4-(tetrahydropyran-2-yloxy)-2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15(E)-heptadecatetraenyl>-1,3,3-trimethylpiperidine | 145362-90-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(tetrahydropyran-2-yloxy)-2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15(E)-heptadecatetraenyl>-1,3,3-trimethylpiperidine
• 英文别名: (2S,4S)-1,3,3-trimethyl-4-(oxan-2-yloxy)-2-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl]piperidine
• CAS: 145362-90-9；145416-13-3
• 化学式: C₃₄H₅₉NO₂
• 分子量: 513.848
• InChiKey: QBYWVARJZLQYPM-XQCMIDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(tetrahydropyran-2-yloxy)-2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15(E)-heptadecatetraenyl>-1,3,3-trimethylpiperidine 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以96%的产率得到2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraenyl>-1,3,3-trimethyl-4-piperidinol
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase. 2. Cyclocondensation of .gamma.,.delta.-unsaturated-.beta.-keto esters with imines

  摘要：

  Synthesis and the biological evaluation of ammonium ion analogues of the first carbocyclic cationic intermediate 4 presumed to formed during the cyclization of 2,3-oxidosqualene to protosterol, 2, by 2,3-oxidisqualene-lanosterol cyclase (OSC) is presented. Preparation of the required 4-hydroxy-2,3-substituted-4-piperidine 12 (and its corresponding methiiodide salt 13) involved, as a key step, cyclocondensation of imine 17 with methyl 2-methyl-3-oxo-4-pentenoate (16) to give C-2,C-3-substituted 4-piperidone 15 as a single diastersoisomer. Subsequent elaboration to give 13 was accomplished in six steps in an overall yield of 50%. Analogue 12 inhibited 2,3-oxidosqualene-lanosterol cyclase of Candida albicans with an IC50 of 0.23 muM.

  DOI：

  10.1021/jo00052a043
• 作为产物：
  描述：

  (E)-6-acetoxy-4-methyl-4-hexenal 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 3 A molecular sieve 、 lithium 、 potassium carbonate 、 对甲苯磺酸 、 乙胺 、 N-chlorosuccinimide-dimethylsulfide complex 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 70.5h， 生成 4-(tetrahydropyran-2-yloxy)-2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15(E)-heptadecatetraenyl>-1,3,3-trimethylpiperidine
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase. 2. Cyclocondensation of .gamma.,.delta.-unsaturated-.beta.-keto esters with imines

  摘要：

  Synthesis and the biological evaluation of ammonium ion analogues of the first carbocyclic cationic intermediate 4 presumed to formed during the cyclization of 2,3-oxidosqualene to protosterol, 2, by 2,3-oxidisqualene-lanosterol cyclase (OSC) is presented. Preparation of the required 4-hydroxy-2,3-substituted-4-piperidine 12 (and its corresponding methiiodide salt 13) involved, as a key step, cyclocondensation of imine 17 with methyl 2-methyl-3-oxo-4-pentenoate (16) to give C-2,C-3-substituted 4-piperidone 15 as a single diastersoisomer. Subsequent elaboration to give 13 was accomplished in six steps in an overall yield of 50%. Analogue 12 inhibited 2,3-oxidosqualene-lanosterol cyclase of Candida albicans with an IC50 of 0.23 muM.

  DOI：

  10.1021/jo00052a043

文献信息

• Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase. 2. Cyclocondensation of .gamma.,.delta.-unsaturated-.beta.-keto esters with imines
  作者：Dharmpal S. Dodd、Allan C. Oehlschlager、Nafsika H. Georgopapadakou、Anne Marie Polak、Peter G. Hartman

  DOI：10.1021/jo00052a043

  日期：1992.12

  Synthesis and the biological evaluation of ammonium ion analogues of the first carbocyclic cationic intermediate 4 presumed to formed during the cyclization of 2,3-oxidosqualene to protosterol, 2, by 2,3-oxidisqualene-lanosterol cyclase (OSC) is presented. Preparation of the required 4-hydroxy-2,3-substituted-4-piperidine 12 (and its corresponding methiiodide salt 13) involved, as a key step, cyclocondensation of imine 17 with methyl 2-methyl-3-oxo-4-pentenoate (16) to give C-2,C-3-substituted 4-piperidone 15 as a single diastersoisomer. Subsequent elaboration to give 13 was accomplished in six steps in an overall yield of 50%. Analogue 12 inhibited 2,3-oxidosqualene-lanosterol cyclase of Candida albicans with an IC50 of 0.23 muM.