(R)-(+)-3-(4-methoxyphenylsulfanyl)-1,3-diphenylpropan-1-one | 374620-29-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-(+)-3-(4-methoxyphenylsulfanyl)-1,3-diphenylpropan-1-one
• 英文别名: (R)-1,3-diphenyl-3-(p-methoxyphenylsulfanyl)-propan-1-one；(3R)-3-[(4-Methoxyphenyl)thio]-1,3-diphenyl-1-propanone；(3R)-3-(4-methoxyphenyl)sulfanyl-1,3-diphenylpropan-1-one
• CAS: 374620-29-8
• 化学式: C₂₂H₂₀O₂S
• 分子量: 348.466
• InChiKey: TWTFUSQOBVYYCG-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 反式-查耳酮 在 辛可宁 作用下， 以 甲苯 为溶剂， 生成 (R)-(+)-3-(4-methoxyphenylsulfanyl)-1,3-diphenylpropan-1-one 、 (S)-(-)-3-(4-methoxyphenylsulfanyl)-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: easily available new chiral building blocks

  摘要：

  A facile and enantioselective method for the multigram preparation of the title compounds is described. The Michael addition of thiophenols to chalcones catalyzed by (+)-cinchonine, followed by crystallization, led to the corresponding adducts 2 in up to > 95% e.e. The stereoselective Beckmann rearrangement of the oxime of (+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one 2a gives the anilide of (R)-(+)-3-phenyl-3-phenylsulfanylpropanoic acid (as determined by X-ray analysis) and alcoholysis leads to the corresponding enantiomerically pure ethyl ester. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00330-5

文献信息

• Investigating the efficacy of green solvents and solvent-free conditions in hydrogen-bonding mediated organocatalyzed model reactions
  作者：Lloyd C. Chetty、Hendrik G. Kruger、Per I. Arvidsson、Tricia Naicker、Thavendran Govender

  DOI：10.1039/d4ra00679h

  日期：——

  restricts its application to reactions that require non-polar solvents. Furthermore, pursuing solvent-free conditions, even without liquid substrates, might result in similar conversion rates with reduced catalyst loading. These findings highlight the potential of exploring solvent-free conditions when enantioselectivity is not of concern. Based on the results, solvent-free conditions and bio-based solvents

  在这项研究中，我们深入研究了使用绿色溶剂或无溶剂条件下进行的各种反应，利用氢键有机催化来推进化学合成中更可持续的实践。结果表明，环戊基甲基醚有可能取代己烷和甲苯等非极性有机溶剂，并具有相当的对映选择性和产率。液化或超临界CO 2的非极性性质限制了其在需要非极性溶剂的反应中的应用。此外，追求无溶剂条件，即使没有液体底物，也可能在减少催化剂负载的情况下产生相似的转化率。这些发现凸显了在不关心对映选择性时探索无溶剂条件的潜力。根据结果​​，无溶剂条件和生物基溶剂可以作为传统有机溶剂的可行替代品，而不会影响性能。预计这将影响化学家在该领域的方法开发中实现反应优化的方式，从而促进更广泛地采用环保方法。
• Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: easily available new chiral building blocks
  作者：Jacek Skarżewski、Mariola Zielińska-Błajet、Ilona Turowska-Tyrk

  DOI：10.1016/s0957-4166(01)00330-5

  日期：2001.7

  A facile and enantioselective method for the multigram preparation of the title compounds is described. The Michael addition of thiophenols to chalcones catalyzed by (+)-cinchonine, followed by crystallization, led to the corresponding adducts 2 in up to > 95% e.e. The stereoselective Beckmann rearrangement of the oxime of (+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one 2a gives the anilide of (R)-(+)-3-phenyl-3-phenylsulfanylpropanoic acid (as determined by X-ray analysis) and alcoholysis leads to the corresponding enantiomerically pure ethyl ester. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereoselective thio-Michael addition to chalcones in water catalyzed by bovine serum albumin
  作者：Nicoletta Gaggero、Domenico Carlo Maria Albanese、Giuseppe Celentano、Stefano Banfi、Alice Aresi

  DOI：10.1016/j.tetasy.2011.06.024

  日期：2011.6

  A biomimetic, inexpensive, and simple method for the stereoselective thio-Michael addition of thiols to chalcones has been developed using bovine serum albumin (BSA) as a catalyst. Optically active products are obtained in high yield and with enantiomeric excesses of up to 70%. (C) 2011 Elsevier Ltd. All rights reserved.