(2S,4R,5R,E)-5-hydroxy-4-((3-methyl-2-pentenoic acid ethyl ester)-5-yl)-2-methyl-1,3-dioxane | 223575-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,4R,5R,E)-5-hydroxy-4-((3-methyl-2-pentenoic acid ethyl ester)-5-yl)-2-methyl-1,3-dioxane
• 英文别名: ethyl (E)-5-[(2S,4R,5R)-5-hydroxy-2-methyl-1,3-dioxan-4-yl]-3-methylpent-2-enoate
• CAS: 223575-81-3
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: BTQCATDZRVFPMY-NWFYNBELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  二硫化碳 、 (2S,4R,5R,E)-5-hydroxy-4-((3-methyl-2-pentenoic acid ethyl ester)-5-yl)-2-methyl-1,3-dioxane 、 碘甲烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 (2S,4R,5R,E)-5-(methylthio)thiocarbonyl-4-((3-methyl-2-pentenoic acid ethyl ester)-5-yl)-2-methyl-1,3-dioxane 、 (1S,2S,3S)-1-methyl-3-phenylmethoxy-2-phenylmethoxymethylcyclopentaveacetic acid ethyl ester 、 (1R,2S,3S)-1-methyl-3-phenylmethoxy-2-phenylmethoxymethylcyclopentaneacetic acid ethyl ester
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380
• 作为产物：
  描述：

  (2S,4S,5R)-5-羟基-2-甲基-1,3-二恶烷-4-甲醛 在 palladium on activated charcoal 盐酸 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (2S,4R,5R,E)-5-hydroxy-4-((3-methyl-2-pentenoic acid ethyl ester)-5-yl)-2-methyl-1,3-dioxane
  参考文献：
  名称：

  Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center

  摘要：

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.

  DOI：

  10.1021/jo9822380

文献信息

• Radical-Mediated Construction of Cyclopentane with Concurrent Formation of a Well-Defined Quaternary Center
  作者：Qiang Zhu、Li-Xin Qiao、Yikang Wu、Yu-Lin Wu

  DOI：10.1021/jo9822380

  日期：1999.4.1

  Synthetic efforts toward the total synthesis of clavulactone dealing with enantioselective construction of the cyclopentane moiety are reported. With a novel radical-mediated cyclization as key step, the current approach allows for concurrent enantioselective construction of a quaternary chiral carbon at the cyclization step. The stereochemistries of the newly formed chiral centers are dictated by the configuration of the C-1 (cf. numbering in 1). The high selectivity observed in this work is ascribed to the conformational advantage of the cyclic acetal, which results in a much better defined transition state than the previously used open-chain counterpart does.