benzyl(2-nitro-1-phenylethyl)sulfane | 63509-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl(2-nitro-1-phenylethyl)sulfane
• 英文别名: 1-Phenyl-1-benzylmercapto-2-nitroethan；benzyl (2-nitro-1-phenylethyl) sulfide；Benzyl-(2-nitro-1-phenyl-aethyl)-sulfid；(1-Benzylsulfanyl-2-nitroethyl)benzene；(2-nitro-1-phenylethyl)sulfanylmethylbenzene
• CAS: 63509-11-5
• 化学式: C₁₅H₁₅NO₂S
• 分子量: 273.356
• InChiKey: DIVMEDXFGPUCAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 0.1h， 生成 benzyl(2-nitro-1-phenylethyl)sulfane
  参考文献：
  名称：

  An expeditious, highly efficient, catalyst-free and solvent-free synthesis of nitroamines and nitrosulfides by Michael addition

  摘要：

  一种简单、原子经济、高效且快速的绿色方法已被开发，用于通过简单混合或研磨，将胺和硫醇与硝基烯烃进行迈克尔加成，从而合成硝基胺和硝基硫化物。这种无催化剂和无溶剂的绿色方法在室温下能够在几分钟内定量产出加成产物。该方法不需要任何水淬火、溶剂分离和重结晶、柱色谱等纯化步骤。

  DOI：

  10.1039/c0gc00830c

文献信息

• [bmim]OH-promoted one-pot, three-component synthesis of β-nitro sulfides in water
  作者：Barahman Movassagh

  DOI：10.1080/10426507.2016.1146272

  日期：2016.8.2

  GRAPHICAL ABSTRACT ABSTRACT A task-specific ionic liquid, [bmim]OH, has been found to be a highly efficient catalyst for one-pot, three-component coupling of aryl aldehydes, nitromethane, and thiols for the synthesis of β-nitro sulfides in water. The main advantages of the present protocol include the use of inexpensive simple substrates and an ionic liquid as a basic catalyst.

  图形摘要摘要 一种特定任务的离子液体 [bmim]OH 已被发现是一种高效催化剂，可用于芳醛、硝基甲烷和硫醇的单锅三组分偶联，用于合成 β-硝基硫化物水。本协议的主要优点包括使用廉价的简单基材和离子液体作为基本催化剂。
• Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide
  作者：Cheng-Ming Chu、Zhijay Tu、Pohsi Wu、Chieh-Chieh Wang、Ju-Tsung Liu、Chun-Wei Kuo、Yu-Hsuan Shin、Ching-Fa Yao

  DOI：10.1016/j.tet.2009.02.074

  日期：2009.5

  Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.

  在无催化剂的反应条件下，溶剂介导的硫醇2加到β-硝基苯乙烯1中进行区域选择性控制，以良好或极好的收率得到加合物3或乙烯基硫化物4。为了使形成的产物合理化，提出了热力学和自催化反应机理。
• The Preparation of Some Aryl Aminoalkyl Sulfides and Sulfones^1,2
  作者：Louis F. Cason、Calvin C. Wanser

  DOI：10.1021/ja01145a051

  日期：1951.1
• β-Nitrosulfides and β-Aminosulfides
  作者：William E. Parham、Floyd L. Ramp

  DOI：10.1021/ja01147a125

  日期：1951.3
• An expeditious, highly efficient, catalyst-free and solvent-free synthesis of nitroamines and nitrosulfides by Michael addition
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1039/c0gc00830c

  日期：——

  A simple, atom economical, fast and highly efficient green protocol has been developed for the synthesis of nitroamines and nitrosulfides by the Michael addition of amines and thiols to nitroolefins by simple mixing or grinding. This catalyst-free and solvent-free green approach provided the addition products in quantitative yield within minutes at room temperature. This procedure does not require any water quenches, solvent separations and purification steps such as recrystallization and column chromatography.

  一种简单、原子经济、高效且快速的绿色方法已被开发，用于通过简单混合或研磨，将胺和硫醇与硝基烯烃进行迈克尔加成，从而合成硝基胺和硝基硫化物。这种无催化剂和无溶剂的绿色方法在室温下能够在几分钟内定量产出加成产物。该方法不需要任何水淬火、溶剂分离和重结晶、柱色谱等纯化步骤。