1,1-dideuterocinnamyl alcohol | 59481-69-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 1,1-dideuterocinnamyl alcohol
• 英文别名: [1,1-(2)H2]-cinnamyl alcohol；1,1-dideuterio-3-phenyl-prop-2-en-1-ol；Cinnamylalkohol-1,1-d(2)
• CAS: 59481-69-5
• 化学式: C₉H₁₀O
• 分子量: 136.162
• InChiKey: OOCCDEMITAIZTP-MGVXTIMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1,1-dideuterocinnamyl alcohol 在 氢溴酸 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (αα-dideuteriocinnamyl)dimethyl-(3-phenylprop-2-ynyl)ammonium bromide
  参考文献：
  名称：

  涉及叶立德中间体的碱催化重排。第6部分。质子介质中二烯丙基和烯丙基丙炔基铵阳离子的重排

  摘要：

  水溶液中阳离子的碱催化重排（1d–j）产生异构阳离子（15）或醛（10）和（11）或（15），（10）和（11）的混合物。这与在质子惰性溶剂中观察到的阳离子（1）的转化形成鲜明对比。阳离子（15）进行霍夫曼消除成萘胺（12）或（13）和（14）。胺的甲硫脲（13克）显示出旋转受限的新结果。甲硫酮的nmr光谱表明，亚甲基的两个质子是非对映体。

  DOI：

  10.1039/p19800001477
• 作为产物：
  描述：

  肉桂酸乙酯 在 lithium aluminium deuteride 作用下， 以1.11 g的产率得到1,1-dideuterocinnamyl alcohol
  参考文献：
  名称：

  Characterization of the Key Aroma Compounds in Pink Guava (Psidium guajava L.) by Means of Aroma Re-engineering Experiments and Omission Tests

  摘要：

  Seventeen aroma-active volatiles, previously identified with high flavor dilution factors in fresh, pink Colombian guavas (Psidium guajava L.), were quantified by stable isotope dilution assays. On the basis of the quantitative data and odor thresholds in water, odor activity values (OAV; ratio of concentration to odor threshold) were calculated. High OAVs were determined for the green, grassy smelling (Z)-3-hexenal and the grapefruit-like smelling 3-sulfanyl-1-hexanol followed by 3-sulfanylhexyl acetate (black currant-like), hexanal (green, grassy), ethyl butanoate (fruity), acetaldehyde (fresh, pungent), trans-4,5-epoxy-(E)-2-decenal (metallic), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel, sweet), cinnamyl alcohol (floral), methyl (2S,3S)-2-hydroxy-3-methylpentanoate (fruity), cinnamyl acetate (floral), methional (cooked potato-like), and 3-hydroxy-4,5-dimethyl-2(5H)-furanone (seasoning-like). Studies on the time course of odorant formation in guava puree or cubes, respectively, showed that (2)-3-hexenal was hardly present in the intact fruits, but was formed very quickly during crushing. The aroma of fresh guava fruit cubes, which showed a very balanced aroma profile, was successfully mimicked in a reconstitute consisting of 13 odorants in their naturally occurring concentrations. Omission tests, in which single odorants were omitted from the entire aroma reconstitute, revealed (2)-3-hexenal, 3-sulfanyl-1-hexanol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-sulfanylhexyl acetate, hexanal, ethyl butanoate, cinnamyl acetate, and methional as the key aroma compounds of pink guavas.

  DOI：

  10.1021/jf803728n

文献信息

• Selenium-Catalyzed C(sp³)H Acyloxylation: Application in the Expedient Synthesis of Isobenzofuranones
  作者：Felix Krätzschmar、Martin Kaßel、Daniel Delony、Alexander Breder

  DOI：10.1002/chem.201406290

  日期：2015.5.4

  Oxidative Se‐catalyzed C(sp3)H bond acyloxylation has been used to construct a diverse array of isobenzofuranones from simple ortho‐allyl benzoic acid derivatives. The synthetic procedure employs mild reaction conditions and gives high chemoselectivity enabled by an inexpensive organodiselane catalyst. The presented approach offers a new synthetic pathway toward the core structures of phthalide natural

  氧化的Se催化的C（sp 3）H键酰氧基化已被用来从简单的邻烯丙基苯甲酸衍生物构造出各种各样的异苯并呋喃酮。合成过程采用温和的反应条件，并通过廉价的有机二硒烷催化剂实现了高化学选择性。提出的方法为邻苯二甲酰亚胺天然产物的核心结构提供了一条新的合成途径。
• Iridium‐Catalyzed Propenylation Reactions for the Synthesis of 4‐Pyridone Derivatives
  作者：Xue‐dan Bai、Jie Wang、Ying He

  DOI：10.1002/adsc.201801177

  日期：2019.2

  propenylation reaction of allylic carbonates with 4‐hydroxypyridine derivatives. The process efficiently provides 4‐pyridone derivatives with high stereoselectivities under mild conditions. The products could constitute valuable building blocks for the synthesis of natural products and other bioactive molecules. Preliminary mechanistic studies indicated that a tandem allylic substitution/isomerization

  在本文中，我们报道了烯丙基碳酸酯与4-羟基吡啶衍生物的铱催化丙烯基化反应。该方法可在温和条件下有效地提供具有高立体选择性的4-吡啶酮衍生物。这些产物可能构成合成天然产物和其他生物活性分子的有价值的组成部分。初步的机理研究表明，发生了串联烯丙基取代/异构化反应以提供丙烯基化产物。
• Iridium-Catalyzed Regio- and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization
  作者：Yusuke Ebe、Mitsuki Onoda、Takahiro Nishimura、Hideki Yorimitsu

  DOI：10.1002/anie.201702286

  日期：2017.5.8

  Iridium‐catalyzed hydroarylation of alkenyl ethers, such as allylic and homoallylic ethers, by C−H bond activation gave high yields of the corresponding addition products, where the aryl groups were selectively installed at the α‐carbon atom to the alkoxy group. The reaction involves an isomerization of the alkenyl ethers into the corresponding 1‐alkenyl ethers, which then undergo the regio‐ and enantioselective

  烯基醚（如烯丙基和均烯丙基醚）的铱催化的C-H键活化产生高产率的相应加成产物，其中芳基被选择性地安装在烷氧基的α-碳原子上。该反应涉及烯基醚异构化为相应的1-烯基醚，然后进行区域和对映选择性的氢芳基化。
• Manganese catalyzed cross-coupling of allylic alcohols and nitriles: an elegant route for access to δ-hydroxynitriles
  作者：Shiliang Wang、Dingguo Song、Feiyang Shen、Rong Chen、Yuqi Cheng、Chuhan Zhao、Qilei Shen、Shuxin Yin、Fei Ling、Weihui Zhong

  DOI：10.1039/d2gc03679g

  日期：——

  example of the pincer manganese(I) catalyzed redox-neutral coupling of nitriles with allylic alcohols to forge a variety of δ-hydroxynitriles. The reaction featured a broad substrate scope with good functional group tolerance under simple conditions (43 examples, 50–94% yields). Remarkably, the mildness and practicality of this protocol were further demonstrated by the successful synthesis of anipamil

  醇和腈衍生物是非常重要的骨架，广泛应用于有机和生物有机化学。由于其 100% 的原子经济性和易于获得的起始材料，通过形式共轭加成的醇和腈的交叉偶联是获得长碳链束缚腈的强大且环境友好的策略。在此，我们报道了钳形锰 ( I ) 催化腈与烯丙醇的氧化还原中性偶联以形成各种 δ-羟基腈的第一个例子。该反应在简单条件下具有广泛的底物范围和良好的官能团耐受性（43 个例子，50-94% 产率）。值得注意的是，阿尼帕米和维拉帕米的成功合成进一步证明了该协议的温和性和实用性通过一个或两个级联借氢程序。
• Characterization of the Key Aroma Compounds in Pink Guava (Psidium guajava L.) by Means of Aroma Re-engineering Experiments and Omission Tests
  作者：Martin Steinhaus、Diana Sinuco、Johannes Polster、Coralia Osorio、Peter Schieberle

  DOI：10.1021/jf803728n

  日期：2009.4.8

  Seventeen aroma-active volatiles, previously identified with high flavor dilution factors in fresh, pink Colombian guavas (Psidium guajava L.), were quantified by stable isotope dilution assays. On the basis of the quantitative data and odor thresholds in water, odor activity values (OAV; ratio of concentration to odor threshold) were calculated. High OAVs were determined for the green, grassy smelling (Z)-3-hexenal and the grapefruit-like smelling 3-sulfanyl-1-hexanol followed by 3-sulfanylhexyl acetate (black currant-like), hexanal (green, grassy), ethyl butanoate (fruity), acetaldehyde (fresh, pungent), trans-4,5-epoxy-(E)-2-decenal (metallic), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel, sweet), cinnamyl alcohol (floral), methyl (2S,3S)-2-hydroxy-3-methylpentanoate (fruity), cinnamyl acetate (floral), methional (cooked potato-like), and 3-hydroxy-4,5-dimethyl-2(5H)-furanone (seasoning-like). Studies on the time course of odorant formation in guava puree or cubes, respectively, showed that (2)-3-hexenal was hardly present in the intact fruits, but was formed very quickly during crushing. The aroma of fresh guava fruit cubes, which showed a very balanced aroma profile, was successfully mimicked in a reconstitute consisting of 13 odorants in their naturally occurring concentrations. Omission tests, in which single odorants were omitted from the entire aroma reconstitute, revealed (2)-3-hexenal, 3-sulfanyl-1-hexanol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-sulfanylhexyl acetate, hexanal, ethyl butanoate, cinnamyl acetate, and methional as the key aroma compounds of pink guavas.