1-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenoyl)-2-O-methoxymethyl-sn-glycerol | 874140-95-1

• 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: 1-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenoyl)-2-O-methoxymethyl-sn-glycerol
• 英文别名: [(2S)-3-hydroxy-2-(methoxymethoxy)propyl] (Z)-13-(4-benzoylphenyl)tridec-9-enoate
• CAS: 874140-95-1
• 化学式: C₃₁H₄₂O₆
• 分子量: 510.671
• InChiKey: DIYVOELPKUJGSG-BWMKHVPASA-N

物化性质

• 沸点：
  627.6±55.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  37
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenoyl)-2-O-methoxymethyl-sn-glycerol 在 乙二胺四乙酸 、 乙二醇双(2-氨基乙基醚)四乙酸 咪唑 、 diacylglycerol kinase 、 [32P]-ATP 作用下， 反应 2.0h， 生成 [(2R)-3-(32P)dihydroxy(32P)phosphoryloxy-2-(methoxymethoxy)propyl] (Z)-13-(4-benzoylphenyl)tridec-9-enoate
  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：

  2-(9-癸炔-1-基氧基)四氢-2H-吡喃 在 Lindlar's catalyst 重铬酸吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 偶氮二甲酸二异丙酯 、 氢气 、 4-甲基苯磺酸吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 77.0h， 生成 1-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenoyl)-2-O-methoxymethyl-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

文献信息

• Synthesis of Photoactivatable Analogues of Lysophosphatidic Acid and Covalent Labeling of Plasma Proteins
  作者：Zaiguo Li、Daniel L. Baker、Gabor Tigyi、Robert Bittman

  DOI：10.1021/jo052030w

  日期：2006.1.1

  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.