(1R,2S,5R)-menthyl (S)-p-bromobenzene sulfinate | 873586-66-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,5R)-menthyl (S)-p-bromobenzene sulfinate
• CAS: 873586-66-4
• 化学式: C₁₆H₂₃BrO₂S
• 分子量: 359.327
• InChiKey: VSYNWPRUJIOSBR-NXOXCILZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-menthyl (S)-p-bromobenzene sulfinate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-p-bromobenzenesulfinamide
  参考文献：
  名称：

  Structural Insight into the Stereoselective Inhibition of MMP-8 by Enantiomeric Sulfonamide Phosphonates

  摘要：

  Potent and selective inhibitors of matrix metalloproteinases (MMPs), a family of zinc proteases that can degrade all the components of the extracellular matrix, could be useful for treatment of diseases such as cancer and arthritis. The most potent MMP inhibitors are based on hydroxamate as zinc-binding group (ZBG). alpha-Arylsulfonylamino phosphonates incorporate a particularly favorable combination of phosphonate as ZBG and arylsulfonylamino backbone so that their affinity exceptionally attains the nanomolar strength frequently observed for hydroxamate analogues. The detailed mode of binding of [1-(4'-methoxybiphenyl-4-sulfonylamino)-2-methylpropyl]phosphonate has been clarified by the crystal structures of the complexes that the R- and S-enantiomers respectively form with MMP-8. The reasons for the preferential MMP-8 inhibition by the R-phosphonate are underlined and the differences in the mode of binding of analogous alpha-arylsulfonylamino hydroxamates and carboxylates are discussed.

  DOI：

  10.1021/jm050787+
• 作为产物：
  描述：

  L-薄荷醇 、 4-溴苯磺酰氯 在 三乙胺 、 三甲氧基磷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以57%的产率得到(1R,2S,5R)-menthyl (S)-p-bromobenzene sulfinate
  参考文献：
  名称：

  基于格利雅试剂对亚磺酰基化合物进行的氧和碳离去基团的连续置换，对二烷基亚砜具有高度立体选择性。

  摘要：

  DOI：

  10.1021/jo010334m

文献信息

• Synthesis and Palladium-Catalyzed Coupling Reactions of Enantiopure <i>p</i>-Bromophenyl Methyl Sulfoximine
  作者：Gae Young Cho、Hiroaki Okamura、Carsten Bolm

  DOI：10.1021/jo047940c

  日期：2005.3.1

  asymmetric synthesis and chemical modification of p-bromophenyl methyl sulfoximine (2) is described. Starting from p-bromophenyl menthyl sulfinate (5), enantiopure 2 can be obtained in a short reaction sequence involving a well-established substitution reaction followed by stereospecific imination with O-mesitylenesulfonylhydroxylamine (MSH). Palladium-catalyzed Buchwald/Hartwig, Suzuki, and Stille

  描述了对-溴苯基甲基亚磺酰亚胺（2）的不对称合成和化学修饰。从对-溴苯基薄荷基亚磺酸盐（5）开始，可以在短的反应序列中获得对映体纯2，所述短的反应序列包括建立良好的取代反应，然后用O-间苯二甲磺酰基羟胺（MSH）进行立体定向亚胺化。钯催化的Buchwald / Hartwig，Suzuki和Stille偶联反应使亚砜亚胺芳基的变化范围很大，否则很难实现。p的并入-吗啉代取代的衍生物成为假三肽证明了该新型亚磺酰亚胺衍生物的适用性。
• Self-assemblies of chiral p-haloaryl sulfoxides through C–H⋯O short contacts and halogen involving interactions
  作者：Francesco Naso、Cosimo Cardellicchio、Maria Annunziata M. Capozzi、Francesco Capitelli、Valerio Bertolasi

  DOI：10.1039/b607545b

  日期：——

  determination of four crystals of alkyl or aryl p-haloaryl sulfoxides is reported. Intramolecular short contacts between the ortho-hydrogen of the aryl ring and the oxygen of the sulfinyl group were found to determine the conformations of the sulfoxides. On the other hand, in the absence of classical hydrogen bond donors, crystal packing arrangements are the results of intermolecular aryl hydrogen–oxygen short

  单晶 X射线结构测定 的四个晶体 烷基或报道了芳基对-卤代芳基亚砜。分子间原氢之间的分子内短接触芳基 环和氧气 亚磺酰基 被发现以确定构象 亚砜。另一方面，在没有经典氢键供体的情况下，晶体堆积的排列是分子间的结果。芳基 氢氧短接触以及涉及的相互作用 卤素原子。从被调查者的结构比较亚砜 根据其他文献数据，这些类型化合物的晶体堆积似乎源自不同相互作用之间的复杂平衡。