3-triethylsiloxy-β-ionone | 473758-74-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-triethylsiloxy-β-ionone
• 英文别名: (E)-4-(2,6,6-trimethyl-4-triethylsilyloxycyclohexen-1-yl)but-3-en-2-one
• CAS: 473758-74-6
• 化学式: C₁₉H₃₄O₂Si
• 分子量: 322.563
• InChiKey: NFBDCHWUDUPWIQ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-triethylsiloxy-β-ionone 在 lithium aluminium tetrahydride 、 正丁基锂 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 3-triethylsiloxy-all-trans-retinol
  参考文献：
  名称：

  Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins

  摘要：

  The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-0]-all trans-retinol chloroacetate is described. These biotinylated retinoids a-re instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Homer-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00667-1
• 作为产物：
  描述：

  (3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 双氧水 、 对甲苯磺酸 、 三乙胺 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 6.08h， 生成 3-triethylsiloxy-β-ionone
  参考文献：
  名称：

  Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins

  摘要：

  The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-0]-all trans-retinol chloroacetate is described. These biotinylated retinoids a-re instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Homer-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00667-1

文献信息

• Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins
  作者：Nasri Nesnas、Robert R Rando、Koji Nakanishi

  DOI：10.1016/s0040-4020(02)00667-1

  日期：2002.8

  The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-0]-all trans-retinol chloroacetate is described. These biotinylated retinoids a-re instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Homer-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. (C) 2002 Elsevier Science Ltd. All rights reserved.