2,2-bis(propylthio)-5,5-dimethyl-Δ³-1,3,4-oxadiazoline | 222625-77-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2,2-bis(propylthio)-5,5-dimethyl-Δ³-1,3,4-oxadiazoline
• 英文别名: 2,2-Dimethyl-5,5-bis(propylthio)-1,3,4-oxadiazole；2,2-dimethyl-5,5-bis(propylsulfanyl)-1,3,4-oxadiazole
• CAS: 222625-77-6
• 化学式: C₁₀H₂₀N₂OS₂
• 分子量: 248.414
• InChiKey: FJYVPCVLZLZWFK-UHFFFAOYSA-N

物化性质

• 沸点：
  335.0±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-bis(propylthio)-5,5-dimethyl-Δ³-1,3,4-oxadiazoline 以 苯 为溶剂， 生成 1-[Bis(propylsulfanyl)methyl]-3,3,4,4-tetrakis(propylsulfanyl)-4a,5,6,7-tetrahydroquinolin-2-one
  参考文献：
  名称：

  合成中的亲核卡宾。[1 + 4]双（烷硫基）卡宾与乙烯基异氰酸酯的环加成反应。

  摘要：

  DOI：

  10.1021/jo9823801
• 作为产物：
  描述：

  N'-isopropylidene-hydrazinecarbothioic acid S-propyl ester 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2,2-bis(propylthio)-5,5-dimethyl-Δ³-1,3,4-oxadiazoline
  参考文献：
  名称：

  Bis(alkylthio)carbenes as Novel Reagents for Organic Synthesis

  摘要：

  Bis(alkylthio)carbenes have been shown to be a useful class of reactive intermediates for applications to organic synthesis. Substituted hydroindolanes, isatins and hydroquinolones can be prepared by the addition of these carbenes to vinyl isocyanates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00855-3

文献信息

• Total Synthesis of (±)-Phenserine <i>via</i> [4+1] Cyclization of a Bis(alkylthio)carbene and an Indole Isocyanate
  作者：James H. Rigby、Shyama Sidique

  DOI：10.1021/ol062915+

  日期：2007.3.1

  [structure: see text]. A total synthesis of acetylcholine blocking agent, phenserine, has been achieved by employing a [4+1] cyclization between an appropriately substituted indole isocyanate and a bis(alkylthio)carbene.

  [结构：见文字]。通过在适当取代的吲哚异氰酸酯和双（烷硫基）卡宾之间进行[4 + 1]环化反应，可以实现乙酰胆碱封闭剂酚丝氨酸的全合成。
• [4 + 1] Cycloaddition of Bis(alkylthio)carbenes with Vinyl Isocyanates. Total Synthesis of (±)-Mesembrine
  作者：James H. Rigby、Weitong Dong

  DOI：10.1021/ol005706c

  日期：2000.6.1

  [reaction: see text] The Sceletium alkaloid mesembrine has been synthesized in 13% overall yield by a sequence featuring a [4 + 1] cycloaddition of a bis(alkylthio)carbene with a functionalized vinyl isocyanate.

  [反应：见正文] Sceletium生物碱甲基苯丙氨酸甲酯已通过具有双（烷硫基）卡宾与官能化的异氰酸乙烯基酯的[4 +1]环加成的序列合成，总收率为13％。
• Synthesis of Highly Substituted Cyclopentenones via the [4 + 1] Cycloaddition of Nucleophilic Carbenes and Vinyl Ketenes
  作者：James H. Rigby、Zhengqiang Wang

  DOI：10.1021/ol0272141

  日期：2003.2.1

  [reaction: see text] Vinyl ketenes have been shown to undergo [4 + 1] cycloaddition with a variety of nucleophilic carbenes to deliver highly substituted cyclopentenones as products.

  [反应：见正文]已显示乙烯基烯酮与各种亲核碳烯发生[4 +1]环加成反应，以提供高度取代的环戊烯酮作为产物。
• Total synthesis of (±)-debromoflustramine B via [4+1] cyclization of a bis(alkylthio)carbene and an indole isocyanate
  作者：Saptarshi De、James H. Rigby

  DOI：10.1016/j.tetlet.2013.06.119

  日期：2013.8

  An efficient total synthesis of (±)-debromoflustramine B and (±)-debromoflustramide B has been achieved, through a novel [4+1] cyclization of an indole isocyanate and bis(alkylthio)carbene.

  通过吲哚异氰酸酯和双（烷硫基）卡宾的新型[4 + 1]环化，已实现了（±）-溴代去氟乙酰胺B和（±）-溴代去氟乙酰胺B的有效全合成。
• Rapid construction of isatin derivatives via addition of bis(alkylthio)carbenes to aryl isocyanates
  作者：James H. Rigby、M.Diana Danca

  DOI：10.1016/s0040-4039(99)01392-1

  日期：1999.9

  Thermally induced cyclization between bis(alkylthio)carbenes, derived from the corresponding oxadiazolines, and substituted aryl isocyanates provides access to a variety of isatin derivatives with good efficiency. (C) 1999 Elsevier Science Ltd. All rights reserved.