(S)-N-allyl-N-(1-hydroxypropan-2-yl)-4-methylbenzenesulfonamide | 1296866-33-5

• 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: (S)-N-allyl-N-(1-hydroxypropan-2-yl)-4-methylbenzenesulfonamide
• 英文别名: N-[(2S)-1-hydroxypropan-2-yl]-4-methyl-N-prop-2-enylbenzenesulfonamide
• CAS: 1296866-33-5
• 化学式: C₁₃H₁₉NO₃S
• 分子量: 269.365
• InChiKey: XDXOYFIXIVHHBO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-N-allyl-N-(1-hydroxypropan-2-yl)-4-methylbenzenesulfonamide 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 硫代乙酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以60%的产率得到N-allyl-N-(1-mercaptopropan-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  通过N系硫代链烯醇的分子内环化， 高度区域选择性合成4- tosylthiomorpholine †

  摘要：

  已经开发了一种一锅无金属的方法，该方法可通过溴化，环化和随后的消除反应，以高收率从N系硫代链烯醇合成4-甲苯基硫代吗啉。发现该反应是高度区域选择性的。

  DOI：

  10.1039/c6ob01869f
• 作为产物：
  描述：

  methyl N-allyl-N-tosyl-L-alaninate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (S)-N-allyl-N-(1-hydroxypropan-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  I₂-Mediated Diversity Oriented Diastereoselective Synthesis of Amino Acid Derived trans-2,5-Disubstituted Morpholines, Piperazines, and Thiomorpholines

  摘要：

  Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents.

  DOI：

  10.1021/co200129t

文献信息

• Aryl λ³-Iodane-Mediated 6-<i>exo</i>-<i>trig</i>Cyclization to Synthesize Highly Substituted Chiral Morpholines
  作者：Jaya Kishore Vandavasi、Wan-Ping Hu、Gopal Chandru Senadi、Hui-Ting Chen、Hsing-Yin Chen、Kuang-Chan Hsieh、Jeh-Jeng Wang

  DOI：10.1002/adsc.201500177

  日期：2015.9.14

  A mild and efficient transition metal‐free approach has been developed for the synthesis of highly substituted chiral morpholines from alkenols by amino acid‐derived iodine(III) reagents via a 6‐exo‐trig cyclization. The key features of this work include the formation of three chiral centers with a high diastereomeric ratio, broad functional group compatibility, and atom/time economic methodology.

  已经开发了一种温和有效的无过渡金属的方法，用于通过氨基酸衍生的碘（III）试剂通过6- exo - trig环化反应从烯醇合成高度取代的手性吗啉。这项工作的关键特征包括形成具有高非对映异构体比率，广泛的官能团相容性和原子/时间经济方法的三个手性中心。
• Stereoselective Synthesis of Morpholines via Copper-Promoted Oxyamination of Alkenes
  作者：Fatima C. Sequeira、Sherry R. Chemler

  DOI：10.1021/ol301984b

  日期：2012.9.7

  A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines were synthesized in good to excellent yields and diastereoselectivities.

  报道了一种新的 2-乙基己酸铜 (II) 促进的醇和胺在烯烃上的加成（氧胺化）。醇加成是分子内的，而与胺的偶联发生在分子间。合成了几种 2-氨基甲基吗啉，收率和非对映选择性都非常好。
• Ni-catalyzed two-component reductive dicarbofunctionalization of alkenes <i>via</i> radical cyclization
  作者：Yulong Kuang、Xuefeng Wang、David Anthony、Tianning Diao

  DOI：10.1039/c8cc00358k

  日期：——

  A reductive dicarbofunctionalization reaction of alkenes has been developed and applied to the preparation of substituted carbo- and heterocycles. The reaction conditions avoid the use of air-sensitive organometallic reagents, and are compatible with a broad range of bromo-electrophiles and a wide variety of substituents to give cyclic products in excellent yields.

  已经开发了烯烃的还原性双碳官能化反应，并将其用于制备取代的碳环和杂环。反应条件避免了使用对空气敏感的有机金属试剂，并且可与各种溴亲电子试剂和各种取代基兼容，从而以优异的收率得到环状产物。
• Intramolecular Oxidative Pd(II)-Catalyzed Alkoxylation of 3-Aza-5-alkenols with O2 as Sole Oxidant: Mild Conditions for the Synthesis of 1,4-Oxazine Derivatives
  作者：Gianluigi Broggini、Egle Beccalli、Elena Borsini、Andrea Fasana、Gaetano Zecchi

  DOI：10.1055/s-0030-1259295

  日期：2011.1

  Synthesis of 1,4-2H-oxazine derivatives was performed by Pd(II)-catalyzed aerobic oxidative cyclization of 3-aza-5-al­kenols, prepared from easily available 1,2-amino alcohols. The ­reaction proceeds in very mild conditions with a simple catalytic system consisting of PdCl2(MeCN)2 in THF at room temperature with molecular oxygen as the sole stoichiometric oxidant.

  1,4-2H-吡嗪衍生物的合成是通过Pd(II)催化的有氧氧化环化反应实现的，该反应使用了由易得的1,2-氨基醇制备的3-氮-5-烯醇。在极温和的条件下，该反应在室温下以THF中的PdCl2(MeCN)2作为简单的催化系统，分子氧作为唯一的计量氧化剂进行。