3-Prop-2-enylsulfanyl-1,3-dihydroindol-2-one | 1424194-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-Prop-2-enylsulfanyl-1,3-dihydroindol-2-one
• CAS: 1424194-05-7
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: GWDKEKDEUYWGQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-2-硝基乙烯 、 3-Prop-2-enylsulfanyl-1,3-dihydroindol-2-one 在 C₂₉H₄₄N₃O₃P 作用下， 以 乙醚 为溶剂， 反应 36.0h， 以91%的产率得到
  参考文献：
  名称：

  Highly enantioselective Michael addition of 3-arylthio- and 3-alkylthiooxindoles to nitroolefins catalyzed by a simple cinchona alkaloid derived phosphoramide

  摘要：

  一种新的来源于奎宁生物碱的双功能三级胺-磷酰胺C1e被鉴定为对未保护的3-芳基硫代和3-烷基硫代氧啶向硝基烯烃的迈克尔加成反应的高立体选择性催化剂。C1e的磷酰胺部分在该反应中发挥了不可或缺的作用。

  DOI：

  10.1039/c4cc06417h

文献信息

• PROCESS FOR THE PREPARATION OF OXINDOLES AND ORTHO-SUBSTITUTED ANILINES AND THEIR USE AS INTERMEDIATES FOR SYNTHESES
  申请人：Ford Mark James

  公开号：US20110118478A1

  公开（公告）日：2011-05-19

  The present invention relates to processes for the preparation of oxindoles and ortho-substituted anilines and their use as intermediates for syntheses. The invention further relates to a process for the preparation of compounds of formula (4): where a mixture of an aniline (compound of formula Q) is reacted with a thioether (compound of formula W): in the presence of a chlorinating agent and an organic solvent at a reaction temperature in the range above −65° C. In a subsequent process, this compound is further reacted in the presence of an acid catalyst to give the indole of formula (7) or the oxindole of formula (8):

  本发明涉及制备氧吲哚和邻位取代苯胺的过程，以及它们作为合成中间体的用途。该发明进一步涉及一种制备化合物的过程，该化合物的结构如下所示：其中苯胺（化合物Q的结构）的混合物与硫醚（化合物W的结构）在氯化剂和有机溶剂存在下在高于-65°C的反应温度下反应。在随后的过程中，该化合物在酸催化剂存在下进一步反应，得到下述吲哚（结构为7）或氧吲哚（结构为8）：
• Process for Preparing Substituted 1,3-dihydro-2H-indol-2-ones
  申请人：Siegel Konrad

  公开号：US20110275832A1

  公开（公告）日：2011-11-10

  Process for preparing 1,3-dihydro-2H-indol-2-ones, starting from thioalkyl-, or thiocycloalkyl-substituted indol-2-one compounds, involving a) dissolving or suspending the thioalkyl-, or thiocycloalkyl-substituted indol-2-one compounds in a polar solvent, b) adding a sulfur-containing salt to the solution or suspension, and c) heating the reaction mixture under reflux at a temperature which corresponds at most to the boiling temperature of the solvent. Use of the inventively prepared 1,3-dihydro-2H-indol-2-one as intermediates for the synthesis of fine chemicals and active ingredients from pharmacy and/or agriculture.

  从含有硫代烷基或硫代环烷基取代的吲哚-2-酮化合物开始，制备1,3-二氢-2H-吲哚-2-酮的过程，涉及a)将含有硫代烷基或硫代环烷基取代的吲哚-2-酮化合物溶解或悬浮在极性溶剂中，b)向溶液或悬浮液中加入含硫盐，以及c)在回流下加热反应混合物，温度最高不超过溶剂的沸点温度。利用创造性制备的1,3-二氢-2H-吲哚-2-酮作为合成精细化学品和药学和/或农业活性成分的中间体。
• Catalytic asymmetric sulfenylation to structurally diverse dithioketals
  作者：Kui Liao、Feng Zhou、Jin-Sheng Yu、Wei-Ming Gao、Jian Zhou

  DOI：10.1039/c5cc07010d

  日期：——

  We report the first example of highly enantioselective synthesis of structurally diverse chiral dithioketalsviaasymmetric sulfenylation of various types of S-based nucleophiles, catalyzed by a cheap cinchona alkaloid derivative, dihydroquinine.

  我们报告了通过对各种类型的基于硫的亲核试剂进行不对称砜化反应，由廉价的奎宁生物碱衍生物二氢奎宁催化合成结构多样手性二硫醚的高对映选择性合成的首个示例。
• Organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at the C3 position
  作者：Feng Zhou、Xing-Ping Zeng、Chao Wang、Xiao-Li Zhao、Jian Zhou

  DOI：10.1039/c3cc38819k

  日期：——

  We report the first organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at the C3 position. Importantly, 3-thiooxindoles and 3-alkoxyoxindoles are demonstrated to be reactive nucleophiles for the development of catalytic asymmetric reactions for the first time.

  我们报道了首次使用有机催化方法进行的不对称合成3,3-二取代氧杂吲哚，该氧杂吲哚在C3位置具有两个杂原子。重要的是，首次证明了3-硫氧杂吲哚和3-烷氧氧杂吲哚可以作为反应性亲核试剂用于发展催化不对称反应。
• METHOD FOR PRODUCING TRIAZINYL-SUBSTITUTED OXINDOLES
  申请人：Karig Gunter

  公开号：US20130345422A1

  公开（公告）日：2013-12-26

  Process for the preparation of triazinyl-substituted oxindoles of formula (3) and salts thereof by reacting an oxindole (1) with a triazine (2) in the presence of a carbonate, a hydroxide, a phosphate or a mixture of two or more of the aforementioned compounds, and also the compounds of formula (3) and salts thereof (3″) and the use of both for producing crop protection agents.

  通过在碳酸盐、氢氧化物、磷酸盐或两种或两种以上上述化合物的混合物存在下，将氧吲哚(1)与三嗪(2)反应，制备式(3)的三嗪基取代的氧吲哚及其盐(3″)，并将两者用于生产农作物保护剂的方法。