(4R)-4-ethyl-1,3-oxazolidine-2-thione | 59170-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-4-ethyl-1,3-oxazolidine-2-thione
• 英文别名: (R)-4-ethyl-oxazolidine-2-thione；Sisaustricin
• CAS: 59170-06-8
• 化学式: C₅H₉NOS
• 分子量: 131.199
• InChiKey: IUQNMFMYZBLMEV-SCSAIBSYSA-N

物化性质

• 沸点：
  156.5±23.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-4-ethyl-1,3-oxazolidine-2-thione 在 sodium dihydrogenphosphate 、 sodium amalgam 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  N-Vinyl-1,3-oxazolidine-2-thiones as Dienophiles in Inverse Hetero-Diels-Alder Reactions: New Prospects for Asymmetric Induction

  摘要：

  几种 N-乙烯基-1,3-噁唑烷-2-硫酮（N-乙烯基 OZT）被方便地用作 Eu(fod)3 催化的涉及苯亚甲基丙酮酸甲酯的反向杂-Diels-Alder 反应中的新亲二烯烃。与相应的 N-乙烯基-1,3-噁唑烷-2-酮相比，简单的手性 N-乙烯基 OZT 类似物能均匀地获得中等的内向和外向非对映选择性。相比之下，从糖衍生的 N-乙烯基 OZT 具有较高的非对映选择性。

  DOI：

  10.1055/s-2006-939722
• 作为产物：
  描述：

  glucosisaustricin 在 phosphate buffer 、 Nylon 6,6-supported myrosinase 作用下， 生成 (4R)-4-ethyl-1,3-oxazolidine-2-thione
  参考文献：
  名称：

  Chemo-enzymatic preparation from renewable resources of enantiopure 1,3-oxazolidine-2-thiones

  摘要：

  Chiral 1,3-oxazolidine-2-thiones were prepared in enantiopure form from renewable resources through an enzymatic process involving immobilized myrosinase (thioglucoside glucohydrolase E.C. 3.2.3.1). (C) 2000 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0957-4166(99)00574-1

文献信息

• A New Method for the Synthesis of 5- and 6-Membered 2-Thioxo-1,3-O,N-heterocycles
  作者：Ge Li、Takahito Ohtani

  DOI：10.3987/com-97-7982

  日期：——

  Various 1,3-oxazolidine-2-thiones and tetrahydro-1,3-oxazine-2-thiones are prepared by reacting hydrogen peroxide with a mixture of amino alcohols, carbon disulfide and base in a water-miscible organic solvent. The yields of the heterocyclic products are in the range of 80 similar to 100%, considerably higher than those reported in literatures.
• Kjaer,A.; Christensen,B.W., Acta Chemica Scandinavica (1947), 1962, vol. 16, p. 71 - 77
  作者：Kjaer,A.、Christensen,B.W.

  DOI：——

  日期：——
• Nagao, Yoshimitsu; Kumagai, Toshio; Yamada, Shozo, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2361 - 2368
  作者：Nagao, Yoshimitsu、Kumagai, Toshio、Yamada, Shozo、Fujita, Eiichi、Inoue, Yoshinori、et al.

  DOI：——

  日期：——
• <i>N</i>-Vinyl-1,3-oxazolidine-2-thiones as Dienophiles in Inverse Hetero-Diels-Alder Reactions: New Prospects for Asymmetric Induction
  作者：Arnaud Tatibouët、Sébastien Tardy、Patrick Rollin、Gilles Dujardin

  DOI：10.1055/s-2006-939722

  日期：2006.6

  Several N-vinyl-1,3-oxazolidine-2-thione (N-vinyl OZT) were conveniently used as new dienophiles in Eu(fod)3-catalyzed reverse hetero-Diels-Alder reactions involving benzylidene pyruvic acid methyl ester. Simple chiral N-vinyl OZT analogues homogeneously led to moderate endo and facial diastereoselectivities, when compared to those obtained with the corresponding N-vinyl-1,3-oxazolidin-2-ones. In contrast, high diastereocontrols were ­observed with a sugar-derived N-vinyl OZT.

  几种 N-乙烯基-1,3-噁唑烷-2-硫酮（N-乙烯基 OZT）被方便地用作 Eu(fod)3 催化的涉及苯亚甲基丙酮酸甲酯的反向杂-Diels-Alder 反应中的新亲二烯烃。与相应的 N-乙烯基-1,3-噁唑烷-2-酮相比，简单的手性 N-乙烯基 OZT 类似物能均匀地获得中等的内向和外向非对映选择性。相比之下，从糖衍生的 N-乙烯基 OZT 具有较高的非对映选择性。
• Chemo-enzymatic preparation from renewable resources of enantiopure 1,3-oxazolidine-2-thiones
  作者：Onofrio Leoni、Roberta Bernardi、David Gueyrard、Patrick Rollin、Sandro Palmieri

  DOI：10.1016/s0957-4166(99)00574-1

  日期：1999.12

  Chiral 1,3-oxazolidine-2-thiones were prepared in enantiopure form from renewable resources through an enzymatic process involving immobilized myrosinase (thioglucoside glucohydrolase E.C. 3.2.3.1). (C) 2000 Elsevier Science Ltd. AII rights reserved.