(S)-N-allyl-N-(1-mercapto-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide | 1352166-29-0

• 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-mercapto-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide
• 英文别名: (S)-2-(allylamino)-3-phenylpropane-1-thiol
• CAS: 1352166-29-0
• 化学式: C₁₉H₂₃NO₂S₂
• 分子量: 361.529
• InChiKey: FMJAXDQFXHYCFN-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  37.38
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N-allyl-N-(1-mercapto-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (2S,5S)-5-benzyl-2-(iodomethyl)-4-tosylthiomorpholine
  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
• 作为产物：
  描述：

  methyl N-allyl-N-tosyl-L-phenylalaninate 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (S)-N-allyl-N-(1-mercapto-3-phenylpropan-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

• Catalyst free annulative thioboration of unfunctionalized olefins
  作者：Zhantao Yang、Chun-Hua Yang、Shiqi Chen、Xixi Chen、Litian Zhang、Huijun Ren

  DOI：10.1039/c7cc06800j

  日期：——

  BCl3 as the sole boron source, the boryl group and thiol group are added to the C-C double bonds simultaneously. After hydrolysis, the corresponding ((tetrahydrothiophen-2-yl)methyl)boronic acid, ((tetrahydro-2H-thiopyran-2-yl)methyl)boronic acid, ((2,3-dihydrobenzo[b]thiophen-2-yl)methyl)boronic acid and (thiomorpholin-2-ylmethyl)boronic acid are obtained with good yield. The boronic acids obtained

  已开发出未官能化烯烃的直接且无催化剂的环烷基硫代硼酸酯化反应。在BCl3作为唯一硼源的情况下，将硼烷基和硫醇基同时加到CC双键上。水解后，得到相应的（（四氢噻吩-2-基）甲基）硼酸，（（四氢-2H-硫代吡喃-2-基）甲基）硼酸，（（2,3-二氢苯并[b]噻吩-2-基以良好的产率获得了（甲基）硼酸和（硫代吗啉-2-基甲基）硼酸。可以保护所获得的硼酸以形成合成普遍存在的频哪醇硼酸酯。
• Highly regioselective synthesis of 4-tosylthiomorpholine via intramolecular cyclization of N-tethered thioalkenols
  作者：Anil K. Saikia、Manash J. Deka、Upasana Borthakur

  DOI：10.1039/c6ob01869f

  日期：——

  A one-pot, metal-free procedure has been developed for the synthesis of 4-tosylthiomorpholine from N-tethered thioalkenols via bromination, cyclization and subsequent elimination reaction in good yields. The reaction is found to be highly regioselective.

  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。