2-benzylthio-Δ²-1,3-oxazoline | 120627-65-8

• 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-benzylthio-Δ²-1,3-oxazoline
• 英文别名: 2-Benzylsulfanyl-4,5-dihydro-1,3-oxazole
• CAS: 120627-65-8
• 化学式: C₁₀H₁₁NOS
• 分子量: 193.269
• InChiKey: NMLUTDRCELSONN-UHFFFAOYSA-N

物化性质

• 沸点：
  298.6±33.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzylthio-Δ²-1,3-oxazoline 在 溴甲苯 作用下， 反应 1.5h， 以40%的产率得到rac-3-benzyl-4-methoxycarbonyl-1,3-oxazolidine-2-thione
  参考文献：
  名称：

  Nagao, Yoshimitsu; Inoue, Keiko; Yamaki, Masae, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 11, p. 4293 - 4300

  摘要：

  DOI：
• 作为产物：
  描述：

  2-硫代四氢-1,3-恶唑 、 溴甲苯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以44%的产率得到2-benzylthio-Δ²-1,3-oxazoline
  参考文献：
  名称：

  Nagao, Yoshimitsu; Inoue, Keiko; Yamaki, Masae, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 11, p. 4293 - 4300

  摘要：

  DOI：

文献信息

• Benzylsulfanyloxazolines in Palladium-Catalyzed Cross-Coupling Reactions: A Novel Approach to Chiral Oxazolines
  作者：Arnaud Tatibouët、Franck Suzenet、Nicolas Leconte、Laurent Pellegatti、Patrick Rollin、Gerald Guillaumet

  DOI：10.1055/s-2007-965932

  日期：2007.3

  reaction with a range of organoboryl and organostannyl re- agents to produce 2-aryl- or 2-hetaryl-substituted oxazolines. Pro- tected and unprotected carbohydrate backbones were shown to be compatible with the reaction conditions. This approach opens a new versatile access to chiral oxazoline structures. The broad applicability of palladium-catalyzed carbon- carbon bond formation stems from the effectiveness

  合成了各种 2-苄基硫烷基-1,3-恶唑啉，并与一系列有机硼基和有机锡烷基试剂进行铜促进的钯催化交叉偶联反应，以产生 2-芳基或 2-杂芳基取代恶唑啉。受保护和未受保护的碳水化合物骨架显示出与反应条件相容。这种方法为手性恶唑啉结构开辟了新的通用途径。钯催化碳-碳键形成的广泛适用性源于该过程在中性介质中，在铃木、斯蒂尔或桧山反应中的有效性，这也是过去几年 Pd 交叉偶联出现的主要原因构建复杂分子的主要工具之一。1 在大多数这些反应中，亲电子伙伴是芳基或链烯基卤化物或磺酸盐，它们根据基材的性质显示出局限性，主要是由于制备困难或稳定性低。已经为克服这个问题做出了巨大的努力 2 并且最近，已经提出了杂芳基烷基硫化物作为一类新的电极。3 另一方面，1,3-恶唑烷-2-硫酮 (OZT) 是非芳族杂环，已在广泛的应用中使用。4 例如，这些简单的结构已被用于不对称 Diels-Alder 反应或其 N-取代衍生物的立体选择性烷基化。5
• Three-dimensional pharmacophore hypotheses of octopamine/tyramine agonists which inhibit [1-14C]acetate incorporation in Plodia interpunctella
  作者：Akinori Hirashima、Tomohiko Eiraku、Yoko Shigeta、Eiichi Kuwano

  DOI：10.1016/s0968-0896(02)00320-6

  日期：2003.1

  Three-dimensional pharmacophore hypotheses were built from a set of 36 octopamine (OA)/tyramine (TA) agonists responsible for the inhibition of sex-pheromone production in Plodia interpunctella. Among the ten chemical-featured models generated by a program Catalyst/Hypo, hypotheses including hydrogen-bond acceptor (HBA), hydrogen-bond acceptor aliphatic (HBAl), hydrophobic (Hp), hydrophobic aromatic (HpAr) and hydrophobic aliphatic (HpAl) features were considered to be important and predictive in evaluating OA/TA agonists. Active agonists mapped well onto all the features of the hypothesis such as HBA, HBAl, Hp, HpAr and HpAl features. On the other hand, inactive compounds were shown to be poorly capable of achieving an energetically favorable conformation shared by the active molecules in order to fit the 3-D chemical-feature pharmacophore models. Those hypotheses are considered to be used in designing new leads for hopefully more active compounds. Further research on the comparison of models from the agonists may help elucidate the mechanisms of OA/TA receptor-ligand interactions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A new and rapid access to homochiral 2,3-dihydro-oxazolo[2,3-b]quinazolin-5-ones
  作者：David Gueyrard、Onofrio Leoni、Sandro Palmieri、Patrick Rollin

  DOI：10.1016/s0957-4166(01)00032-5

  日期：2001.2

  Starting from homochiral 1,3-oxazolidine-2-thiones 1, a two-step sequence led to homotopic 2,3-dihydro-oxazolo[2,3-b]quinazolin-5-one derivatives 3. The sequence was developed and studied regarding its scope and limitations. (C) 2001 Elsevier Science Ltd. All rights reserved.
• NAGAO, YOSHIMITSU;INOUE, KEIKO;YAMAKI, MASAE;SHIRO, MOTOO;TAKAGI, SHUZO;F+, CHEM. AND PHARM. BULL., 36,(1988) N1, C. 4293-4300
  作者：NAGAO, YOSHIMITSU、INOUE, KEIKO、YAMAKI, MASAE、SHIRO, MOTOO、TAKAGI, SHUZO、F+

  DOI：——

  日期：——