undec-2-yn-1-ol | 34683-71-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: undec-2-yn-1-ol
• 英文别名: 2-undecyn-1-ol
• CAS: 34683-71-1
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: BRZOPVQIKCYZBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2905290000

反应信息

• 作为反应物：
  描述：

  undec-2-yn-1-ol 在 palladium on activated charcoal 正丁基锂 、 硫酸 、 氢溴酸 、 氢气 、 sodium hydride 、 乙二胺 作用下， 以 乙醇 为溶剂， 生成 1-tetracosyl bromide
  参考文献：
  名称：

  Hyperextended amphiphiles. Bilayer formation from single-tailed compounds

  摘要：

  DOI：

  10.1021/ja00062a086
• 作为产物：
  描述：

  1-tetrahydropyranyloxy-n-2-dodecyn 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 undec-2-yn-1-ol
  参考文献：
  名称：

  Evaluation of the Key Aroma Compounds in Beef and Pork Vegetable Gravies a la Chef by Stable Isotope Dilution Assays and Aroma Recombination Experiments

  摘要：

  Although the aroma compounds of meat processed as such have been studied previously, data on complete homemade dishes containing beef and pork meat were scarcely studied. Recently, 38 odor-active compounds were characterized in beef and pork vegetable gravies using GC-olfactometry. In the present investigation, the most odor-active compounds were quantitated in a freshly prepared stewed beef vegetable gravy (BVG) as well as a stewed pork vegetable gravy (PVG) by means of stable isotope dilution assays. Calculation of odor activity values (OAVs; ratio of concentration to odor threshold) revealed 3-mercapto-2-methylpentan-1-ol, (E,E)-2,4-decadienal, (E,Z)-2,6-nonadienal, (E)-2-decenal, (E)-2-undecanal, and 3-hydroxy-4,5-dimethyl-2(5H)-furanone as the most potent odorants in both gravies. However, significantly different OAVs were found for 12-methyltridecanal, which was much higher in the BVG, whereas (E,Z)-2,4-decadienal showed a clearly higher OAV in the PVG. Aroma recombination experiments performed on the basis of the actual concentrations of the odorants in both gravies revealed a good similarity of the aromas of both model mixtures containing all odorants with OAVs > 1 with those of the original gravies.

  DOI：

  10.1021/jf203340a

文献信息

• Enantioselective Rhodium-Catalyzed Atom-Economical Macrolactonization
  作者：Stephanie Ganss、Bernhard Breit

  DOI：10.1002/anie.201604301

  日期：2016.8.8

  coupling of ω‐allenyl‐substituted carboxylic acids. The use of a modified diop ligand, chiral DTBM‐diop, led to high enantioselectivity (up to 93 % ee). The reaction tolerated a large variety of functionalities, including α,β‐unsaturated carboxylic acids and depsipeptides, and provided the desired macrocycles with very high enantio‐ and diastereoselectivity.

  描述了形成大内酯的高度吸引人的途径，大内酯形成多种多样的天然化合物的环状支架。尽管已经探索了许多针对该结构基序的化学方法，但是环化的不对称变体是前所未有的。在这里，我们通过ω-烯基取代的羧酸的分子内原子-经济铑催化的偶合来呈现对映选择性大内酯化作用。使用改良的二重配体，手性DTBM二联体，可实现高对映选择性（高达93％  ee）。该反应可耐受多种功能，包括α，β-不饱和羧酸和二肽，并提供所需的具有高对映体和非对映体选择性的大环。
• Highly regioselective gold-catalyzed formal hydration of propargylic <i>gem</i>-difluorides
  作者：Jean-Denys Hamel、Tatsuru Hayashi、Mélissa Cloutier、Paul R. Savoie、Olivier Thibeault、Meggan Beaudoin、Jean-François Paquin

  DOI：10.1039/c7ob02406a

  日期：——

  Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility

  在本文中，我们报道了炔丙基宝石-二氟化物的高度区域选择性金催化的正式水合。这种转化不仅提供了难以或几乎不可能预先获得的多用途氟化结构单元的途径，而且还代表了内部炔烃具有高度区域选择性的金催化加氢烷氧基化的罕见情况，并提出了二氟亚甲基单元的实用性。催化中的指导基团。
• Hydrogen-Bond-Promoted Friedel–Crafts Reaction of Secondary Propargylic Fluorides: Preparation of 1-Alkyl-1-aryl-2-alkynes
  作者：Jean-Denys Hamel、Meggan Beaudoin、Mélissa Cloutier、Jean-François Paquin

  DOI：10.1055/s-0036-1589057

  日期：2017.12

  We report that aromatic propargylation is achievable with secondary propargylic fluorides, thus affording 1-alkyl-1-aryl-2-alkynes. In the present case, hydrogen bonding is responsible for the activation of the C–F bond. A large excess of arene nucleophile is shown to be necessary to achieve good yields.

  我们报告说，芳族炔丙基化可以用仲炔丙基氟化物实现，从而提供 1-烷基-1-芳基-2-炔烃。在目前的情况下，氢键负责激活 C-F 键。大量过量的芳烃亲核试剂被证明是获得良好收率所必需的。
• Aryl aliphatic acids
  申请人：Board of Governors of Wayne State University

  公开号：US05238832A1

  公开（公告）日：1993-08-24

  Novel aryl aliphatic acids or derivatives thereof of the general formula R--(C.sub.x --C.sub.y)--(C.sub.m H.sub.2m)--G--C(R.sup.1).sub.2 --Ar--(C.sub.n H.sub.2n)--COOR.sup.2 are described which exhibit inhibiting activity against 12-lipoxygenase. The compounds are characterized by having a low level of toxicity. Also included are salts and esters of the aliphatic acids.

  题目描述了一种具有抑制12-脂氧合酶活性的新型芳基脂肪羧酸或其衍生物，具有低毒性，还包括这些脂肪酸的盐和酯。
• Enantioselective Synthesis and Antifungal Activity of C18 Polyacetylenes
  作者：Jia Liu、Shichao Lu、Jiayang Feng、Changkai Li、Wenliang Wang、Yiming Pei、Shengli Ding、Meng Zhang、Honglian Li、Risong Na、Qing X. Li

  DOI：10.1021/acs.jafc.9b07967

  日期：2020.2.19

  diseases and decrease crop yields and quality. Polyacetylene alcohols are plant secondary metabolites and bioactive against various pathogenic fungi. They are, however, difficult to synthesize. In the present study, an efficient and highly enantioselective method (>98% ee) was established and employed to achieve the synthesis of the natural C18 polyacetylenes (S,E)-octadeca-1,9-dien-4,6-diyn-3-ol 1, (3R

  真菌病原体会导致严重的农作物疾病，并降低农作物的产量和质量。聚乙炔醇是植物的次生代谢产物，对各种病原真菌具有生物活性。但是，它们很难合成。在本研究中，建立了一种高效且高对映选择性的方法（> 98％ee），并采用该方法实现了天然C18聚乙炔（S，E）-octadeca-1,9-dien-4,6-diyn-的合成3-醇1，（3R，10R，E）-十八烷基-1,8-二烯-4,6-二炔-3,10-二醇2及其类似物。对标题化合物进行结构表征并对其杀真菌活性进行生物学评估。这些化合物对8种病原真菌具有很高的功效，这些物种例如炭疽菌，双极双孢菌，镰刀镰刀菌和假镰刀菌，其最大有效浓度的一半为8至425μg/ mL，与杀真菌剂甲基硫氰酸酯（3-408μg/ mL）相似。这些化合物是潜在的天然杀真菌剂和杀真菌剂的潜在候选者，可用于进一步改善结构和性能。