N-(2-methylpent-4-en-2-yl)hydroxylamine | 353244-61-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-methylpent-4-en-2-yl)hydroxylamine
• CAS: 353244-61-8
• 化学式: C₆H₁₃NO
• 分子量: 115.175
• InChiKey: GPMCTCLPGNLZAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 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：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-methylpent-4-en-2-yl)hydroxylamine 在 镍 盐酸 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0~90.0 ℃ 、1.0 MPa 条件下， 反应 112.0h， 生成 (1R,2R,3S,8R,9aR)-6,6-dimethyl-1,2,3,4,7,8,9,9a-octahydroquinolizine-1,2,3,8-tetrol
  参考文献：
  名称：

  Asymmetric synthesis of novel polyhydroxylated derivatives of indolizidine and quinolizidine by intramolecular 1,3-dipolar cycloaddition of N-(3-alkenyl)nitrones

  摘要：

  3-O-苄基-1,2-O-异亚丙基-1,5-戊二烯并-α-D-氧基呋喃糖与 N-（1,1-二甲基丁-3-烯基）羟基胺反应，然后进行分子内 1,3-二极环加成，得到 7-氧杂-1-氮杂双环[2.2.1]庚烷衍生物 4，很容易将其转化为新型多羟基喹嗪 6 和吲嗪 8。

  DOI：

  10.1039/b101057n
• 作为产物：
  描述：

  4-methyl-4-nitro-1-pentene 在 aluminium amalgam 作用下， 生成 N-(2-methylpent-4-en-2-yl)hydroxylamine
  参考文献：
  名称：

  Asymmetric synthesis of novel polyhydroxylated derivatives of indolizidine and quinolizidine by intramolecular 1,3-dipolar cycloaddition of N-(3-alkenyl)nitrones

  摘要：

  3-O-苄基-1,2-O-异亚丙基-1,5-戊二烯并-α-D-氧基呋喃糖与 N-（1,1-二甲基丁-3-烯基）羟基胺反应，然后进行分子内 1,3-二极环加成，得到 7-氧杂-1-氮杂双环[2.2.1]庚烷衍生物 4，很容易将其转化为新型多羟基喹嗪 6 和吲嗪 8。

  DOI：

  10.1039/b101057n

文献信息

• Preparation of highly substituted 7-oxa-1-azabicyclo[2.2.1]heptanes from 4-nitro-1-butene derivatives. Route to polysubstituted piperidines
  作者：Anna Budzińska、Wojciech Sas

  DOI：10.1016/s0040-4020(01)00021-7

  日期：2001.3

  4-Nitro-1-butene derivatives 2 readily available from the palladium(0)-catalyzed C-allylation of nitroalkanes were converted into highly substituted 7-oxa-1-azabicyclo[2.2.1]heptane derivatives 6 in three steps including an intramolecular 1,3-dipolar cycloaddition reaction. Catalytic hydrogenolysis of the N–O bond in 6 afforded polysubstituted 4-hydroxypiperidines.

  易于从钯（0）催化的硝基烷烃的C-烯丙基化反应中获得的4-硝基-1-丁烯衍生物2在包括分子内的三个步骤中转化为高度取代的7-氧杂-1-氮杂双环[2.2.1]庚烷衍生物6 1,3-偶极环加成反应。6中N–O键的催化氢解提供了多取代的4-羟基哌啶。
• Convenient synthesis of epimeric indolizidines by the intramolecular 1,3-dipolar cycloaddition of a sugar derived N-(3-alkenyl)nitrone
  作者：Ewa Mironiuk-Puchalska、Tomasz Rowicki、Wojciech Sas、Mariola Koszytkowska-Stawińska

  DOI：10.1016/j.tet.2013.09.008

  日期：2013.11

  The stereoselective synthesis of two epimeric penta-hydroxylated indolizidines was accomplished from 2,3:5,6-di-O-isopropylidene-α-d-mannofuranose and N-(2-methylpent-4-en-2-yl)hydroxylamine. The transformation of these substrates into the corresponding 7-oxa-1-azabicyclo[2.2.1]heptane by the intramolecular 1,3-dipolar cycloaddition was the key step of the synthesis. The adduct was transformed into

  2差向异构五羟基化indolizidines的立体选择性合成是由2,3-完成：5,6-二- ö异亚丙基α- d -mannofuranose和ñ - （2-甲基戊-4-烯-2-基）羟胺。这些底物转化成相应的7-氧杂- 1-氮杂双环[2.2.1]庚烷通过分子内1,3-偶极环加成化合物是合成的关键步骤。该加合物转化到通过分子内N-烷基化三环铵盐。通过以下方法将三环铵盐转化为目标化合物：（路线1）催化加氢；或（路线2）与叠氮化钠反应，然后通过对映选择性还原所得indolizidinone的。
• Arylboronic Acid-Catalyzed <i>C</i>-Allylation of Unprotected Oximes: Total Synthesis of <i>N</i>-Me-Euphococcine
  作者：Juha H. Siitonen、Padmanabha V. Kattamuri、Muhammed Yousufuddin、László Kürti

  DOI：10.1021/acs.orglett.0c00727

  日期：2020.3.20

  O-Unprotected keto- and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-alpha-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.
• Preparation of 2,2,6-trisubstituted 7-oxa-1-azabicyclo[2.2.1]heptanes from 4-nitro-1-butene derivatives. A route to 2,2,6-trisubstituted-4-hydroxypiperidines
  作者：Anna Budzińska、Maria Bukowska、Wojciech Sas

  DOI：10.1016/s0040-4039(98)02357-0

  日期：1999.1

  4-Nitro-1-butene derivatives 2 readily available from the palladium(0)-catalyzed C-allylation of nitroalkanes were converted into 7-oxa-1-azabicyclo[2.2.1]heptane derivatives 5 in three easy steps including an intramolecular 1,3-dipolar cycloaddition reaction of N-(3-alkenyl)nitrones. The palladium catalyzed hydrogenolysis of the compounds 5 afforded 2,2,6-trisubstituted-4-hydroxypiperidines The oxidation of 5 by 3 equiv. of m-chloroperbenzoic acid (MCPBA) gave acyclic beta-hydroxy-delta-nitroketones 9 in high yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of novel polyhydroxylated derivatives of indolizidine and quinolizidine by intramolecular 1,3-dipolar cycloaddition of N-(3-alkenyl)nitrones
  作者：Piotr Gębarowski、Wojciech Sas

  DOI：10.1039/b101057n

  日期：——

  Reaction of 3-O-benzyl-1,2-O-isopropylidene-1,5-pentadialdo-α- D-xylofuranose with N-(1,1-dimethylbut-3-enyl)hydroxylamine followed by intramolecular 1,3-dipolar cycloaddition yields 7-oxa-1-azabicyclo[2.2.1]heptane derivative 4, which is easily converted into novel polyhydroxylated quinolizidine 6 and indolizidine 8.

  3-O-苄基-1,2-O-异亚丙基-1,5-戊二烯并-α-D-氧基呋喃糖与 N-（1,1-二甲基丁-3-烯基）羟基胺反应，然后进行分子内 1,3-二极环加成，得到 7-氧杂-1-氮杂双环[2.2.1]庚烷衍生物 4，很容易将其转化为新型多羟基喹嗪 6 和吲嗪 8。