N,N'-dicyclopentylthiourea | 160712-65-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫脲类
• 英文名称: N,N'-dicyclopentylthiourea
• 英文别名: 1,3-Dicyclopentylthiourea
• CAS: 160712-65-2
• 化学式: C₁₁H₂₀N₂S
• 分子量: 212.359
• InChiKey: OVUIGZKRQUDDHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N'-dicyclopentylthiourea 在 甘氨酸乙酯盐酸盐 、 magnesium sulfate 、 三乙胺 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  Orlowska, A.; Izdebski, J., Polish Journal of Chemistry, 1994, vol. 68, # 4, p. 713 - 718

  摘要：

  DOI：
• 作为产物：
  描述：

  二硫化碳 、 环戊胺 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以69%的产率得到N,N'-dicyclopentylthiourea
  参考文献：
  名称：

  Orlowska, A.; Izdebski, J., Polish Journal of Chemistry, 1994, vol. 68, # 4, p. 713 - 718

  摘要：

  DOI：

文献信息

• Catalytic Enantioselective Biltz Synthesis
  作者：Di Tian、Zhuo‐Chen Li、Ze‐Hua Sun、Yu‐Ping He、Li‐Ping Xu、Hua Wu

  DOI：10.1002/anie.202313797

  日期：2023.11.27

  The first catalytic enantioselective Biltz synthesis is established, which provides a straightforward access to 5,5-disubstituted (thio)hydantoins in high yields with excellent stereocontrol. Isotopic tracer experiments and DFT calculations reveal an exclusive 1,2-ester shift process. The observed enantioselectivity and regioselectivity originate from [3+2] cyclization step.

  建立了第一个催化对映选择性 Biltz 合成法，它提供了一种直接获得高产率和出色立体控制的 5,5-二取代（硫代）乙内酰脲的方法。同位素示踪实验和 DFT 计算揭示了独特的 1,2-酯转移过程。观察到的对映选择性和区域选择性源自[3+2]环化步骤。
• Synthesis of Thioureas, Thioamides, and Aza-Heterocycles via Dimethyl-Sulfoxide-Promoted Oxidative Condensation of Sulfur, Malonic Acids, and Amines
  作者：Trung Hieu Do、Supasorn Phaenok、Darunee Soorukram、Tina Modjinou、Daniel Grande、Thi Thanh Tam Nguyen、Thanh Binh Nguyen

  DOI：10.1021/acs.orglett.3c02247

  日期：2023.9.1

  Malonic acid and derivatives have been well-known to undergo monodecarboxylation under relatively mild conditions and have been exclusively used as a C2 synthon. We report herein their new application as a C1 synthon via double decarboxylation promoted by sulfur and dimethyl sulfoxide. In the presence of amines as nucleophiles, a wide range of thioureas and thioamides as well as N-heterocycles were

  众所周知，丙二酸及其衍生物在相对温和的条件下进行单脱羧，并专门用作C 2合成子。我们在此报道了它们作为 C 1合成子的新应用，通过硫和二甲亚砜促进的双脱羧作用。在胺作为亲核试剂存在的情况下，在温和的加热条件下，可以以良好至优异的产率获得各种硫脲和硫代酰胺以及N-杂环。
• Sulfur‐ and Amine‐ Promoted Multielectron Autoredox Transformation of Nitromethane: Multicomponent Access to Thiourea Derivatives
  作者：Supasorn Phaenok、Le Anh Nguyen、Darunee Soorukram、Thi Thanh Tam Nguyen、Pascal Retailleau、Thanh Binh Nguyen

  DOI：10.1002/chem.202303703

  日期：2024.2

  Thiourea derivatives are in‐demand motifs in organic synthesis, medicinal chemistry and material science, yet redox methods for the synthesis that start from safe, simple, inexpensive and readily available feedstocks are scarce. In this article, we disclose the synthesis of these motifs using elemental sulfur and nitromethane as the starting materials. The method harnesses the multi‐electron auto‐redox property of nitromethane in the presence of sulfur and amines, delivering thiourea products without any added oxidant or reductant. Extension of this reaction to cyclizable amines and/or higher homologues of nitromethane led to a wide range of nitrogen heterocycles and thioamides. Operationally simple, the reactions are scalable, tolerate a wide range of functional groups, and can be employed for the direct functionalization of natural products. Mechanistically, the nitro group was found to act as an oxidant leaving group, being reduced to ammonia whereas sulfur, along with the role of a sulfur building block for the thiocarbonyl group, behaved as a complementary reductant, being oxidized to sulfate.

  摘要 硫脲衍生物是有机合成、药物化学和材料科学中炙手可热的基团，然而以安全、简单、廉价和易于获得的原料为起始原料的氧化还原合成方法却十分稀缺。本文披露了以元素硫和硝基甲烷为起始原料合成这些基团的方法。该方法利用了硝基甲烷在硫和胺存在下的多电子自动氧化还原特性，在不添加任何氧化剂或还原剂的情况下生成硫脲产品。将这一反应扩展到可环化胺和/或硝基甲烷的更高同系物，可得到多种氮杂环和硫代酰胺。该反应操作简单，可扩展性强，可容忍多种官能团，可用于天然产物的直接官能化。从机理上讲，硝基可作为氧化剂离去基团，被还原成氨，而硫作为硫代羰基的硫构件，可作为互补还原剂，被氧化成硫酸盐。
• Orally Bioavailable Isothioureas Block Function of the Chemokine Receptor CXCR4 In Vitro and In Vivo
  作者：Gebhard Thoma、Markus B. Streiff、Jiri Kovarik、Fraser Glickman、Trixie Wagner、Christian Beerli、Hans-Günter Zerwes

  DOI：10.1021/jm801065q

  日期：2008.12.25

  The interaction of the chemokine receptor CXCR4 with its ligand CXCL12 is involved in many biological processes such as hematopoesis, migration of immune cells, as well as in cancer metastasis. CXCR4 also mediates the infection of T-cells with X4-tropic HIV functioning as a coreceptor for the viral envelope protein gp120. Here, we describe highly potent, selective CXCR4 inhibitors that block CXCR4/CXCL12 interactions in vitro and in vivo Lis well as the infection of target cells by X4-tropic HIV.
• Orlowska, A.; Izdebski, J., Polish Journal of Chemistry, 1994, vol. 68, # 4, p. 713 - 718
  作者：Orlowska, A.、Izdebski, J.

  DOI：——

  日期：——