[5-Hydroxymethyl-2,2-dioxo-3-tetradec-(E)-ylidene-2λ⁶-[1,2]oxathiolan-5-yl]-methanol | 213122-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 英文名称: [5-Hydroxymethyl-2,2-dioxo-3-tetradec-(E)-ylidene-2λ⁶-[1,2]oxathiolan-5-yl]-methanol
• CAS: 213122-52-2
• 化学式: C₁₉H₃₆O₅S
• 分子量: 376.558
• InChiKey: WPRXHNLKOGJYOC-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  25.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [5-Hydroxymethyl-2,2-dioxo-3-tetradec-(E)-ylidene-2λ⁶-[1,2]oxathiolan-5-yl]-methanol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以53%的产率得到Acetic acid 5-hydroxymethyl-2,2-dioxo-3-tetradec-(E)-ylidene-2λ⁶-[1,2]oxathiolan-5-ylmethyl ester
  参考文献：
  名称：

  Conformationally constrained analogues of diacylglycerol (DAG). 14.1 Dissection of the roles of the sn-1 and sn-2 carbonyls in DAG mimetics by isopharma cophore replacement

  摘要：

  The replacement of the sn-l and sn-2 carbonyl esters in DAG-surrogate lactones by sulfonate esters showed that their isosteric properties in protein kinase C binding are controlled by the location of the hydrophobic alkyl chain on the molecule. The CO and SO2 groups appear to be true isosteres only when they are adjacent to the alkyl chain, which is presumed to insert normal to the lipid bilayer. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(98)00307-2
• 作为产物：
  描述：

  肉豆蔻醛 在 sodium tetrahydroborate 、 sodium periodate 、 正丁基锂 、 硫酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 生成 [5-Hydroxymethyl-2,2-dioxo-3-tetradec-(E)-ylidene-2λ⁶-[1,2]oxathiolan-5-yl]-methanol
  参考文献：
  名称：

  Conformationally constrained analogues of diacylglycerol (DAG). 14.1 Dissection of the roles of the sn-1 and sn-2 carbonyls in DAG mimetics by isopharma cophore replacement

  摘要：

  The replacement of the sn-l and sn-2 carbonyl esters in DAG-surrogate lactones by sulfonate esters showed that their isosteric properties in protein kinase C binding are controlled by the location of the hydrophobic alkyl chain on the molecule. The CO and SO2 groups appear to be true isosteres only when they are adjacent to the alkyl chain, which is presumed to insert normal to the lipid bilayer. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(98)00307-2