6-azidohex-2-yn-1-ol | 128773-83-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-azidohex-2-yn-1-ol
• CAS: 128773-83-1
• 化学式: C₆H₉N₃O
• 分子量: 139.157
• InChiKey: BOYDDJWFDGZOIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-azidohex-2-yn-1-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以2.45 g的产率得到(E)-6-aminohex-2-en-1-ol
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts

  摘要：

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.

  DOI：

  10.1021/jo050171s
• 作为产物：
  描述：

  2-((6-bromohex-2-yn-1-yl)oxy)tetrahydro-2H-pyran 在 sodium azide 、 对甲苯磺酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 6-azidohex-2-yn-1-ol
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts

  摘要：

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.

  DOI：

  10.1021/jo050171s

文献信息

• Enantioselective Synthesis of Pyrrolidine-, Piperidine-, and Azepane-Type <i>N</i>-Heterocycles with α-Alkenyl Substitution: The CpRu-Catalyzed Dehydrative Intramolecular <i>N</i>-Allylation Approach
  作者：Tomoaki Seki、Shinji Tanaka、Masato Kitamura

  DOI：10.1021/ol203218d

  日期：2012.1.20

  acid derivatives [(R)- or (S)-Cl-Naph-PyCOOCH2CH═CH2] catalyzes asymmetric intramolecular dehydrative N-allylation of N-substituted ω-amino- and -aminocarbonyl allylic alcohols with a substrate/catalyst ratio of up to 2000 to give α-alkenyl pyrrolidine-, piperidine-, and azepane-type N-heterocycles with an enantiomer ratio of up to >99:1. The wide range of applicable N-substitutions, including Boc, Cbz

  阳离子CPRU复杂的手性吡啶甲酸衍生物[（的[R ）-或（小号）-Cl-的Naph-PyCOOCH 2 CH = CH 2 ]催化不对称分子内脱水Ñ的-allylation Ñ取代ω氨基-和氨基羰基烯丙基醇底物/催化剂比例最高为2000，可得到对映体比例最高> 99：1的α-烯基吡咯烷-，哌啶-和氮杂环庚烷型N-杂环。广泛适用的N取代基，包括Boc，Cbz，Ac，Bz，丙烯酰基，巴豆酰基，甲酰基和Ts，极大地促进了对天然产物合成的进一步控制。
• Construction of Azacycles Based on Endo-Mode Cyclization of Allenes
  作者：Chisato Mukai、Minoru Kobayashi、Shoko Kubota、Yukie Takahashi、Shinji Kitagaki

  DOI：10.1021/jo035729f

  日期：2004.3.1

  procedure for constructing monocyclic five- and six-membered azacycles by the endo-mode ring-closing reaction of allenylazido derivatives under neutral conditions has been developed. The azabicyclo[m.n.0] compounds were prepared by applying this newly developed procedure. The seven-membered azacycle was prepared when the allene possessing an unsubstituted carboxyl amido functionality was submitted

  已开发出一种在中性条件下通过烯丙基叠氮基衍生物的内模闭环反应构建单环五元和六元氮杂环的新方法。氮杂双环[ m。Ñ通过施加该新开发的方法制备0.0]的化合物。当具有未取代的羧基酰胺基官能团的丙二烯经受基本条件时，制备了七元氮杂环。另外，使用该方法合成了吲哚和喹啉骨架。
• Fluorescent SAM analogues for methyltransferase based DNA labeling
  作者：Vince Goyvaerts、Sven Van Snick、Laurens D'Huys、Raffaele Vitale、Milena Helmer Lauer、Su Wang、Volker Leen、Wim Dehaen、Johan Hofkens

  DOI：10.1039/c9cc08938a

  日期：——

  In this work, the preparation of new S-adenosyl-l-methionine (SAM) analogues for sequence specific DNA labeling is evaluated. Fluorescent cofactors were synthesized and their applicability in methyltransferase based optical mapping is demonstrated.

  在这项工作中，评估了新的S-腺苷-1-甲硫氨酸（SAM）类似物用于序列特异性DNA标记的制备。合成了荧光辅因子，并展示了它们在基于甲基转移酶的光学映射中的适用性。
• The Synthesis of Triazole Analogues of Antitumor Dehydropyrrolizidine Alkaloids
  作者：William H. Pearson、Stephen C. Bergmeier、Jayne A. Chytra

  DOI：10.1055/s-1990-26820

  日期：——

  Several mono- and disubstituted 5,6-dihydro-4H-pyrrolo[1,2-c] [1,2,3]triazoles have been prepared via intramolecular 1,3-dipolar cycloadditions of azides with alkynes. These triazoles are analogues of the antitumor dehydropyrrolizidine alkaloids.

  几种单取代和二取代的5,6-二氢-4H-吡咯并[1,2-c][1,2,3]三唑已通过叠氮化物与炔的分子内1,3-偶极环加成制备。这些三唑是抗肿瘤脱氢吡咯里西啶生物碱的类似物。
• 10.1021/jacs.4c06529
  作者：Gasiulė, Liepa、Stankevičius, Vaidotas、Kvederavičiu̅tė, Kotryna、Rimšelis, Jonas Mindaugas、Klimkevičius, Vaidas、Petraitytė, Gražina、Rukšėnaitė, Audronė、Masevičius, Viktoras、Klimašauskas, Saulius

  DOI：10.1021/jacs.4c06529

  日期：——

  transferable group from the corresponding precursors have been exploited. Here, we used structure-guided engineering of mouse MAT2A to enable biocatalytic production of an extended AdoMet analogue, Ado-6-azide, from a synthetic methionine analogue, S-(6-azidohex-2-ynyl)-l-homocysteine (N3-Met). Three engineered MAT2A variants showed catalytic proficiency with the extended analogues and supported DNA

  甲基化是一种广泛存在的天然修饰，具有多种调节和结构功能，由多种S-腺苷-L-甲硫氨酸 (AdoMet) 依赖性甲基转移酶 (MTase) 进行。 AdoMet 辅因子由多聚体蛋氨酸腺苷转移酶 (MAT) 家族从L-蛋氨酸 (Met) 和 ATP 产生。为了推进机制和功能研究，已经开发了重新利用 MAT 和 MTase 反应以接受来自相应前体的可转移基团的扩展版本的策略。在这里，我们使用小鼠 MAT2A 的结构引导工程，从合成蛋氨酸类似物S -(6-azidohex-2-ynyl)- l -homocysteine (N 3 -Met）。三种工程化 MAT2A 变体显示出对扩展类似物的催化能力，并在存在和不存在竞争性 Met 的情况下支持与M.Taq I 和小鼠 DNMT1 工程化变体的级联反应中的 DNA 衍生化。然后，我们使用 CRISPR-Cas 基因组编辑将两个工程变体作为 MAT2A-DNMT1