2-[N-(3-methylbut-2-enyl)-N-tosylamino]acetaldehyde | 1062368-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[N-(3-methylbut-2-enyl)-N-tosylamino]acetaldehyde
• 英文别名: 4-methyl-N-(3-methylbut-2-en-1-yl)-N-(2-oxoethyl)benzenesulfonamide；2-(N-prenyl-N-tosylamino)acetaldehyde；(N-(3-methylbut-2-enyl)-N-tosylamino) acetaldehyde；4-methyl-N-(3-methylbut-2-enyl)-N-(2-oxoethyl) benzenesulfonamide；4-methyl-N-(3-methylbut-2-enyl)-N-(2-oxoethyl)benzenesulfonamide
• CAS: 1062368-90-4
• 化学式: C₁₄H₁₉NO₃S
• 分子量: 281.376
• InChiKey: PWXDJTXGNUOWGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[N-(3-methylbut-2-enyl)-N-tosylamino]acetaldehyde 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 以1.29 g的产率得到2-[N-(3-methylbut-2-enyl)-N-tosylamino]acetaldehyde oxime
  参考文献：
  名称：

  Intramolecular Cycloaddition of O-tert-Butyldimethylsilyloximes in the Presence of BF₃·OEt₂

  摘要：

  Intramolecular cycloaddition of novel 1,3-dipoles, N-boranonitrones, was examined. Treatment of O-tert-butyldimethylsilyloximes 9-12 having olefin moieties with 2 equiv of BF3 center dot OEt2 generated N-boranonitrones, which underwent intramolecular cycloaddition to afford N-nonsubstituted cycloadducts 16 (and/or 18) after extractive workup. Despite the Lewis-acidic conditions, the olefin geometry of the substrates was retained in the cycloadducts in the present cycloaddition. The electronic nature of the N-boranonitrones appeared to be electrophilic. In the case of substrate 11c, having an electron-donating methyl group at an internal position of the olefin moiety, the cycloaddition gave the bridged cycloadduct 18b. The cycloaddition proceeded at relatively low temperature, and the diastereoselectivity was high.

  DOI：

  10.1021/jo051652e
• 作为产物：
  描述：

  1-氯-3-甲基-2-丁烯 在 二异丁基氢化铝 、 caesium carbonate 作用下， 以 乙醚 、 正己烷 、 丙酮 为溶剂， 反应 6.0h， 生成 2-[N-(3-methylbut-2-enyl)-N-tosylamino]acetaldehyde
  参考文献：
  名称：

  Intramolecular Cycloaddition of O-tert-Butyldimethylsilyloximes in the Presence of BF₃·OEt₂

  摘要：

  Intramolecular cycloaddition of novel 1,3-dipoles, N-boranonitrones, was examined. Treatment of O-tert-butyldimethylsilyloximes 9-12 having olefin moieties with 2 equiv of BF3 center dot OEt2 generated N-boranonitrones, which underwent intramolecular cycloaddition to afford N-nonsubstituted cycloadducts 16 (and/or 18) after extractive workup. Despite the Lewis-acidic conditions, the olefin geometry of the substrates was retained in the cycloadducts in the present cycloaddition. The electronic nature of the N-boranonitrones appeared to be electrophilic. In the case of substrate 11c, having an electron-donating methyl group at an internal position of the olefin moiety, the cycloaddition gave the bridged cycloadduct 18b. The cycloaddition proceeded at relatively low temperature, and the diastereoselectivity was high.

  DOI：

  10.1021/jo051652e

文献信息

• Thiocyanate radical mediated dehydration of aldoximes with visible light and air
  作者：Yong-Liang Ban、Jian-Ling Dai、Xiao-Ling Jin、Qing-Bao Zhang、Qiang Liu

  DOI：10.1039/c9cc05354a

  日期：——

  We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol

  我们开发了一种通过在室温下从硫氰酸铵和分子氧中原位生成的硫氰酸根来活化醛肟的新方法。用催化量的有机染料壬酸鸟嘌呤作为光催化剂，醛肟的脱水在可见光照射下平稳进行，提供了简单的操作，优异的官能团耐受性和适用于多种腈的无金属方案。
• A novel tandem ene/Prins cyclization for the synthesis of octahydropyrano[2,3-c]pyrrole derivatives
  作者：B.V. Subba Reddy、S. Rehana Anjum、G. Madhusudhan Reddy、J.S. Yadav

  DOI：10.1016/j.tetlet.2012.01.117

  日期：2012.4

  A tandem ene/Prins cyclization of olefin tethered aldehyde with an aldehyde has been accomplished using 5 mol % scandium triflate at ambient temperature to afford a novel series of cis-fused octahydropyrano[2,3-c]pyrrole derivatives in good yields with high selectivity. This is the first report on a tandem cyclization of 4-methyl-N-(3-methylbut-2-enyl)-N-(2-oxoethyl)benzenesulfonamide with aldehydes

  在环境温度下，使用5 mol％三氟甲磺酸accomplished，已完成了将烯烃与醛类连接的醛的串联烯烃/ Prins环化反应，从而以高收率和高选择性提供了一系列新型的顺式稠合八氢吡喃并[2,3- c ]吡咯衍生物。 。这是关于4-甲基-N-（3-甲基丁-2-烯基）-N-（2-氧乙基）苯磺酰胺与醛的串联环化的首次报道。
• Confined Acid-Catalyzed Asymmetric Carbonyl–Ene Cyclization
  作者：Luping Liu、Markus Leutzsch、Yiying Zheng、M. Wasim Alachraf、Walter Thiel、Benjamin List

  DOI：10.1021/jacs.5b09484

  日期：2015.10.21

  A highly enantioselective Brønsted acid catalyzed intramolecular carbonyl-ene reaction of olefinic aldehydes has been developed. Using a confined imidodiphosphate catalyst, the reaction delivers diverse trans-3,4-disubstituted carbo- and heterocyclic five-membered rings in high yields and with good to excellent diastereo- and enantioselectivities. ESI-MS, NMR, and DFT mechanistic studies reveal that

  已开发出高度对映选择性的布朗斯台德酸催化的烯醛分子内羰基-烯反应。使用受限的亚胺二磷酸盐催化剂，该反应以高产率和良好的非对映选择性和对映选择性提供了多种反式-3,4-二取代碳和杂环五元环。ESI-MS、NMR 和 DFT 机理研究表明，该反应通过涉及新型共价中间体的逐步途径进行。
• Stereodivergent Total Synthesis of Hapalindoles, Fischerindoles, Hapalonamide H, and Ambiguine H Alkaloids by Developing a Biomimetic, Redox-Neutral, Cascade Prins-Type Cyclization
  作者：Samrat Sahu、Beauty Das、Modhu Sudan Maji

  DOI：10.1021/acs.orglett.8b02804

  日期：2018.10.19

  redox-neutral, Brønsted acid-catalyzed cascade Prins-type cyclization between indole and aldehyde is described to access several structurally diverse indole terpenoid scaffolds in a single step. Applying this concept, stereodivergent total syntheses of nine hapalindole-type alkaloids are accomplished. Key transformations include allylation using geometrically isomeric allylboronic acid followed by a

  描述了在吲哚和醛之间的立体选择性，氧化还原中性，布朗斯台德酸催化的级联Prins型环化反应，可在一个步骤中进入多个结构多样的吲哚类萜骨架。应用该概念，完成了九种吲哚类生物碱的立体发散性总合成。关键的转化包括使用几何异构的烯丙基硼酸进行烯丙基化，然后使用对甲苯磺酸介导的脱保护-环化级联反应。
• A novel heterotricyclic assembly through intramolecular imino Diels–Alder reaction: synthesis of pyrrolo[3,4-b]quinolines
  作者：Mathesan Jayagobi、Mahalingam Poornachandran、Raghavachary Raghunathan

  DOI：10.1016/j.tetlet.2008.11.092

  日期：2009.2

  The synthesis of a series of hexahydropyrrolo[3,4-b]quinolines has been achieved in excellent yields by the reaction of aldimines derived from aromatic amines and N-prenylated aliphatic aldehydes in acetonitrile with InCl3 as a catalyst in a short duration of time.

  通过在短时间内以InCl 3为催化剂，衍生自芳族胺和N-异戊烯化脂肪醛的乙二胺在乙腈中以优异的产率合成了一系列六氢吡咯并[3,4- b ]喹啉。