2-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenyl)-3-O-(4-methoxyphenyl)-sn-glycerol | 1027646-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenyl)-3-O-(4-methoxyphenyl)-sn-glycerol
• 英文别名: [4-[(Z)-13-[(2R)-1-hydroxy-3-(4-methoxyphenoxy)propan-2-yl]oxytridec-4-enyl]phenyl]-phenylmethanone
• CAS: 1027646-81-6
• 化学式: C₃₆H₄₆O₅
• 分子量: 558.758
• InChiKey: FSUPDYZKLJHRTM-KZJYKYPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  41
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenyl)-3-O-(4-methoxyphenyl)-sn-glycerol 在 ammonium cerium(IV) nitrate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 1-O-methoxymethyl-2-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of Photoactivatable Analogues of Lysophosphatidic Acid and Covalent Labeling of Plasma Proteins

  摘要：

  Lysophosphatidic acids bearing a benzophenone group in either the sn-1 or sn-2 chain of an oleoyl-type ester or oleyl-type ether chain and P-32 in the phosphate group were synthesized. The benzophenone moiety was introduced by selective hydroboration of the double bond of enyne 11 at low temperature, followed by a Suzuki reaction with 4-bromobenzophenone. The key intermediates for the preparation of ester-linked lysophosphatidic acid (LPA) I and 3 were obtained in one pot by a modified DIBAL-H reduction of orthoformate intermediate 22. These probes were shown to covalently modify a single protein target in rat plasma containing albumin and several protein targets in rat plasma containing a low level of albumin.

  DOI：

  10.1021/jo052030w
• 作为产物：
  描述：

  (S)-2,2-Dibutyl-4-(4-methoxy-phenoxymethyl)-[1,3,2]dioxastannolane 、 4-((Z)-bromotridec-4-enyl)benzophenone 在 18-冠醚-6 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到1-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenyl)-3-O-(4-methoxyphenyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of Photoactivatable Analogues of Lysophosphatidic Acid and Covalent Labeling of Plasma Proteins

  摘要：

  Lysophosphatidic acids bearing a benzophenone group in either the sn-1 or sn-2 chain of an oleoyl-type ester or oleyl-type ether chain and P-32 in the phosphate group were synthesized. The benzophenone moiety was introduced by selective hydroboration of the double bond of enyne 11 at low temperature, followed by a Suzuki reaction with 4-bromobenzophenone. The key intermediates for the preparation of ester-linked lysophosphatidic acid (LPA) I and 3 were obtained in one pot by a modified DIBAL-H reduction of orthoformate intermediate 22. These probes were shown to covalently modify a single protein target in rat plasma containing albumin and several protein targets in rat plasma containing a low level of albumin.

  DOI：

  10.1021/jo052030w