(E)-(S)-5-Hydroxy-hex-2-enoic acid (S)-1-methyl-2-((E)-(S)-1-methyl-2,5-dioxo-pent-3-enyloxycarbonyl)-ethyl ester | 344362-55-6

• 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: (E)-(S)-5-Hydroxy-hex-2-enoic acid (S)-1-methyl-2-((E)-(S)-1-methyl-2,5-dioxo-pent-3-enyloxycarbonyl)-ethyl ester
• 英文别名: [(2S)-4-[(E,2S)-3,6-dioxohex-4-en-2-yl]oxy-4-oxobutan-2-yl] (E,5S)-5-hydroxyhex-2-enoate
• CAS: 344362-55-6
• 化学式: C₁₆H₂₂O₇
• 分子量: 326.346
• InChiKey: KVUXZEDXKHIYCE-VYQMIDNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-(S)-5-Hydroxy-hex-2-enoic acid (S)-1-methyl-2-((E)-(S)-1-methyl-2,5-dioxo-pent-3-enyloxycarbonyl)-ethyl ester 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium tetrahydroborate 、 2-甲基-2-丁烯 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 acetate buffer 、 甲苯 、 叔丁醇 为溶剂， 反应 6.0h， 生成 [(2S,6S,7R,8E,12S,14E)-2,6,12-trimethyl-4,10,16-trioxo-1,5,11-trioxacyclohexadeca-8,14-dien-7-yl] 3,5-dinitrobenzoate
  参考文献：
  名称：

  First total synthesis of macrosphelides C and F

  摘要：

  Macrosphelides C and F were synthesized by lactonization of 14-oxo seco acids at the O(10)-C(11) bond followed by reduction and Mitsunobu inversion of the resulting hydroxyl group. The seco acids were prepared from the corresponding furans by furan ring-opening with NBS followed by further oxidation of the 4-oxo-2-alkenals with NaClO2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00285-4
• 作为产物：
  描述：

  (5S,2E)-5-tetrahydropyranyloxy-2-hexenoic acid 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 camphor-10-sulfonic acid 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 28.0h， 生成 (E)-(S)-5-Hydroxy-hex-2-enoic acid (S)-1-methyl-2-((E)-(S)-1-methyl-2,5-dioxo-pent-3-enyloxycarbonyl)-ethyl ester
  参考文献：
  名称：

  First total synthesis of macrosphelides C and F

  摘要：

  Macrosphelides C and F were synthesized by lactonization of 14-oxo seco acids at the O(10)-C(11) bond followed by reduction and Mitsunobu inversion of the resulting hydroxyl group. The seco acids were prepared from the corresponding furans by furan ring-opening with NBS followed by further oxidation of the 4-oxo-2-alkenals with NaClO2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00285-4

文献信息

• First total synthesis of macrosphelides C and F
  作者：Yuichi Kobayashi、Hukum P Acharya

  DOI：10.1016/s0040-4039(01)00285-4

  日期：2001.4

  Macrosphelides C and F were synthesized by lactonization of 14-oxo seco acids at the O(10)-C(11) bond followed by reduction and Mitsunobu inversion of the resulting hydroxyl group. The seco acids were prepared from the corresponding furans by furan ring-opening with NBS followed by further oxidation of the 4-oxo-2-alkenals with NaClO2. (C) 2001 Elsevier Science Ltd. All rights reserved.