methyl (R)-4-methylbenzenesulfinate | 64396-66-3

• 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: methyl (R)-4-methylbenzenesulfinate
• 英文别名: (S)-(-)-methyl p-toluenesulfinate；(-)-methyl toluene-p-sulphinate；(R)-methyl p-toluenesulfinate
• CAS: 64396-66-3
• 化学式: C₈H₁₀O₂S
• 分子量: 170.232
• InChiKey: MGPLBSPZSIFUQX-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  methyl (R)-4-methylbenzenesulfinate 生成 (R)-(+)-phenyl p-tolyl sulfoxide
  参考文献：
  名称：

  HIROI, KUNIO;KITAYAMA, RYUICHI;SATO, SHUKO, SYNTHESIS, BRD, 1983, N 12, 1040-1041

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 16.0h， 生成 methyl (R)-4-methylbenzenesulfinate
  参考文献：
  名称：

  Annunziata, Rita; Cinquini, Mauro; Cozzi, Franco, Journal of the Chemical Society. Perkin transactions I, 1982, p. 339 - 344

  摘要：

  DOI：

文献信息

• Acid Catalyzed Alcoholysis of Sulfinamides: Unusual Stereochemistry, Kinetics and a Question of Mechanism Involving Sulfurane Intermediates and Their Pseudorotation
  作者：Bogdan Bujnicki、Józef Drabowicz、Marian Mikołajczyk

  DOI：10.3390/molecules20022949

  日期：——

  formed in this reaction with a full or predominant inversion of configuration at chiral sulfur or with predominant retention of configuration. The steric course of the reaction depends mainly on the size of the dialkylamido group in the sulfinamides and of the alcohols used as nucleophilic reagents. It has been found that bulky reaction components preferentially form sulfinates with retention of configuration

  旋光性亚磺酸酯的合成已经通过旋光性亚磺酰胺的酸催化醇解完成。在该反应中形成亚磺酸盐，其中在手性硫处构型完全或主要反转，或构型主要保留。反应的空间过程主要取决于亚磺酰胺中的二烷基酰胺基的大小以及用作亲核试剂的醇的大小。已经发现，庞大的反应组分在保留构型的情况下优先形成亚磺酸盐。已经证明，通过向酸性反应介质中添加无机盐，可以将反应的立体化学结果从转化转变为保留，反之亦然。这种典型的双分子亲核取代反应的不同立体化学，
• Chiral sulfinates studied by optical rotation, ECD and VCD: the absolute configuration of a cruciferous phytoalexin brassicanal C
  作者：Tohru Taniguchi、Kenji Monde、Koji Nakanishi、Nina Berova

  DOI：10.1039/b813437e

  日期：——

  The optical rotation, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of chiral sulfinates have been studied experimentally, and analysed by density functional theory calculation, aiming at establishing a reliable and convenient methodology to determine their absolute configuration. Through the study on a model chiral sulfinate with known absolute configuration, (R)-(+)-methyl

  对手性亚磺酸盐的旋光性，电子圆二色性（ECD）和振动圆二色性（VCD）进行了实验研究，并通过密度泛函理论计算进行了分析，目的是建立一种可靠，方便的方法来确定它们的绝对构型。通过对已知绝对构型的模型手性亚磺酸盐（R）-（+）-对甲苯磺酸甲基酯（（R）-（+）-1）的研究，发现每种技术在分配亚磺酸盐的手性方面都是可靠的。然后，我们将这些方法应用于合成制备的十字花科植物抗毒素，芸苔素C（（-）-2），并明确确定其绝对构型为S。还讨论了每种光谱对亚磺酸盐的利弊。
• METHOD FOR PREPARING ENANTIOMER OF SULFOXIDE COMPOUND, AND SYSTEM FOR PREPARING ENANTIOMER
  申请人：Tokyo University of Science Foundation

  公开号：US20220306593A1

  公开（公告）日：2022-09-29

  An enantiomer preparation method in which one enantiomer of a sulfoxide compound is selectively prepared, the sulfoxide compound having a sulfur atom of a sulfoxide group as an asymmetric center, the method including a step A for optically resolving an enantiomer mixture of a sulfoxide compound into one enantiomer and the other enantiomer; a step B for irradiating with light the other enantiomer obtained in step A or step C to racemize the enantiomer; and step C for optically resolving the enantiomer mixture of the sulfoxide compound obtained in step B into one enantiomer and the other enantiomer. A system for preparing an enantiomer which is used in the enantiomer preparation method.

  一种手性亚砜化合物的对映体制备方法，其中选择性地制备亚砜基硫原子作为不对称中心的手性亚砜化合物的一种对映体，该方法包括以下步骤：步骤A，将手性亚砜化合物的对映体混合物光学分离成一种对映体和另一种对映体；步骤B，用光照射步骤A或步骤C中获得的另一种对映体使其消旋；步骤C，将步骤B中获得的手性亚砜化合物的对映体混合物光学分离成一种对映体和另一种对映体。还提供了用于制备对映体的系统，该系统用于上述手性亚砜化合物的对映体制备方法。
• Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)-arylsulfinamides
  作者：Rui-Heng Zhu、Xiao-Xin Shi

  DOI：10.1016/j.tetasy.2011.01.028

  日期：2011.2

  A novel and simple process for the preparation of enantiomerically pure (S(s))-benzenesulfinamide (S(s))-3a, (S(s))-p-toluenesulfinamide (S(s))-3b, (S(s))-p-chloro-benzenesulfinamide (S(s))-3c and (S(s))-p-fluorobenzenesulfinamide (S(s))-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)-arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,S(s))-N-benzyl-N-(1-phenylethyl)-arylsulfinamides (R,S(s))-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,S(s))-1 were then converted into four enantiopure (R(s))-methyl arylsulfinates (R(s))-2, and finally into four enantiopure (S(s))-arylsulfinamides (S(s))-3 in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Bujnicki, Bogdan; Drabowicz, Jozef; Mikolajczyk, Marian, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 419 - 420
  作者：Bujnicki, Bogdan、Drabowicz, Jozef、Mikolajczyk, Marian、Kolbe, Alfred

  DOI：——

  日期：——