(E)-[2-¹³C]-4-(benzyloxy)but-2-en-1-ol | 114694-39-2

• 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: (E)-[2-¹³C]-4-(benzyloxy)but-2-en-1-ol
• 英文别名: [2-13C]-(E)-4-benzyloxy-but-2-en-1-ol；(E)-4-phenylmethoxy(213C)but-2-en-1-ol
• CAS: 114694-39-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 179.22
• InChiKey: CGLJRLXTVXHOLX-KFLNGZJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-[2-¹³C]-4-(benzyloxy)but-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 生成 、
  参考文献：
  名称：

  Regioselective synthesis of 13C1-labeled 2-deoxyribonolactones

  摘要：

  Syntheses of the five regioselectively C-13(1)-labeled 5-O-benzyl-2-deoxyribonolactones are described. C-13(1)-Labeled deoxyribonolactones were prepared by addition of KCN to epoxides 7 and subsequent lactonization of the resulting nitriles. Integration of the independent schemes leading to the five isotopomers of 9 results in an efficient and cost effective preparation of labeled mixtures of C-13 mono-labeled deoxyribonolactones. These mixtures are the pivotal intermediates in the preparation of 'population labeled' C-13-labeled nucleoside phosphoramidites for solid-phase oligonucleotide synthesis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01148-0
• 作为产物：
  描述：

  苄氧基乙醛 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 0.17h， 生成 (E)-[2-¹³C]-4-(benzyloxy)but-2-en-1-ol
  参考文献：
  名称：

  Regioselective synthesis of 13C1-labeled 2-deoxyribonolactones

  摘要：

  Syntheses of the five regioselectively C-13(1)-labeled 5-O-benzyl-2-deoxyribonolactones are described. C-13(1)-Labeled deoxyribonolactones were prepared by addition of KCN to epoxides 7 and subsequent lactonization of the resulting nitriles. Integration of the independent schemes leading to the five isotopomers of 9 results in an efficient and cost effective preparation of labeled mixtures of C-13 mono-labeled deoxyribonolactones. These mixtures are the pivotal intermediates in the preparation of 'population labeled' C-13-labeled nucleoside phosphoramidites for solid-phase oligonucleotide synthesis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01148-0

文献信息

• Highly Efficient Preparation of Selectively Isotope Cluster-Labeled Long Chain Fatty Acids via Two Consecutive C_sp³–C_sp³ Cross-Coupling Reactions
  作者：Sébastien Lethu、Shigeru Matsuoka、Michio Murata

  DOI：10.1021/ol4036159

  日期：2014.2.7

  An efficient synthesis involving two copper-catalyzed alkyl–alkyl coupling reactions has been designed to easily access doubly isotope-labeled fatty acids. Such NMR- and IR-active compounds were obtained in excellent overall yields and will be further used for determining the conformation of an alkyl chain of lipidic biomolecules upon interaction with proteins.

  设计了一种有效的合成方法，涉及两个铜催化的烷基-烷基偶联反应，可轻松获得双同位素标记的脂肪酸。这样的NMR-和IR-活性化合物以优异的总收率获得，并且将进一步用于确定脂质生物分子与蛋白质相互作用时烷基链的构象。