1-(4-methoxyphenoxy)-3-(methoxymethoxy)-propan-(2R)-2-ol | 1028259-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenoxy)-3-(methoxymethoxy)-propan-(2R)-2-ol
• 英文别名: (2S)-1-(methoxymethoxy)-3-(4-methoxyphenoxy)propan-2-ol
• CAS: 1028259-29-1
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: OBWSSYKHIJOFDY-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenoxy)-3-(methoxymethoxy)-propan-(2R)-2-ol 在 ammonium cerium(IV) nitrate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 1-O-methoxymethyl-2-O-(13-(4-benzoylphenyl)-9-(Z)-tridecenoyl)-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：

  (R)-3-(p-methoxyphenoxy)-1,2-propanediol 在 camphor-10-sulfonic acid 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 1-(4-methoxyphenoxy)-3-(methoxymethoxy)-propan-(2R)-2-ol
  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.