3-hydroxy-β-ionone | 142739-16-0

• 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-hydroxy-β-ionone
• CAS: 142739-16-0
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: BJYHHNGXAVKJGT-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-β-ionone 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.08h， 生成 3-triethylsiloxy-all-trans-retinoic acid ethyl ester
  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：

  在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 3-hydroxy-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 (±)-E-(1,2,4-trihydroxy-2,6,6-tirmethylcyclohexyl)-but-3-en-2-one: A novel degraded carotenoid isolated from New Zealand thyme (thymus vulgaris) honey
  作者：Susan J. Broom、Richard M. Ede、Alistair L. Wilkins

  DOI：10.1016/s0040-4039(00)79850-9

  日期：1992.5

  A racemic synthesis of the title compound is described starting from β-ionone. The key steps involve selective hydroboration of a triene, followed by molybdenum mediated epoxidation of the resulting homoallylic alcohol with subsequent ring opening of the epoxide to give the title compound.

  从β-紫罗兰酮开始描述了标题化合物的外消旋合成。关键步骤包括三烯的选择性氢硼化，然后由钼介导的所得均烯丙基醇的环氧化，随后环氧化物的开环，得到标题化合物。
• Synthesis and binding studies of a photoaffinity label for bovine rhodopsin
  作者：Ranjan Sen、John D. Carriker、Valeria Balogh-Nair、Koji Nakanishi

  DOI：10.1021/ja00375a048

  日期：1982.6