(S)-N-benzylidene-4-toluenesulfinamide | 153277-49-7

• 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: (S)-N-benzylidene-4-toluenesulfinamide
• 英文别名: (S)-N-benzylidene-4-methylbenzenesulfinamide；(S)-N-benzylidene-p-toluenesulfinamide
• CAS: 153277-49-7
• 化学式: C₁₄H₁₃NOS
• 分子量: 243.329
• InChiKey: DXUXJHYSHVJFKY-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-benzylidene-4-toluenesulfinamide 在 叔丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.67h， 生成 (S)-4-methyl-N-((1R,2R)-2-methyl-1,2,4-triphenyl-but-3-yn-1-yl)benzenesulfinamide
  参考文献：
  名称：

  Stereocontrolled Addition of Scrambling ortho-Sulfinyl Carbanions: Easy Access to Homopropargylamines and α-Allenylamines

  摘要：

  An unprecedented behavior of ortho-sulfinylpropargyl carbanions in the presence of optically active sulfinylimines affords two different families of compounds: this peculiar chemodivergency is importantly affected by the nature of the employed base, and assisted by the configuration of the electrophile, displaying no alteration in the stereocontrol of both reactions. alpha-Allenylamines are formed exclusively, using R-sulfinyl aldimines as electrophiles, while homopropargylamines result when S-sulfinyl aldimines are employed.

  DOI：

  10.1021/acs.orglett.0c00625
• 作为产物：
  描述：

  苯甲醛 在 三甲基氯硅烷 作用下， 以 乙醚 、 二氯甲烷-D2 为溶剂， 反应 18.0h， 生成 (S)-N-benzylidene-4-toluenesulfinamide
  参考文献：
  名称：

  A General Aminocatalytic Method for the Synthesis of Aldimines

  摘要：

  A general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing the NH2 group in the presence of pyrrolidine as a catalyst has been developed. These organocatalytic reactions, based on the application of the concept of nucleophilic catalysis, proceed with outstanding yields in the absence of acids and metals under simple conditions and minimum experimental manipulation. The method has been mainly applied to the synthesis of N-sulfinyl and N-sulfonyl imines, but its general validity has been proven with the preparation of representative N-phosphinoyl, N-alkyl, and N-aryl imines. These unprecedented reactions, which presumably occur via iminium activation without requiring acidic conditions, are an interesting and competitive alternative to the classical methods for preparing aldimines.

  DOI：

  10.1021/ja4111418

文献信息

• 1,8-Diazabicyclo[5.4.0]undec-7-ene-mediated formation of <i>N</i>-sulfinyl imines
  作者：Manjunatha M Ramaiah、Priya Babu Shubha、Pavan Kumar Prabhala、Nanjunda Swamy Shivananju

  DOI：10.1177/1747519819884146

  日期：2020.1

  A facile and efficient method was developed for the preparation of a variety of aryl, heteroaryl, and alkyl N-sulfinyl imines using 1,8-diazabicyclo[5.4.0]undec-7-ene. In addition to tert-butanesulfinamide, the condensation is also effective with p-toluenesulfinamide. The reaction was performed at room temperature and produces the corresponding N-sulfinyl imines in excellent yields in the absence of

  开发了一种使用 1,8-二氮杂双环 [5.4.0] undec-7-ene 制备各种芳基、杂芳基和烷基 N-亚磺酰基亚胺的简便有效的方法。除叔丁烷亚磺酰胺外，缩合对甲苯亚磺酰胺也有效。该反应在室温下进行，并在不存在酸、金属和添加剂的情况下以极好的收率产生相应的 N-亚磺酰基亚胺。该方法也可用于以克规模制备 N-亚磺酰基亚胺。使用芳基和杂芳基醇与叔丁烷亚磺酰胺和对甲苯亚磺酰胺在室温下进行一锅合成，得到相应的 N-亚磺酰亚胺，收率良好。
• Asymmetric synthesis of N-tosyl amino acids from N-sulfinyl α-amino-1,3-dithioketals
  作者：Franklin A. Davis、Tokala Ramachandar、Jing Chai、Hiu Qiu

  DOI：10.3998/ark.5550190.0011.804

  日期：——

  Hydrolysis of diastereomerically pure N-sulfinyl -amino-1,3-dithianes with 1,3-dibromo-5,5dimethylhydantoin gives N-tosyl -amino aldehydes which when subjected to a Pinnick-type oxidation gave N-tosyl -amino acids without epimerization.

  用 1,3-二溴-5,5 二甲基乙内酰脲水解非对映体纯 N-亚磺酰基 α-氨基-1,3-二噻烷生成 N-甲苯磺酰基 α-氨基醛，当进行 Pinnick 型氧化时生成 N-甲苯磺酰基 α-氨基没有差向异构化的酸。
• Microwave-Assisted Solvent-Free Synthesis of Enantiomerically Pure <i>N</i>-(<i>tert</i>-Butylsulfinyl)imines
  作者：Juan F. Collados、Estefanía Toledano、David Guijarro、Miguel Yus

  DOI：10.1021/jo300919x

  日期：2012.7.6

  environmentally friendly, and very efficient procedure for the synthesis of optically pure N-(tert-butylsulfinyl)imines has been developed with microwave-promoted condensation of aldehydes and ketones using (R)-2-methylpropane-2-sulfinamide in the presence of Ti(OEt)4, under solvent-free conditions. This procedure allows for the preparation of a variety of sulfinyl aldimines with excellent yields and purities

  已经开发了一种简单，环保且非常有效的合成光学纯N-（叔丁基亚磺酰基）亚胺的方法，该方法是在（R）-2-甲基丙烷-2-亚磺酰胺中使用微波促进醛和酮的缩合反应。在无溶剂条件下存在Ti（OEt）4。该方法允许仅在10分钟内以优异的收率和纯度制备各种亚磺酰基醛亚胺，从而无需进一步纯化亚胺。通过将反应时间延长至1小时，还以良好的产率制备了几种亚磺酰基酮亚胺。事实证明，该方法对于合成芳族，杂芳族和脂族N同样有效-（叔丁基亚磺酰基）亚胺。还显示常规加热对于促进这些反应是有用的，特别是对于醛亚胺的合成。
• Stereoselective Synthesis of β-Amino Acid Derivatives by Asymmetric Mannich Reaction in Flow
  作者：Masahito Yoshida、Koji Umeda、Takayuki Doi

  DOI：10.1246/bcsj.20170194

  日期：2017.10.15

  A continuous flow synthesis of β-amino acid derivatives has been demonstrated using an asymmetric Mannich reaction. An enolate of tert-butyl acetate was successfully prepared in 10 s at room temperature in a flow reactor, and the desired β-amino acid derivatives were stereoselectively obtained within a short residence time (40 s) in moderate-to-good yields. Sequential N-alkylation of the Mannich product

  已经使用不对称曼尼希反应证明了 β-氨基酸衍生物的连续流动合成。在室温下，在流动反应器中，在 10 秒内成功制备了乙酸叔丁酯的烯醇化物，并在较短的停留时间（40 秒）内立体选择性地以中等至良好的收率获得了所需的 β-氨基酸衍生物。在流动反应器中曼尼希产品的连续 N-烷基化也在 DMPU 的存在下实现，以良好的产率提供 N-烷基化的 β-氨基酸衍生物。
• Direct and practical Gilman-Speeter synthesis of 3,4-trisubstituted β-lactams via the Thorpe-Ingold effect
  作者：Maria Panagiotou、Vasileios Demos、Plato Α. Magriotis

  DOI：10.1016/j.tetlet.2020.152375

  日期：2020.10

  A highly efficient Gilman-Speeter synthesis of 3,4-trisubstituted β-lactams possessing a 4-aryl substituent is described, employing a direct, uncatalyzed Mannich reaction between TMS imines and TMS ketene acetals. The process avoids cryogenic conditions, making it more amenable to process-scale use than related methods for β-lactam synthesis. A Gilman-Speeter diastereoselective version using a sulfinyl

  描述了具有TMS亚胺和TMS烯酮缩醛之间直接，未催化的曼尼希反应的高效的Gilman-Speeter合成具有4-芳基取代基的3,4-三取代的β-内酰胺的方法。该方法避免了低温条件，使其比β-内酰胺合成的相关方法更适合于工艺规模使用。还提出了使用亚磺酰基亚胺并导致同手性亚磺酰基β-氨基酯的Gilman-Speeter非对映选择性方案。