Benzenesulfinamide, N-methyl-, (R)- | 33957-73-2

• 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: Benzenesulfinamide, N-methyl-, (R)-
• 英文别名: (R)-N-methylbenzenesulfinamide
• CAS: 33957-73-2；69726-27-8；84413-63-8；33993-55-4
• 化学式: C₇H₉NOS
• 分子量: 155.221
• InChiKey: BNRSRAAQDITUDU-SNVBAGLBSA-N

物化性质

• 沸点：
  282.2±23.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium phenoxide 、 Benzenesulfinamide, N-methyl-, (R)- 生成 Phenyl-N-methylbenzolsulfonimidat
  参考文献：
  名称：

  Chemistry of sulfoxides and related compounds. XXXIII. Stereochemistry of substitution at tetracoordinate hexavalent sulfur. Nucleophilic reactions at sulfur in sulfonimidoyl compounds

  摘要：

  DOI：

  10.1021/ja00749a085
• 作为产物：
  描述：

  (-)-(R)-N,S-dimethyl-S-phenylsulfoximine 在 正丁基锂 、 三甲基氯硅烷 、 二甲基硫 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 10.0h， 生成 Benzenesulfinamide, N-methyl-, (R)-
  参考文献：
  名称：

  Bund, Joerg; Gais, Hans-Joachim; Schmitz, Elmar, European Journal of Organic Chemistry, 1998, # 7, p. 1319 - 1335

  摘要：

  DOI：

文献信息

• Asymmetric Synthesis of Densely Functionalized Medium-Ring Carbocycles and Lactones through Modular Assembly and Ring-Closing Metathesis of Sulfoximine-Substituted Trienes and Dienynes
  作者：Michal Lejkowski、Prabal Banerjee、Sabine Schüller、Alexander Münch、Jan Runsink、Cornelia Vermeeren、Hans-Joachim Gais

  DOI：10.1002/chem.201103060

  日期：2012.3.19

  (S)‐diastereomer delivered in a cascade of cross metathesis and RCDEM 22‐membered macrocycles. RCDEM of cyclic trienes furnished bicyclic carbocycles with a bicyclo[7.4.0]tridecane and bicyclo[9.4.0]pentadecane skeleton. Selective transformations of the sulfoximine‐ and bissilyloxy‐substituted carbocycles were performed including deprotection, cross‐coupling reaction and reduction of the sulfoximine moiety

  已经开发出稠密官能化的7-11元碳环和9-11元内酯的不对称合成。它的关键步骤是用模块组装硫磺亚胺取代的C和O系三烯和C系二烯，以及它们在Ru催化下的闭环二烯和烯炔复分解（RCDEM和RCEYM）。C链状三烯和二烯的合成包括以下步骤：1）对映体纯的钛酸烯丙基亚砜基亚砜与不饱和醛的羟烷基化，2）烯基亚砜基亚砜的α-锂化，3）α的烷基化，羟基烷基化，甲酰化和酰化-硫代链烯基亚砜亚胺，以及4）将格氏试剂添加到α-甲酰基（酰基）烯基亚砜基亚砜。亚砜亚胺基团在步骤1）和4）中提供了高不对称诱导作用。用第二代Ru催化剂对亚砜亚胺取代的三烯进行的RCDEM立体选择性地提供了相应的功能化7-11元碳环。非对映异构的甲硅烷氧基取代的1,6,12-三烯的RCDEM显示出反应性上的有趣差异。而（R）-非对映异构体给出了11元的碳环，（S）非对映异构体以交叉复分解和RCDEM 22元大环化合物的级联传递。环状三烯的RCDEM为双环碳环提供了双环[7
• Double metal-catalyzed cross-coupling reactions of alkenyl sulfoximines with diorganozinc reagents: Synthesis of optically active axial chiral allylic silanes
  作者：Hans-Joachim Gais、Gred Bülow

  DOI：10.1016/s0040-4039(00)93968-6

  日期：1992.1

  Nickel- and magnesium-catalyzed cross-coupling reaction of the alkenyl sulfoximine 5 with the pure diorganozinc reagents 6a and 6b gave the optically active allylic silanes 7a and 7b, respectively, Single metal catalysis was sufficient for the substitution of the bromide rac-9 whereas the sulfone rac-10 did neither under the conditions of single nor under that of double metal catalysis react with 6a

  链烯基硫肟基亚胺5与纯二有机锌试剂6a和6b的镍和镁催化的交叉偶联反应分别得到光学活性的烯丙基硅烷7a和7b，单金属催化足以取代溴化物rac- 9，而砜rac- 10在单金属催化和双金属催化条件下均未与6a反应。
• Nucleophilic substitution at sulfur in sulfonimidoyl compounds: synthesis of sulfoximines
  作者：Carl R. Johnson、Ernst U. Jonsson、Anthony Wambsgans

  DOI：10.1021/jo01327a002

  日期：1979.6
• Asymmetric Synthesis of Fused Bicyclic α-Amino Acids Having a Hexahydro-cyclopenta[<i>c</i>]pyridine Skeleton via Intramolecular Pauson−Khand Reaction of 1-Sulfonimidoyl-Substituted 5-Azaoct-1-en-7-ynes
  作者：Markus Günter、Hans-Joachim Gais

  DOI：10.1021/jo030171x

  日期：2003.10.1

  An asymmetric synthesis of fused bicyclic amino acids having a hexahydro-cyclopenta[c]pyridine skeleton and carrying besides an enone structural element a substituent at the beta-position is described. The key steps of the synthesis are a highly selective allylation of N-tert-butylsulfonyl imino ester with bis(allylsulfoximine)titanium complexes and a highly diastereoselective Pauson-Khand cycloaddition of sulfonimidoyl-substituted gamma,delta-unsaturated alpha-amino acid esters carrying a substituent at the beta-position and a propargyl group at the N-atom. The cyclization is accompanied by a reductive cleavage of the sulfoximine group of the primary cyclization product. Surprisingly, the removal of the sulfoximine group proceeds with inversion of the configuration at the S-atom and gives N-methyl-phenylsulfinamide with greater than or equal to98% ee. Deprotection of the bicyclic N-tert-butylsulfonyl-protected amino acid ester was accomplished through treatment with CF3SO3H under anhydrous conditions. The enantio- and diastereomerically pure sulfoximine-substituted gamma,delta-unsaturated alpha-amino acid esters used as starting material were obtained through a highly regio- and diastereoselective allylation of N-tert-butylsulfonyl imino ester with acyclic bis(allylsulfoximine)titanium complexes, described previously.
• Bund, Joerg; Gais, Hans-Joachim; Schmitz, Elmar, European Journal of Organic Chemistry, 1998, # 7, p. 1319 - 1335
  作者：Bund, Joerg、Gais, Hans-Joachim、Schmitz, Elmar、Erdelmeier, Irene、Raabe, Gerhard

  DOI：——

  日期：——