2-one
• CAS: 1416253-45-6
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: IXGFVQDPWDCKBM-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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-(4-hydroxy-4-methylpentyl)dihydrofuran-2(3H)-one 、 (R)-methyl 2,6-dihydroxy-2-(2-hydroxyethyl)-6-methylheptanoate 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 0.33h， 以90%的产率得到(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：

  3-(2-(dibenzylamino)-4-hydroxy-4-methylpentylidene)dihydrofuran-2(3H)-one 在 palladium 10% on activated carbon 、 氢气 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 5.0~60.0 ℃ 、413.7 kPa 条件下， 反应 4.17h， 生成 (R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)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

• A Concise and Scalable Formal Synthesis of the Enantiopure Side-Chain Diester of Homoharringtonine
  作者：Moran Sun、Xin Jia、Yaowen Lai、Hua Yang

  DOI：10.3184/174751915x14189228913336

  日期：2015.1

  The enantiopure side-chain diester of homoharringtonine (HHT) has been prepared in 38% overall yield, from cheap L-aspartic acid by a linear sequence of 10 chemical operations (mean yield per step: 91%). The experimental operation in each step is convenient, economic and prone to scale up. About 7–10 g of the side-chain diester of HHT is easily prepared within one week from 5 g of L-aspartic acid.

  通过 10 步线性化学反应（每一步的平均收率为 91%），以廉价的 L-天冬氨酸为原料，制备出了对映体纯度为 38%的高哈林鸟嘌呤（HHT）侧链二酯。每一步的实验操作都非常方便、经济，而且易于推广。5 克 L-天门冬氨酸可在一周内轻松制备出约 7-10 克 HHT 侧链二酯。
• 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.