2-((1S,2S)-2-isothiocyanatocyclohexyl)isoindoline-1,3-dione | 1426836-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((1S,2S)-2-isothiocyanatocyclohexyl)isoindoline-1,3-dione
• CAS: 1426836-08-9
• 化学式: C₁₅H₁₄N₂O₂S
• 分子量: 286.354
• InChiKey: DPHZPQNVFBEKFM-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.74
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((1S,2S)-2-isothiocyanatocyclohexyl)isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.5h， 生成 1-(3-(4-tert-butylphenoxy)propyl)-3-((1S,2S)-2-(diethylamino)cyclohexyl)thiourea
  参考文献：
  名称：

  Novel efficient bifunctional calixarene thiourea organocatalysts: synthesis and application in the direct enantioselective aldol reactions

  摘要：

  Novel efficient bifunctional calixarene thiourea organocatalysts have been designed as efficient organocatalysts for direct asymmetric aldol reactions between acetone and aromatic aldehydes. The reactions generated the corresponding products in satisfactory isolated yields (up to 96%) and with excellent enantiomeric excesses (up to 99%) in the presence of catalyst (10 mol %). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.01.011
• 作为产物：
  描述：

  (1S,2S)-N-phthaloyl-1,2-diaminocyclohexane 、 硫光气 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-((1S,2S)-2-isothiocyanatocyclohexyl)isoindoline-1,3-dione
  参考文献：
  名称：

  伯胺硫脲有机催化剂催化的硝基化合物对硝基烯烃的高对映选择性迈克尔加成反应

  摘要：

  一系列伯胺硫脲双功能催化剂具有高对映选择性（90-98％ee）和优异的收率（80-96％），已成功地引发了醛与硝基烯烃的迈克尔不对称迈克尔加成反应。发现特权的奎宁支架对于反应效率和对映选择性是必不可少的。

  DOI：

  10.1016/j.tet.2010.05.056

文献信息

• Novel and highly efficient bifunctional calixarene thiourea derivatives as organocatalysts for enantioselective Michael reaction of nitroolefins with diketones
  作者：Hayriye Nevin Genc、Abdulkadir Sirit

  DOI：10.1007/s10847-017-0761-1

  日期：2018.2

  New bifunctional calixarene thiourea organocatalysts were synthesized and applied in catalytic asymmetric Michael addition of acetylacetone to various nitroolefins at room temperature. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 92% ee). The present research demonstrates the advantages of incorporating two stereocontrolling structures

  合成了新的双功能杯芳烃硫脲有机催化剂，并应用于室温下乙酰丙酮与各种硝基烯烃的催化不对称迈克尔加成反应。相应的加合物以良好到极好的收率获得，具有极好的对映选择性（高达 92% ee）。本研究证明了将两种立体控制结构结合到单一催化剂中的优势。值得注意的是，它为手性有机分子的催化不对称合成提供了一种简单方便的双立体控制方法。
• Calixarene-based highly efficient primary amine–thiourea organocatalysts for asymmetric Michael addition of aldehydes to nitrostyrenes
  作者：Mustafa Durmaz、Abdulkadir Sirit

  DOI：10.1080/10610278.2013.773331

  日期：2013.5.1

  The synthesis of calix[4]arene-based chiral bifunctional primary amine–thiourea catalysts has been described from p-tert-butylcalix[4]arene for the first time. The calix[4]arene-based catalysts were successfully applied to promote Michael addition of aldehydes with nitroalkenes affording preferentially the (R)- or (S)-adducts in high yields (up to 95%) and excellent enantioselectivities (up to 99%

  首次描述了从对叔丁基杯[4]芳烃合成基于杯[4]芳烃的手性双功能伯胺-硫脲催化剂。杯[4]芳烃基催化剂被成功应用于促进醛与硝基烯烃的迈克尔加成，优先提供（R）-或（S）-加合物的高产率（高达95%）和优异的对映选择性（高达99%） es）。
• Primary amine–thiourea grafted graphene–based heterogeneous chiral catalysts for highly enantioselective Michael additions
  作者：Sayed Mustafa Badr、Manel Azlouk、Erhan Zor、Haluk Bingol、Mustafa Durmaz

  DOI：10.1016/j.mcat.2022.112383

  日期：2022.6

  coupling reaction. The surface modification of GO was analyzed by a combination of Fourier-transform infrared spectroscopy (FT-IR), Raman spectroscopy, X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM) and transmission electron spectroscopy (TEM) techniques. The catalytic performances of graphene-based materials were investigated in the asymmetric Michael addition reactions of α

  基于地球丰富的碳材料的多相不对称催化结合了固体催化剂易于分离、再生简单和高稳定性等优点，是金属基催化剂的低成本、环保无金属替代品. 两种新型双功能碳催化剂 [ (S,S)和(R,R) GO-PATU] 是通过硅烷偶联反应将带有伯胺和硫脲基团的对映体纯有机硅烷共价固定在氧化石墨烯 (GO) 骨架上而制备的。通过结合傅里叶变换红外光谱 (FT-IR)、拉曼光谱、X 射线光电子能谱 (XPS)、扫描电子显微镜 (SEM) 和透射电子能谱 (TEM) 技术分析 GO 的表面改性。研究了石墨烯基材料在α,α-二取代醛与硝基苯乙烯和N的不对称迈克尔加成反应中的催化性能-取代的马来酰亚胺。使用两种催化剂评估溶剂和布朗斯台德碱性或酸性添加剂的影响，在室温下，在l-和d-樟脑磺酸存在下，在二氯甲烷中获得了良好的收率（高达 85%）和立体选择性（高达 95% ee）酸。此外，还成功地进行了催化剂的回收和再利用研究。
• Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides
  作者：Mustafa Durmaz、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2013.09.010

  日期：2013.12

  Calix[4]arene based chiral bifunctional thiourea-primary amines have been shown to act as effective catalysts for the Michael addition of aldehydes to maleimides for the first time. The corresponding adducts were generally obtained preferentially in (R)- or (S)-forms with high yields (up to 99%) and with high to excellent enantioselectivities (up to 98% ee). (C) 2013 Elsevier Ltd. All rights reserved.
• Calixarene-derived chiral tertiary amine–thiourea organocatalyzed asymmetric Michael additions of acetyl acetone and dimethyl malonate to nitroolefins
  作者：Mustafa Durmaz、Aysun Tataroglu、Horu Yilmaz、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2016.01.004

  日期：2016.2

  Novel bifunctional chiral thiourea-tertiary amines bearing a calix[4]arene scaffold were synthesized and applied in catalytic asymmetric Michael addition of acetyl acetone and dimethyl malonate to nitroolefins. The corresponding adducts were obtained in excellent yields (up to 99%) and with high enantioselectivities (up to 94% ee). (C) 2016 Elsevier Ltd. All rights reserved.