(1R,2S,5R)-(-)-menthyl (S)-4-methoxyphenylsulfinate | 1942-34-3

• 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)-4-methoxyphenylsulfinate
• 英文别名: R_S-l-menthyl p-methoxybenzenesulfinate；(S)-(-)-menthyl p-methoxybenzenesulfinate；(-)-(S)-p-methoxyphenyl menthylsulfinate；(S)-L-menthyl p-methoxybenzenesulfinate；l-Menthyl (S)-4-methoxyphenylsulfinate；(R)-menthyl p-methoxybenzenesulfinate
• CAS: 1942-34-3
• 化学式: C₁₇H₂₆O₃S
• 分子量: 310.458
• InChiKey: KMPNHVLRKYERFG-YFPSAGDSSA-N

物化性质

• 沸点：
  422.5±47.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-(-)-menthyl (S)-4-methoxyphenylsulfinate 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成
  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：

  p-hydroxybenzenesulfinic acid 在 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,2S,5R)-(-)-menthyl (S)-4-methoxyphenylsulfinate
  参考文献：
  名称：

  固相合成亚磺酸薄荷酯和亚砜

  摘要：

  对羟基苯磺酸亚锡酯很容易与Wang树脂连接。生成的亚磺酸盐与格氏试剂和烯醇钾或烯醇锂反应生成相应的亚砜或β-酮亚砜，从而可以研究用于固相合成的亚砜的化学性质。

  DOI：

  10.1016/s0040-4039(01)01978-5

文献信息

• C2-Symmetric Chiral Disulfoxide Ligands in Rhodium-Catalyzed 1,4-Addition: From Ligand Synthesis to the Enantioselection Pathway
  作者：Ronaldo Mariz、Albert Poater、Michele Gatti、Emma Drinkel、Justus J. Bürgi、Xinjun Luan、Sascha Blumentritt、Anthony Linden、Luigi Cavallo、Reto Dorta

  DOI：10.1002/chem.201001749

  日期：2010.12.27

  Their synthesis, optical purity, electronic properties, and catalytic behavior in the prototypical rhodium‐catalyzed 1,4‐addition of phenylboronic acid to 2‐cyclohexen‐1‐one are presented through an in depth study of this ligand class. Density functional theory calculations on the step of the catalytic cycle that determines the enantioselectivity are presented and reinforce the first hypothetical explanations

  通过使用Andersen方法合成了具有联芳基阻转异构体骨架的手性C 2对称二亚砜配体家族。完整的表征包括对所有配体及其某些铑配合物的X射线晶体学研究。通过对该配体类别的深入研究，介绍了它们的合成，光学纯度，电子性质以及在典型的铑催化的苯基硼酸向2-环己烯-1-酮的1,4加成中的催化行为。提出了确定对映选择性的催化循环步骤的密度泛函理论计算，并加强了观察到的高水平不对称诱导的第一个假设解释。
• A Class of Benzene Backbone-Based Olefin–Sulfoxide Ligands for Rh-Catalyzed Enantioselective Addition of Arylboronic Acids to Enones
  作者：Feng Xue、Xincheng Li、Boshun Wan

  DOI：10.1021/jo2011472

  日期：2011.9.2

  A class of readily available and easily tunable benzene backbone-based olefin–sulfoxide ligands was developed for the rhodium-catalyzed asymmetric conjugate addition reaction of arylboronic acids to enones with up to 97% yield and 97% ee.

  针对铑催化的芳基硼酸与烯酮的不对称共轭加成反应，开发了一种易于获得且易于调节的基于苯骨架的烯烃-亚砜配体，产率高达97％，ee高达97％。
• Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization
  作者：Barry M Trost、Michael C Ryan、Meera Rao

  DOI：10.3762/bjoc.12.110

  日期：——

  A full account of our efforts toward an asymmetric redox bicycloisomerization reaction is presented in this article. Cyclopentadienylruthenium (CpRu) complexes containing tethered chiral sulfoxides were synthesized via an oxidative [3 + 2] cycloaddition reaction between an alkyne and an allylruthenium complex. Sulfoxide complex 1 containing a p-anisole moiety on its sulfoxide proved to be the most efficient and selective catalyst for the asymmetric redox bicycloisomerization of 1,6- and 1,7-enynes. This complex was used to synthesize a broad array of [3.1.0] and [4.1.0] bicycles. Sulfonamide- and phosphoramidate-containing products could be deprotected under reducing conditions. Catalysis performed with enantiomerically enriched propargyl alcohols revealed a matched/mismatched effect that was strongly dependent on the nature of the solvent.

  本文介绍了我们在不对称氧化还原双环异构化反应方面的努力。通过炔烃和烯丙基钌配合物之间的氧化性[3+2]环加成反应合成了含有连接手性亚砜的环戊二烯基钌（CpRu）配合物。其中，含有苯甲醚基的亚砜的复合物1被证明是对于1,6-和1,7-烯炔的不对称氧化还原双环异构化反应最有效和选择性最高的催化剂。该复合物被用于合成广泛的[3.1.0]和[4.1.0]自行车。磺酰胺和磷酰胺酰基含有的产物可以在还原条件下去保护基。使用对映富集的丙炔醇进行的催化反应表明，在溶剂的性质强烈依赖的情况下，存在匹配/不匹配效应。
• An improved and efficient procedure for the preparation of chiral sulfinates from sulfonyl chloride using triphenylphosphine
  作者：Yoshihiko Watanabe、Nobuyuki Mase、Moto-aki Tateyama、Takeshi Toru

  DOI：10.1016/s0957-4166(99)00066-x

  日期：1999.2

  An improved procedure of the Sharpless method for the preparation of chiral sulfinates by triphenylphosphine is described. A mixture of sulfonyl chlorides and diacetone-d-glucose or l-menthol in the presence of triethylamine was treated with triphenylphosphine in CH2Cl2 at 0°C to give the sulfinates in good yields.

  描述了通过三苯基膦制备手性亚磺酸盐的Sharpless方法的改进方法。在三乙胺存在下，将磺酰氯和双丙酮-d-葡萄糖或1-薄荷醇的混合物在0℃下在CH 2 Cl 2中用三苯基膦处理，以良好的产率得到亚磺酸盐。
• An efficient and novel method for the synthesis of sulfinate esters under solvent-free conditions
  作者：Abdol R. Hajipour、Ali R. Falahati、Arnold E. Ruoho

  DOI：10.1016/j.tetlet.2006.02.080

  日期：2006.4

  The present letter describes a reliable one-stage process for the preparation of sulfinate esters from the corresponding sulfinic acid and alcohols in the presence of N,N'-dicyclohexylcarbodiimide (DCC) under solvent-free conditions. (c) 2006 Elsevier Ltd. All rights reserved.