tetradecyl 2-[(3R)-3-ethenyl-5-oxooxolan-3-yl]acetate | 184873-94-7

• 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: tetradecyl 2-[(3R)-3-ethenyl-5-oxooxolan-3-yl]acetate
• CAS: 184873-94-7
• 化学式: C₂₂H₃₈O₄
• 分子量: 366.541
• InChiKey: SHLJRERNLFKNGN-QFIPXVFZSA-N

物化性质

• 沸点：
  469.2±38.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetradecyl 2-[(3R)-3-ethenyl-5-oxooxolan-3-yl]acetate 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 14.0h， 生成 ((R)-3-Hydroxymethyl-5-oxo-tetrahydro-furan-3-yl)-acetic acid tetradecyl ester
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-l-erythro(threo)-hexono-1,4-lactone and 2-Deoxyapiolactone

  摘要：

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.

  DOI：

  10.1021/jm960525v
• 作为产物：
  描述：

  2-[(3aR,6aR)-2,2-Dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-ethanol 在 chromium(VI) oxide 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 samarium diiodide 、 Celite 、 硫酸 、 四丁基溴化铵 、 三氯化硼 、 sodium hydride 、 溶剂黄146 、 丙酸 、 N,N'-二环己基碳二亚胺 、 silver carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙二醇 、 丙酮 、 苯 为溶剂， 反应 26.83h， 生成 tetradecyl 2-[(3R)-3-ethenyl-5-oxooxolan-3-yl]acetate
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-l-erythro(threo)-hexono-1,4-lactone and 2-Deoxyapiolactone

  摘要：

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.

  DOI：

  10.1021/jm960525v

文献信息

• Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-<scp>l</scp>-<i>erythro(threo)</i>-hexono-1,4-lactone and 2-Deoxyapiolactone
  作者：Jeewoo Lee、Nancy E. Lewin、Peter Acs、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm960525v

  日期：1996.1.1

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.