(E)-(S)-5-((R)-3-Hydroxy-hex-5-enoyloxy)-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester | 458564-62-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (E)-(S)-5-((R)-3-Hydroxy-hex-5-enoyloxy)-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester
• 英文别名: [(1S)-1-(furan-2-yl)ethyl] (E,5S)-5-[(3R)-3-hydroxyhex-5-enoyl]oxyhex-2-enoate
• CAS: 458564-62-0
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: FRUJMTFDPXJQJO-CWYMFKJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-(S)-5-((R)-3-Hydroxy-hex-5-enoyloxy)-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 呋喃 、 吡啶 、 sodium chlorite 、 2-甲基-2-丁烯 作用下， 以 水 、 丙酮 、 phosphate buffer 、 叔丁醇 为溶剂， 生成 (E)-(S)-5-[(E)-(S)-5-((R)-3-Hydroxy-hex-5-enoyloxy)-hex-2-enoyloxy]-4-oxo-hex-2-enoic acid
  参考文献：
  名称：

  Synthesis of macrosphelides H and G

  摘要：

  A compound with furyl and vinyl groups was designed as an intermediate for synthesis of macrosphelide H. The furyl group was oxidatively transformed into the key C(5)-O(10) part by a two-step conversion of (1) NBS, H2O: (2) NaClO2 without affecting the free hydroxyl group at C(3). thus furnishing the seco acid, while the Wacker oxidation at the final step was used to convert the vinyl group into acetyl group to afford macrosphelide H. This strategy was applied successfully to synthesis or macrosphelide G as well. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00781-5
• 作为产物：
  描述：

  (5S,2E)-5-tetrahydropyranyloxy-2-hexenoic acid 在 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 4-甲基苯磺酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (E)-(S)-5-((R)-3-Hydroxy-hex-5-enoyloxy)-hex-2-enoic acid (S)-1-furan-2-yl-ethyl ester
  参考文献：
  名称：

  Synthesis of macrosphelides H and G

  摘要：

  A compound with furyl and vinyl groups was designed as an intermediate for synthesis of macrosphelide H. The furyl group was oxidatively transformed into the key C(5)-O(10) part by a two-step conversion of (1) NBS, H2O: (2) NaClO2 without affecting the free hydroxyl group at C(3). thus furnishing the seco acid, while the Wacker oxidation at the final step was used to convert the vinyl group into acetyl group to afford macrosphelide H. This strategy was applied successfully to synthesis or macrosphelide G as well. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00781-5