ethyl (3R,4E)-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enoate | 1007220-96-3

• 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: ethyl (3R,4E)-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enoate
• 英文别名: ethyl (E,3R)-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enoate
• CAS: 1007220-96-3
• 化学式: C₁₄H₂₅BO₄
• 分子量: 268.161
• InChiKey: ZPRMXENZYRKDPF-FBOQAHMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (3R,4E)-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enoate 、 2-[(1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl]-1,3,3-trimethylcyclohex-1-ene 在 四(三苯基膦)钯 氢氧化铊(Ⅰ) 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 以55%的产率得到ethyl (13R)-13,14-dihydroretinoate
  参考文献：
  名称：

  Stereospecificity of Retinol Saturase:  Absolute Configuration, Synthesis, and Biological Evaluation of Dihydroretinoids

  摘要：

  Retinol saturase carries out a stereospecific saturation of the C13-C14 double bond of all-trans-retinol to generate (13R)-all-trans-13,14-dihydroretinol. This compound is found in cells expressing mouse or zebrafish retinol saturase and in the livers of mice fed retinyl palmitate. All-trans-13,14-dihydroretinol is oxidized in vivo to all-trans-13,14-dihydroretinoic acid, a highly selective agonist of the retinoic acid receptor. The naturally occurring (13R)-all-trans-13,14-dihydroretinoic acid is a weaker agonist than the (13S) enantiomer, indicating enantioselective recognition by the ligand-binding pocket of this receptor. Consequently the (13S) enantiomer, acting through the retinoic acid receptor, also inhibits adipose differentiation more potently than the (13R) enantiomer.

  DOI：

  10.1021/ja710487q
• 作为产物：
  描述：

  ethyl (3R)-3-methyl-4-oxobutanoate 、 频哪醇(二氯甲基)硼酸酯 在 lithium iodide chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以68%的产率得到ethyl (3R,4E)-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enoate
  参考文献：
  名称：

  WO2008/63768

  摘要：

  公开号：

文献信息

• WO2008/63768
  申请人：——

  公开号：——

  公开（公告）日：——
• Stereospecificity of Retinol Saturase:  Absolute Configuration, Synthesis, and Biological Evaluation of Dihydroretinoids
  作者：Alexander R. Moise、Marta Domínguez、Susana Alvarez、Rosana Alvarez、Michael Schupp、Ana G. Cristancho、Philip D. Kiser、Angel R. de Lera、Mitchell A. Lazar、Krzysztof Palczewski

  DOI：10.1021/ja710487q

  日期：2008.1.30

  Retinol saturase carries out a stereospecific saturation of the C13-C14 double bond of all-trans-retinol to generate (13R)-all-trans-13,14-dihydroretinol. This compound is found in cells expressing mouse or zebrafish retinol saturase and in the livers of mice fed retinyl palmitate. All-trans-13,14-dihydroretinol is oxidized in vivo to all-trans-13,14-dihydroretinoic acid, a highly selective agonist of the retinoic acid receptor. The naturally occurring (13R)-all-trans-13,14-dihydroretinoic acid is a weaker agonist than the (13S) enantiomer, indicating enantioselective recognition by the ligand-binding pocket of this receptor. Consequently the (13S) enantiomer, acting through the retinoic acid receptor, also inhibits adipose differentiation more potently than the (13R) enantiomer.