(2R,6R)-2,6-二烯丙基-1,2,3,6-四氢吡啶 | 138617-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (2R,6R)-2,6-二烯丙基-1,2,3,6-四氢吡啶
• 英文名称: trans-2,6-diallyl-1,2,3,6-tetrahydropyridine
• 英文别名: trans-2,6-diallyl-1,2,5,6-tetrahydropyridine；trans-2,6-diallyl-3-piperidine；(2R,6R)-2,6-Diallyl-1,2,3,6-tetrahydropyridine；(2R,6R)-2,6-bis(prop-2-enyl)-1,2,3,6-tetrahydropyridine
• CAS: 138617-50-2
• 化学式: C₁₁H₁₇N
• 分子量: 163.263
• InChiKey: GAYQJEALDMVJON-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,6R)-2,6-二烯丙基-1,2,3,6-四氢吡啶 在 三烯丙基硼烷 、 甲醇 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以94%的产率得到
  参考文献：
  名称：

  基于 N-单-和 N,N-双-3-丁烯基二氯乙酰胺的新型玉米生长调节剂

  摘要：

  亚胺、腈（包括氢氰酸）、酰胺、内酰胺、芳香氮杂杂环（吡啶、异喹啉和吡咯）的烯丙基硼化被用于合成一系列不同结构的单-和双-3-丁烯胺，将其转化为二氯乙酰胺，一种已知安全剂（除草剂解毒剂）的新类似物二氯杀螨酯已成功用于世界各地的玉米种植。玉米种子发芽生物学试验表明，所得二氯乙酰胺大部分具有促生长活性，主要针对根系发育。化合物 2f、反式和顺式 2n、顺式 2s 和 2t 表现出出色的活性，超过敌草畏对玉米幼苗发育根系的刺激作用的 2 到 3 倍。

  DOI：

  10.1007/s11172-018-2080-0
• 作为产物：
  描述：

  Pyridin-triallylbor-Addukt 在 甲醇 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (2R,6R)-2,6-二烯丙基-1,2,3,6-四氢吡啶
  参考文献：
  名称：

  Reductive 2,6-trans-diallylation of pyridine by triallylborane

  摘要：

  DOI：

  10.1007/bf00961061

文献信息

• Stereoselective synthesis of (±)-indolizidines 167B and 209D and theirtrans-isomers based on the reductive allylboration of pyridine
  作者：Yu. N. Bubnov、E. V. Klimkina、A. V. Ignatenko

  DOI：10.1007/bf02498166

  日期：1998.5

  intramolecular cyclization oftrans- andcis-2-allyl-6-R-1,2,3,6-tetrahydropyridines, obtained from pyridine and triallylborane, has been elaborated. The closure of the five-membered ring is carried out by hydroboration-oxidation followed by cyclization of the resulting δ-amino alcohols in the presence of the Ph3P−CBr4−Et3N system. (Pr2BH)2 and Pr3B are used as the hydroborating reagents, and H2O2 in an acid medium

  已经详细阐述了基于反式和顺式-2-烯丙基-6-R-1,2,3,6-四氢吡啶的分子内环化合成 5-取代吲哚里西啶的一般方法，该方法从吡啶和三烯丙基硼烷中获得。五元环的闭合是通过硼氢化-氧化然后在 Ph3P-CBr4-Et3N 系统存在下将所得 δ-氨基醇环化来进行的。(Pr2BH)2 和 Pr3B 用作硼氢化试剂，在酸性介质中用 H2O2 氧化形成的 2-[3-(二丙基硼基]-Δ2-哌啶。该方法已用于合成两种天然生物碱类：分别由cis-和trans-2-allyl-6-hexyl-1,2,3,6-tetrahydropiridine制备吲哚里西啶209D（cis-5-hexylindolizidine）及其反式异构体；
• Reductivetrans-2,6-diallylation of pyridines with allylboranes. Synthesis oftrans- andcis-2,6-diallyl-1,2,5,6-tetrahydropyridines and their deuterated derivatives
  作者：Yu. N. Bubnov、E. A. Shagova、S. V. Evchenko、A. V. Ignatenko

  DOI：10.1007/bf00699842

  日期：1994.4

  The reductive trans-2,6-diallylation of pyridines with triallyl- and allyI(dialkyl)boranes has been discovered. Heating (40-100 degrees C) of pyridine, deuteropyridine, or 3-bromopyridine complexes with triallylborane in the presence of alcohols (ROH or CH3OD), water, or Et(2)NH results in the respective trans-2,6-diallyl-1,2,5,6-tetrahydropyridines (2, 3, 22, or 25) In 20-97% yields. A preparative method for the isomerization of trans-2,6-diallyl compounds 2 and 25 into the respective cis-isomers 4 and 28 by heating them with triallyl- or allyl(dialkyl)boranes (125-150 degrees C) has been suggested. The hydrogenation of trans- or cis-2,6-diallyl-1,2,5,6-tetrahydropyridines gave trans- or cis-2,6-dipropylpiperidines, respectively. The cis- and trans-configurations of compounds 2 and 4 were established by analyzing the NMR spectra of N-benzyl (7 and 13) and N,N-dimethyl (6 and 14) derivatives of piperidine derivatives 5 and 8. A possible mechanism for the reductive diallylation of pyridines has been discussed.
• ——
  作者：L. M. Korotayeva、T. Ya. Rubinskaya、E. V. Klimkina、V. P. Gultyai、Yu. N. Bubnov

  DOI：10.1023/a:1009580110623

  日期：——

  Electrochemical reduction of trans-2-allyl-6-R-1,2,3,6-tetrahydropyridines (R = Me, All, and Ph) on the mercury cathode in anhydrous DMF (with 0.1 M Bu4NClO4 as the supporting electrolyte) resulted in catalytic hydrogen evolution, while in the case of anhydrous DMF the electrochemical activity of the endocyclic double bond was dictated by the nature of the R substituent at the carbon atom neighboring the double bond. The electrocatalytic hydrogenation of the piperideines under study on the Ni (Ni-disp/Ni) cathode in 40%; aqueous DMF in the presence of a tenfold excess of AcOH yielded the corresponding trans-2-propyl-6-R-1 piperidines (R-1 = Me, Pr, acid Ph). Using trans-2,6-diallyl-1,2,3,6-tetrahydropyridine as an example, the conditions (with annealed copper as the cathode) for selective hydrogenation of the double bonds in allyl substituents with preservation of the endocyclic double bond were found.
• Thermaltrans-cis-isomerization oftrans-2,6-diallyl-?3-piperideiiie by the action of triallylborane
  作者：Yu. N. Bubnov、E. A. Shagova、S. V. Evchenko、A. V. Ignatenko

  DOI：10.1007/bf00699209

  日期：1993.9
• New growth regulators of corn based on N-mono- and N,N-bis-3-butenyldichloroacetamides
  作者：Yu. N. Bubnov、Yu. Ya. Spiridonov、N. Yu. Kuznetsov

  DOI：10.1007/s11172-018-2080-0

  日期：2018.2

  Allylboration of imines, nitriles (including hydrocyanic acid), amides, lactams, aromatic azaheterocycles (pyridines, isoquinoline, and pyrrole) was used to synthesize a series of mono- and bis-3-butenylamines with different structures, which were converted to dichloroacetamides, new analogs of a known safener (herbicide antidote) Dichlormid successfully used in the cultivation of corn throughout the

  亚胺、腈（包括氢氰酸）、酰胺、内酰胺、芳香氮杂杂环（吡啶、异喹啉和吡咯）的烯丙基硼化被用于合成一系列不同结构的单-和双-3-丁烯胺，将其转化为二氯乙酰胺，一种已知安全剂（除草剂解毒剂）的新类似物二氯杀螨酯已成功用于世界各地的玉米种植。玉米种子发芽生物学试验表明，所得二氯乙酰胺大部分具有促生长活性，主要针对根系发育。化合物 2f、反式和顺式 2n、顺式 2s 和 2t 表现出出色的活性，超过敌草畏对玉米幼苗发育根系的刺激作用的 2 到 3 倍。