3-phenyl-3-(phenylthio)propanenitrile | 69333-49-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-phenyl-3-(phenylthio)propanenitrile
• 英文别名: 3-Phenyl-3-phenylsulfanylpropanenitrile
• CAS: 69333-49-9
• 化学式: C₁₅H₁₃NS
• 分子量: 239.341
• InChiKey: STQIIODIIQLZJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-3-(phenylthio)propanenitrile 在 ammonium heptamolybdate 双氧水 作用下， 生成 3-phenyl-3-(phenylsulfonyl)propanenitrile
  参考文献：
  名称：

  Redman,R.P. et al., Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144

  摘要：

  DOI：
• 作为产物：
  描述：

  (肉)桂腈 、 苯硫酚 在 lithium hydroxide 作用下， 以95%的产率得到3-phenyl-3-(phenylthio)propanenitrile
  参考文献：
  名称：

  炔丙醇与盐酸羟胺的级联反应：轻松合成α，β-不饱和肟和腈

  摘要：

  我们已经开发了一种简便实用的方法，可在无金属条件下，用容易得到的炔丙醇与盐酸羟胺（NH 2 OH·HCl）合成α，β-不饱和肟和腈。通过使用或不使用对甲苯磺酰氯（p -TsCl）作为脱水促进剂，可以分别通过三步一锅法或两步一锅法以中等至优异的产率获得所需的腈或肟。具有良好的功能组兼容性。

  DOI：

  10.1016/j.tet.2016.09.010

文献信息

• Sulphide as a leaving group: highly stereoselective bromination of alkyl phenyl sulphides
  作者：Daniele Canestrari、Caterina Cioffi、Ilaria Biancofiore、Stefano Lancianesi、Lorenza Ghisu、Manuel Ruether、John O'Brien、Mauro F. A. Adamo、Hasim Ibrahim

  DOI：10.1039/c9sc03560e

  日期：——

  A conceptionally novel nucleophilic substitution approach to synthetically important alkyl bromides is presented. Using molecular bromine (Br2), readily available secondary benzyl and tertiary alkyl phenyl sulphides are converted into the corresponding bromides under exceptionally mild, acid- and base-free reaction conditions. This simple transformation allows the isolation of elimination sensitive

  提出了一种概念上新颖的对重要合成烷基溴的亲核取代方法。使用分子溴（Br2），在异常温和，无酸和无碱的反应条件下，容易获得的仲苄基和叔烷基苯基硫化物转化为相应的溴化物。这种简单的转化可以以高收率和高纯度分离出对消除敏感的苄基β-溴羰基和腈化合物。值得注意的是，质子官能团（例如酸和醇）是可以容忍的。通过不对称磺胺-迈克尔加成反应很容易制得的对映体富集的苄基β-磺基酯，可产生相应的具有高立体选择性的倒置溴化物，在-40°C时达到完全对映体特异性。显着地，报道的苄基β-溴代酯可以在没有消旋作用的情况下在-20°C下长时间保存。一锅法制备90％ee的γ-叠氮基醇（S）-5证明了其合成潜力。NMR研究表明，最初形成了硫化物溴加合物，而该加合物又与假定的经历C-Br键形成的二溴硫丙烷中间体处于平衡状态。
• High-Pressure Induced Domino-Horner-Wadsworth-Emmons (HWE) - Michael Reactions
  作者：Senay Has-Becker、Kerstin Bodmann、Reinhard Kreuder、Gabriella Santoni、Tobias Rein、Oliver Reiser

  DOI：10.1055/s-2001-16786

  日期：——

  A new protocol for the alkenylation of carbonyl compounds with phosphonates (Horner-Wadsworth-Emmons reaction) is described. Aldehydes react with phosphonates already at room temperature in the presence of triethylamine without further activation by Lewis-acids if high-pressure (8 kbar) is applied to the system. Based on this protocol a domino process was developed combining the HWE reaction with a Michael reaction, thus allowing the one-pot synthesis of β-amino esters, β-thio esters or β-thio nitriles.

  本文介绍了羰基化合物与膦酸盐发生烯化反应（Horner-Wadsworth-Emmons 反应）的新方案。如果在体系中施加高压（8 kbar），醛与膦酸盐在室温下就能在三乙胺存在下发生反应，而无需路易斯酸进一步活化。在此基础上，我们开发了一种多米诺工艺，将 HWE 反应与迈克尔反应相结合，从而实现了 δ-氨基酯、δ-硫代酯或δ-硫代腈纶的一次合成。
• .alpha.,.beta.-Unsaturated Nitriles: An Efficient Conjugate Addition with Potassium Benzeneselenolate and Potassium Benzenesulfenylate
  作者：Fraser F. Fleming、Joshua J. Pak

  DOI：10.1021/jo00118a060

  日期：1995.6
• [EN] FLUORINATION PROCESS<br/>[FR] PROCÉDÉ DE FLUORATION
  申请人：[en]ROYAL COLLEGE OF SURGEONS IN IRELAND

  公开号：WO2024028729A1

  公开（公告）日：2024-02-08

  The present disclosure relates to processes for the fluorination of molecules. One aspect provides a process for incorporating a fluorine atom into a molecule, said process comprising converting a compound of formula X—SG into a compound of formula X—F, wherein G is an optionally substituted C1-C6alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group, and X is an organic group; and wherein the SG group is attached to a secondary or tertiary carbon atom in the organic group X; said process comprising treating said compound of formula X—SG with (i) an activator compound selected from the group consisting of N-halosuccinimides, N-halobenzenesulfonimides, N-halobenzenesulfonamides, dialkylaminodihalosulfinium salts, heterocyclylaminodihalosulfinium salts, dialkylaminosulfur trihalides, XeF2, difluoroiodotoluene, di-and tri-bromoisocyanuric acids, bromine, chlorine, hypervalent iodine compounds with I2; and other sources of Br+, Cl+, F+, l+, bromonium, iodonium, or chloronium; and (ii) a source of fluoride. Uses of the process in the preparation of various fluorinated molecules as well as uses of certain compounds as intermediates in the processes of the present disclosure are also provided.