1-(fluoromethyl)-2-[(S)-p-tolylsulfinyl]benzene | 1311404-00-8

• 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: 1-(fluoromethyl)-2-[(S)-p-tolylsulfinyl]benzene
• 英文别名: (S)-2-(p-tolylsulfinyl)benzyl fluoride；1-(fluoromethyl)-2-[(S)-(4-methylphenyl)sulfinyl]benzene
• CAS: 1311404-00-8
• 化学式: C₁₄H₁₃FOS
• 分子量: 248.321
• InChiKey: ZBONEKGJBJEVGE-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(fluoromethyl)-2-[(S)-p-tolylsulfinyl]benzene 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.6h， 生成 (2R,3R)-3-fluoro-2,3-diphenylpropyl phenyl sulfone
  参考文献：
  名称：

  Stereocontrolled Fluorobenzylation of Vinyl Sulfones and α,β-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis of Functionalized Enantiomerically Pure Benzylic Fluorides

  摘要：

  A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with beta-substituted vinyl sulfones and alpha,beta-unsaturated esters. Reactions afford easily separable mixtures of two epimers differing in the configuration of the center derived from the Michael acceptor (up to 98% de). They can be easily converted into enantiomerically pure gamma-fluorinated gamma-phenylsulfones and gamma-phenylesters bearing two chiral centers.

  DOI：

  10.1021/jo300174k
• 作为产物：
  描述：

  (S)‐2‐(p‐tolylsulfinyl)benzyl 4‐methylbenzenesulfonate 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 以88%的产率得到1-(fluoromethyl)-2-[(S)-p-tolylsulfinyl]benzene
  参考文献：
  名称：

  手性一氟苄基碳负离子：对映纯β-氟代β-苯基乙胺的合成

  摘要：

  稳定化的负碳离子monofluorobenzyl由远程纯手性亚磺酰基的手段和其与完全立体选择性反应制备ñ - p -tolylsulfinylimines中描述。使用这些反应后，同时用t BuLi除去两个手性助剂，这在苄基位置没有差向异构发生，为对映体纯的β-氟化的β-苯基乙胺提供了最快的进入途径。

  DOI：

  10.1002/chem.201100455

文献信息

• Asymmetric Nucleophilic Monofluorobenzylation of Carbonyl Compounds: Synthesis of Enantiopure vic-Fluorohydrins and α-Fluorobenzylketones
  作者：Yolanda Arroyo、M. Ascensión Sanz-Tejedor、Alejandro Parra、José Luis García Ruano

  DOI：10.1002/chem.201103919

  日期：2012.4.23

  Asymmetric nucleophilic monofluoroalkylation of a broad range of aldehydes with an α‐fluoro‐γ‐sulfinylbenzyl carbanion takes place with complete control of the facial selectivity at the carbanion and good to high anti‐diastereoselectivity to give easily separable mixtures of two optically pure 1,2‐fluorohydrin derivatives (up to 24:1 anti/syn). Separation and removal of the p‐tolylsulfinyl group with

  范围广泛的与α氟γ-sulfinylbenzyl碳负离子醛的不对称亲核monofluoroalkylation发生与负碳离子和良好的高面部选择性的完全控制抗-diastereoselectivity，得到两种旋光纯1,2-易于分离的混合物‐氟代醇衍生物（最多24：1 anti / syn）。用t BuLi分离和除去对甲苯基亚磺酰基可提供对映体纯的抗1,2-二取代-1,2-氟代醇，而α-氟苄基酮可通过混合物的脱亚磺酰化后再进行吡啶鎓氯代铬酸铬的氧化而制得（单锅）。过程）。
• Asymmetric Nucleophilic Monofluorobenzylation of Allyl and Propargyl Halides Mediated by a Remote Sulfinyl Group: Synthesis of Homoallylic and Homopropargylic Fluorides
  作者：Yolanda Arroyo、M. Ascensión Sanz-Tejedor、Alejandro Parra、Inés Alonso、José Luis García Ruano

  DOI：10.1021/jo501096f

  日期：2014.8.1

  Fluorinated 2(p-tolylsulfinyl)benzyl carbanions react with allyl and propargyl halides in a highly stereoselective way, providing homoallylic and homopropargylic fluorides, respectively, with high optical purity. Theoretical calculations found transition states for these transformations whose relative stabilities are consistent with the experimentally observed stereoselectivity.
• Stereocontrolled Fluorobenzylation of Vinyl Sulfones and α,β-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis of Functionalized Enantiomerically Pure Benzylic Fluorides
  作者：José Luis García Ruano、José Antonio Fernández-Salas、M. Carmen Maestro

  DOI：10.1021/jo300174k

  日期：2012.3.16

  A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with beta-substituted vinyl sulfones and alpha,beta-unsaturated esters. Reactions afford easily separable mixtures of two epimers differing in the configuration of the center derived from the Michael acceptor (up to 98% de). They can be easily converted into enantiomerically pure gamma-fluorinated gamma-phenylsulfones and gamma-phenylesters bearing two chiral centers.
• Chiral Monofluorobenzyl Carbanions: Synthesis of Enantiopure β‐Fluorinated β‐Phenylethylamines
  作者：José L. García Ruano、Alejandro Parra、Inés Alonso、Santos Fustero、Carlos del Pozo、Yolanda Arroyo、Ascensión Sanz‐Tejedor

  DOI：10.1002/chem.201100455

  日期：2011.5.23

  monofluorobenzyl carbanion by means of a remote homochiral sulfinyl group and its completely stereoselective reactions with N‐p‐tolylsulfinylimines are described. The use of these reactions followed by the simultaneous removal of both chiral auxiliaries with tBuLi, which occurs without epimerization at the benzylic position, provides the quickest entry to enantiomerically pure β‐fluorinated β‐phenylethylamines

  稳定化的负碳离子monofluorobenzyl由远程纯手性亚磺酰基的手段和其与完全立体选择性反应制备ñ - p -tolylsulfinylimines中描述。使用这些反应后，同时用t BuLi除去两个手性助剂，这在苄基位置没有差向异构发生，为对映体纯的β-氟化的β-苯基乙胺提供了最快的进入途径。