Z-[3-2H]-allyl alcohol | 78370-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Z-[3-2H]-allyl alcohol
• 英文别名: trans-<3-²H>allyl alcohol；E-<3-²H>-allyl alcohol；(E)-3-Deuterioallyl alcohol；allylic alcohol-trans-3-d；(E)-prop-2-en-3-d-1-ol；trans-[3-²H]allyl alcohol
• CAS: 78370-38-4
• 化学式: C₃H₆O
• 分子量: 59.0721
• InChiKey: XXROGKLTLUQVRX-GXFUBBPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  4.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Z-[3-2H]-allyl alcohol 在 银 氧气 作用下， 生成 acrolein-trans-3-d
  参考文献：
  名称：

  Molecular structure of s-cis- and s-trans-acrolein determined by microwave spectroscopy

  摘要：

  DOI：

  10.1021/ja00336a022
• 作为产物：
  描述：

  2-丙炔-1-醇 在 lithium aluminium tetrahydride 作用下， 以 水 为溶剂， 生成 Z-[3-2H]-allyl alcohol
  参考文献：
  名称：

  Effets isotopiques dudeutériumen RMN 13 C，量度du alquage isotopique des alcools烯丙基。

  摘要：

  据报道十二种烯丙醇对13 C NMR化学位移的三角化学碳的一级和二级氘同位素影响。次级DIECCS用于精确测量各种取代的烯丙醇的氘标记。

  DOI：

  10.1016/s0040-4039(00)80389-5

文献信息

• Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of <i>N</i>-Alloc Ynamides
  作者：Juliana R. Alexander、Matthew J. Cook

  DOI：10.1021/acs.orglett.7b02780

  日期：2017.11.3

  A new approach for the formation of ketenimines via a decarboxylative allylic rearrangement pathway that does not require strong stabilizing or protecting groups has been developed. The products can be readily hydrolyzed into their corresponding secondary amides or reacted with sulfur ylides to perform an additional [2,3]-Wittig process. Mechanistic studies suggest an outer-sphere process in which

  已经开发了通过脱羧基的烯丙基重排途径形成酮亚胺的新方法，该方法不需要强的稳定基团或保护基团。产物可以容易地水解成它们相应的仲酰胺或与硫酰化物反应以进行另外的[2，3] -Wittig方法。机理研究表明，其中还原烷基化是限速的外球过程。
• Assay for the Enantiomeric Analysis of [²H₁]-Fluoroacetic Acid:  Insight into the Stereochemical Course of Fluorination during Fluorometabolite Biosynthesis in <i>Streptomyces cattleya</i>
  作者：David O'Hagan、Rebecca J. M. Goss、Abdelkrim Meddour、Jacques Courtieu

  DOI：10.1021/ja026654k

  日期：2003.1.1

  analysis of (R)- and (S)-[2H1]-fluoroacetate has been developed using 2H[1H]-NMR in a chiral liquid crystalline solvent. This has enabled biosynthetic experiments to be conducted which reveal stereochemical details on biological fluorination occurring during the biosynthesis of fluoroacetate and 4-fluorothreonine in the bacterium Streptomyces cattleya. In particular, feeding experiments to S. cattleya

  在手性液晶溶剂中使用 2H[1H]-NMR 开发了一种用于 (R)-和 (S)-[2H1]-氟乙酸酯构型分析的灵敏方法。这使得能够进行生物合成实验，揭示在细菌 Streptomyces catyaya 中氟乙酸盐和 4-氟苏氨酸的生物合成过程中发生的生物氟化的立体化学细节。特别是，用同位素标记的 (1R, 2R)- 和 (1S, 2R)-[1-2H1]-甘油 3d 和 3e 和 [2,3-2H(4)]-琥珀酸酯 4a 对 S. catalya 进行饲养实验，得到上升到对映体富集的 [2-2H1]-氟乙酸盐样品 1a。
• A short synthesis of (1S,2R)- and (1R,2R)-[1-2H]-glycerols
  作者：Jens Nieschalk、David O'Hagan

  DOI：10.1016/s0957-4166(97)00219-x

  日期：1997.7

  (1S,2R)- and 1a and 1b is reported. The key asymmetric step involves an AD-mix-β dihydroxylation on deuterium labelled Z- and E-allyl benzoates 4a and 4b. The route should facilitate the use of [2H]-glycerols 1a−1d in high enantiomeric purity (95%ee) in biosynthesis investigations.

  报告了一个简单的三步路线，到达（1 S，2 R）-和1a和1b。关键的不对称步骤涉及在氘标记的Z-和E-烯丙基苯甲酸酯4a和4b上进行AD-mix-β二羟基化。该途径应有助于在生物合成研究中使用高对映体纯度（95％ee）的[ 2 H]-甘油1a-1d。
• Bergens, Steven H.; Noheda, Pedro; Whelan, John, Journal of the American Chemical Society, 1992, vol. 114, # 6, p. 2128 - 2135
  作者：Bergens, Steven H.、Noheda, Pedro、Whelan, John、Bosnich

  DOI：——

  日期：——
• Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile
  作者：Haitao Zhu、Pinhong Chen、Guosheng Liu

  DOI：10.1021/ja412023b

  日期：2014.2.5

  A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (S(N)2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.