(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-4-bromobenzenesulfinate | 129470-14-0

• 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)-2-isopropyl-5-methylcyclohexyl (S)-4-bromobenzenesulfinate
• 英文别名: (1R,2S,5R)-(-)-menthyl (S_S)-4-bromobenzenesulfinate；l-Menthyl (S)-4-bromophenylsulfinate；menthyl (S)-p-bromobenzenesulfinate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (S)-4-bromobenzenesulfinate
• CAS: 129470-14-0
• 化学式: C₁₆H₂₃BrO₂S
• 分子量: 359.327
• InChiKey: VSYNWPRUJIOSBR-MFHIXDMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-4-bromobenzenesulfinate 在 sodium tetrahydroborate 、 四氯化钛 、 lithium diisopropyl amide 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 1-Bromo-4-((S)-1-methyl-octylsulfanyl)-benzene
  参考文献：
  名称：

  Nishide, Kiyoharu; Nakayama, Akiko; Kusumoto, Tetsuo, Chemistry Letters, 1990, # 4, p. 623 - 626

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯磺酰氯 在 sodium sulfite 作用下， 生成 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (S)-4-bromobenzenesulfinate
  参考文献：
  名称：

  Nishide, Kiyoharu; Nakayama, Akiko; Kusumoto, Tetsuo, Chemistry Letters, 1990, # 4, p. 623 - 626

  摘要：

  DOI：

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。
• Chiral β-Sulfinylamines as Ligands for Enantioselective Addition of Diethylzinc to Benzaldehyde
  作者：Wing Hong Chan、Albert W. M. Lee、Jing Lin

  DOI：10.1039/a808205g

  日期：——

  Chiral β-sulfinylamines 4a, 6a, 6b, 8a, 8b and 9b were synthesized and assessed in the enantioselective addition of diethylzinc to benzaldehyde.

  合成了手性 β-亚磺胺 4a、6a、6b、8a、8b 和 9b，并在二乙基锌对苯甲醛的对映选择性加成中进行了评估。
• Asymmetric Allylic C–H Alkylation via Palladium(II)/<i>cis</i>-ArSOX Catalysis
  作者：Wei Liu、Siraj Z. Ali、Stephen E. Ammann、M. Christina White

  DOI：10.1021/jacs.8b05668

  日期：2018.8.29

  asymmetric C-H alkylation of terminal olefins with a variety of synthetically versatile nucleophiles. The modular, tunable, and oxidatively stable ArSOX scaffold is key to the unprecedented broad scope and high enantioselectivity (37 examples, avg. > 90% ee). Pd(II)/ cis-ArSOX is unique in its ability to effect high reactivity and catalyst-controlled diastereoselectivity on the alkylation of aliphatic

  我们报告了 Pd(II)/顺式-芳基亚砜-恶唑啉 (cis-ArSOX) 催化剂的开发，用于末端烯烃的不对称 CH 烷基化与各种合成通用亲核试剂。模块化、可调且氧化稳定的 ArSOX 支架是前所未有的广泛范围和高对映选择性的关键（37 个例子，平均 > 90% ee）。Pd(II)/cis-ArSOX 的独特之处在于它能够对脂肪族烯烃的烷基化产生高反应性和催化剂控制的非对映选择性。我们预计这种新的手性配体类别将用于其他在氧化条件下运行的过渡金属催化过程。
• Structural Insight into the Stereoselective Inhibition of MMP-8 by Enantiomeric Sulfonamide Phosphonates
  作者：Giorgio Pochetti、Enrico Gavuzzo、Cristina Campestre、Mariangela Agamennone、Paolo Tortorella、Valerio Consalvi、Carlo Gallina、Oliver Hiller、Harald Tschesche、Paul A. Tucker、Fernando Mazza

  DOI：10.1021/jm050787+

  日期：2006.2.1

  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.
• Nishide, Kiyoharu; Nakayama, Akiko; Kusumoto, Tetsuo, Chemistry Letters, 1990, # 4, p. 623 - 626
  作者：Nishide, Kiyoharu、Nakayama, Akiko、Kusumoto, Tetsuo、Hiyama, Tamejiro、Takehara, Sadao、et al.

  DOI：——

  日期：——