2,2-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hexan-1-ol | 322399-56-4

• 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: 2,2-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hexan-1-ol
• 英文别名: 2,2-Dimethyl-6-(oxan-2-yloxy)hexan-1-ol
• CAS: 322399-56-4
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: GWIIMYSPICZOFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hexan-1-ol 在 lithium hydroxide 、 草酰氯 、 Celite 、 溴 、 sodium hexamethyldisilazane 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (5Z,8Z,11Z,14Z)-20-Bromo-16,16-dimethyl-icosa-5,8,11,14-tetraenoyl chloride
  参考文献：
  名称：

  The Synthesis of N-Vanillyl-arachidonoyl-amide (Arvanil) and its Analogs: An Improved Procedure for the Synthesis of the Key Synthon Methyl 14-Hydroxy-(all-cis)-5,8,11-tetradecatrienoate

  摘要：

  Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to the synthon 6 in a facile five strip sequence (overall yield, 33%). The pharmacological profile of these novel analogs suggests that they may be acting through a novel site of action for anandamide (arachidonylethanolamide, AEA). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00877-2
• 作为产物：
  描述：

  ethyl 2,2-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hexanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以95%的产率得到2,2-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hexan-1-ol
  参考文献：
  名称：

  The Synthesis of N-Vanillyl-arachidonoyl-amide (Arvanil) and its Analogs: An Improved Procedure for the Synthesis of the Key Synthon Methyl 14-Hydroxy-(all-cis)-5,8,11-tetradecatrienoate

  摘要：

  Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to the synthon 6 in a facile five strip sequence (overall yield, 33%). The pharmacological profile of these novel analogs suggests that they may be acting through a novel site of action for anandamide (arachidonylethanolamide, AEA). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00877-2