1-benzyl-5-fluoro-3-isothiocyanato-3H-indol-2-one | 1450988-92-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-benzyl-5-fluoro-3-isothiocyanato-3H-indol-2-one
• CAS: 1450988-92-7
• 化学式: C₁₆H₁₁FN₂OS
• 分子量: 298.341
• InChiKey: SMUOKOQJGSLRFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-fluoro-3-isothiocyanato-3H-indol-2-one 、 1-benzylidene-3-oxo-1-pyrazolidinium-2-ide 以 氯仿 为溶剂， 反应 0.08h， 以94%的产率得到1-benzyl-5-fluoro-4'-phenyl-1'-thioxo-1',2',6',7'-tetrahydrospiro[indoline-3,3'-pyrazolo[1,2-a][1,2,4]triazine]-2,8'(4'H)-dione
  参考文献：
  名称：

  Base-Catalyzed Diastereoselective [3 + 3] Annulation of 3-Isothiocyanatooxindoles and Azomethine Imines

  摘要：

  An unprecedented diastereoselective [3 + 3] annulation of 3-isothiocyanatooxindoles and azomethine imines was catalyzed by Et3N, affording 3,3'-triazinyl spirooxindoles in excellent yields and diastereoselectivities under mild conditions.

  DOI：

  10.1021/ol402295m

文献信息

• Facile construction of novel imidazolidine-spirooxindoles via diastereoselective cycloaddition of N-acylhydrazine-derived imines with 3-isothiocyanato oxindoles
  作者：Hong-Wu Zhao、Bo Li、Ting Tian、Xiu-Qing Song、Hai-Liang Pang、Xiao-Qin Chen、Zhao Yang、Wei Meng

  DOI：10.1039/c6ra01962e

  日期：——

  presence of 10 mol% of Na2CO3, the desired imidazolidine-spirooxindoles were obtained in 81–99% yield with up to 99 : 1 dr by means of the diastereoselective [3 + 2] cycloaddition of N-acylhydrazine-derived imines with 3-isothiocyanato oxindoles. Single-crystal X-ray structure analysis was conducted to determine the relative stereochemistry of the imidazolidine-spirooxindoles. Diastereoselective access

  在存在10 mol％的Na 2 CO 3时，通过衍生自N-酰基肼的非对映选择性[3 + 2]环加成反应，可以81-99％的收率获得所需的咪唑烷-螺氧并吲哚，最高可达99：1 dr。亚胺与3-异硫氰酸根合吲哚。进行了单晶X射线结构分析，以确定咪唑烷-螺氧还吲哚的相对立体化学。拟议的机制假设非对映选择性进入咪唑烷-spirooxindoles。
• Construction of spirothioureas having an amino quaternary stereogenic center <i>via</i> a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates
  作者：Hou-Ze Gui、Yin Wei、Min Shi

  DOI：10.1039/c8ob02748j

  日期：——

  useful and convenient strategy for the diastereoselective synthesis of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates was established. A diverse set of spirooxindole derivatives were synthesized in good to excellent yields and diastereoselectivities. Good enantioselectivities (up to 96 : 4 er) were obtained in

  通过3-异硫氰酸根合吲哚与2-氨基丙烯酸酯的[3 + 2]环化，建立了一个有用的方便的策略，用于非对映选择性合成具有氨基季立体中心的螺硫脲。合成了各种各样的螺氧杂吲哚衍生物，收率良好且具有非对映选择性。在随后的不对称研究中获得了良好的对映选择性（高达96：4 er）。
• Squaramide-Catalyzed Asymmetric Michael/Cyclization Cascade Reaction of Unsaturated Thiazolidinones and 3-Isothiocyanato Oxindoles: Synthesis of New Bispirocyclic Heterocycles
  作者：Da-Ming Du、Yong-Xing Song

  DOI：10.1055/s-0036-1591527

  日期：2018.4

  heterocycles bearing three contiguous chiral centers including two quaternary one via a Michael/cyclization cascade reaction has been developed. Using bifunctional cinchona-derived squaramide as catalyst, the reactions of 3-isothio­cyanato oxindoles with unsaturated thiazolidinone derivatives proceeded smoothly under mild reaction conditions to afford a series of complex chiral oxindole-pyrrolidone-thiazolidinone

  摘要 已开发出一种通过迈克尔/环化级联反应构建带有三个连续手性中心（包括两个四级手性中心）的羟吲哚-吡咯烷酮-噻唑烷酮双螺环杂环的高效方法。使用双功能金鸡纳衍生物方酸酰胺作为催化剂，3-异硫氰酸根合吲哚类化合物与不饱和噻唑烷酮衍生物的反应在温和的反应条件下平稳进行，从而提供了一系列复杂的手性羟吲哚-吡咯烷酮-噻唑烷酮双螺环杂环化合物，收率高（高达99％），且出色的非对映选择性和对映选择性（高达> 99：1 dr，> 99％ee）。 已开发出一种通过迈克尔/环化级联反应构建带有三个连续手性中心（包括两个四级手性中心）的羟吲哚-吡咯烷酮-噻唑烷酮双螺环杂环的高效方法。使用双功能金鸡纳衍生物方酸酰胺作为催化剂，3-异硫氰酸根合吲哚类化合物与不饱和噻唑烷酮衍生物的反应在温和的反应条件下平稳进行，从而提供了一系列复杂的手性羟吲哚-吡咯烷酮-噻唑烷酮双螺环杂环化合物，收率高（高达99％），且出色的非对映选择性和对映选择性（高达>
• Catalytic Asymmetric Michael Addition/Cyclization of Isothiocyanato Oxindoles: Highly Efficient and Versatile Approach for the Synthesis of 3,2′-Pyrrolidinyl Mono- and Bi-spirooxindole Frameworks
  作者：Yi-Ming Cao、Fang-Fang Shen、Fu-Ting Zhang、Rui Wang

  DOI：10.1002/chem.201204114

  日期：2013.1.21

  A‐spiro‐ing to greatness: The catalytic asymmetric Michael addition/cyclization of isothiocyanato oxindoles has been realized. This versatile approach provides an easy and highly efficient way to access not only the enantioselective synthesis of 3,2′‐pyrrolidinyl spirooxindole frameworks, but also the construction of enatiomerically enriched bi‐spirooxindoles containing three contiguous stereocenters

  令人叹为观止：已实现异硫氰酸根合吲哚的催化不对称迈克尔加成/环化反应。这种多用途的方法不仅提供了一种简便高效的方法，不仅可以访问3,2'-吡咯烷基吡啶螺吲哚骨架的对映选择性合成，还可以构建包含三个连续的立体中心和两个螺-季四中心的对映体富集的双螺并恶二醛（参见方案） ）。
• Construction of Novel Tetrahydro-<i>β</i>-carboline-1-thione Spirooxindoles by Brønsted Acid Mediated Formal [3+3] Cyclization of 3-Indolylmethanols with 3-Isothiocyanato Oxindoles
  作者：Yijun Liao、Mei Bai、Shuowen Yu、Minmin Zhang、Fangzhi Hu、Xiaoying Xu、Weicheng Yuan、Xiaomei Zhang

  DOI：10.1002/jhet.2708

  日期：2017.3

  p‐Toluenesulfonic acid mediated formal [3+3] cyclization of 3‐indolylmethanols with 3‐isothiocyanato oxindoles was realized. This transformation allowed for the synthesis of a series of novel tetrahydro‐β‐carboline‐1‐thione spirooxindoles in moderate to excellent yields (up to 99%) with generally good diastereoselectivities (up to >20:1). The structure of one product was determined by an X‐ray crystal

  对甲苯磺酸介导的3-异硫氰酸根合吲哚的3-吲哚基甲醇的正式[3 + 3]环化反应。这种转化可以合成一系列新型的四氢-β-咔啉-1-硫酮螺硫醇，其产率中等至优异（高达99％），非对映选择性良好（> 20：1）。一种产品的结构是通过X射线晶体结构分析确定的。