(S)-4-isopropyl-3-(4-methoxyphenyl)-4,5-dihydro-1,2,5-thiadiazoline-1,1-dioxide | 1421479-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-4-isopropyl-3-(4-methoxyphenyl)-4,5-dihydro-1,2,5-thiadiazoline-1,1-dioxide
• 英文别名: (3S)-4-(4-methoxyphenyl)-3-propan-2-yl-2,3-dihydro-1,2,5-thiadiazole 1,1-dioxide
• CAS: 1421479-21-1
• 化学式: C₁₂H₁₆N₂O₃S
• 分子量: 268.337
• InChiKey: BEDXKKXNUNBAOB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-isopropyl-3-(4-methoxyphenyl)-4,5-dihydro-1,2,5-thiadiazoline-1,1-dioxide 在 ruthenium trichloride 、 sodium periodate 、 锂硼氢 、 一水合肼 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 81.0h， 生成 (2R,3S)-4-methyl-2,3-bis(trifluoroacetamido)pentanoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of 3,4-Disubstituted cis- and trans-1,2,5-Thiadiazolidine-1,1-dioxides as Precursors for Chiral 1,2-Diamines

  摘要：

  Both, cis- and trans-3,4-disubstituted thiadiazolidines 5 and 6 can enantioselectively be obtained from thiadiazoles 2 which, in turn, are efficiently prepared from the respective 1,2-diketone by an improved protocol. An asymmetric ruthenium-catalyzed transfer hydrogenation followed by a diastereoselective hydride addition furnishes exclusively the cis-isomers 5 which, under acidic conditions, undergo a novel isomerization into the trans-isomers 6. These cyclic sulfamides can be transformed into 1,2-diamines as well as 2,3-diamino acids.

  DOI：

  10.1021/ol3034753
• 作为产物：
  描述：

  4-isopropyl-3-(4-methoxyphenyl)-1,2,5-thiadiazole-1,1-dioxide 在 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 甲酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以94%的产率得到(S)-4-isopropyl-3-(4-methoxyphenyl)-4,5-dihydro-1,2,5-thiadiazoline-1,1-dioxide
  参考文献：
  名称：

  Enantioselective Synthesis of 3,4-Disubstituted cis- and trans-1,2,5-Thiadiazolidine-1,1-dioxides as Precursors for Chiral 1,2-Diamines

  摘要：

  Both, cis- and trans-3,4-disubstituted thiadiazolidines 5 and 6 can enantioselectively be obtained from thiadiazoles 2 which, in turn, are efficiently prepared from the respective 1,2-diketone by an improved protocol. An asymmetric ruthenium-catalyzed transfer hydrogenation followed by a diastereoselective hydride addition furnishes exclusively the cis-isomers 5 which, under acidic conditions, undergo a novel isomerization into the trans-isomers 6. These cyclic sulfamides can be transformed into 1,2-diamines as well as 2,3-diamino acids.

  DOI：

  10.1021/ol3034753

文献信息

• Enantioselective Synthesis of 3,4-Disubstituted <i>cis</i>- and <i>trans</i>-1,2,5-Thiadiazolidine-1,1-dioxides as Precursors for Chiral 1,2-Diamines
  作者：Christian Schüttler、Zhen Li-Böhmer、Klaus Harms、Paultheo von Zezschwitz

  DOI：10.1021/ol3034753

  日期：2013.2.15

  Both, cis- and trans-3,4-disubstituted thiadiazolidines 5 and 6 can enantioselectively be obtained from thiadiazoles 2 which, in turn, are efficiently prepared from the respective 1,2-diketone by an improved protocol. An asymmetric ruthenium-catalyzed transfer hydrogenation followed by a diastereoselective hydride addition furnishes exclusively the cis-isomers 5 which, under acidic conditions, undergo a novel isomerization into the trans-isomers 6. These cyclic sulfamides can be transformed into 1,2-diamines as well as 2,3-diamino acids.