(5S,2E)-5-tetrahydropyranyloxy-2-hexenoic acid | 91326-79-3

• 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: (5S,2E)-5-tetrahydropyranyloxy-2-hexenoic acid
• 英文别名: (E,5S)-5-(oxan-2-yloxy)hex-2-enoic acid
• CAS: 91326-79-3
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: FAMXHHANEINPBA-BZQIJHRVSA-N

物化性质

• 沸点：
  376.7±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,2E)-5-tetrahydropyranyloxy-2-hexenoic acid 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 C₆H₃Cl₃COCl 、 camphor-10-sulfonic acid 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 (+)-macrosphelide G
  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：

  ethyl (3S)-3-((tetrahydro-2H-pyran-2-yl)oxy)butanoate 在 lithium hydroxide 、 lithium aluminium tetrahydride 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 30.5h， 生成 (5S,2E)-5-tetrahydropyranyloxy-2-hexenoic acid
  参考文献：
  名称：

  Preparation of O-1∼C-6 and O-7∼C-14 fragments of colletodiol

  摘要：

  DOI：

  10.1016/s0040-4039(01)81187-4

文献信息

• Total synthesis of colletodiol
  作者：Hironori Tsutsui、Oyo Mitsunobu

  DOI：10.1016/s0040-4039(01)81188-6

  日期：——
• 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.
• Preparation of O-1∼C-6 and O-7∼C-14 fragments of colletodiol
  作者：Hironori Tsutsui、Oyo Mitsunobu

  DOI：10.1016/s0040-4039(01)81187-4

  日期：1984.1
• Synthesis of macrosphelides H and G
  作者：Yuichi Kobayashi、Yong-Gang Wang

  DOI：10.1016/s0040-4039(02)00781-5

  日期：2002.6

  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.