(RS,R)-N-(1-苯基烯丙基)-2-甲基丙基亚磺酰胺 | 1023743-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (RS,R)-N-(1-苯基烯丙基)-2-甲基丙基亚磺酰胺
• 英文名称: (R_S,R)-N-(1-phenylallyl)-2-methylpropylsulfinamide
• 英文别名: (R)-2-methyl-N-[(1R)-1-phenylprop-2-enyl]propane-2-sulfinamide
• CAS: 1023743-85-2
• 化学式: C₁₃H₁₉NOS
• 分子量: 237.366
• InChiKey: SKSRTTVQTCDPIN-MLGOLLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (RS,R)-N-(1-苯基烯丙基)-2-甲基丙基亚磺酰胺 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (R)-N-(1-phenylallyl)benzamide
  参考文献：
  名称：

  N-烯丙基酰胺与三氟甲烷亚磺酸钠的无过渡金属三氟甲基化：含三氟甲基的恶唑啉的合成

  摘要：

  AbstractA transition metal‐free method for the trifluoromethylation of N‐allylamides has been developed, and the corresponding trifluoromethyl‐containing oxazolines were prepared in moderate to good yields. The protocol uses readily available substituted N‐allylamides as the starting materials, inexpensive and easily stored sodium trifluoromethanesulfinate as the trifluoromethyl source, iodobenzene diacetate as the oxidant, and the procedure involves sequential intermolecular trifluoromethylation of alkenes with sodium trifluoromethanesulfinate and intramolecular cyclization. This is the first example to prepare CF3‐containing oxazolines. Therefore, the present method should afford an efficient and practical strategy for synthesis of other CF3‐containing cyclic compounds.magnified image

  DOI：

  10.1002/adsc.201400144
• 作为产物：
  描述：

  苯甲醛 在 Dimethylzinc 、 4-甲基苯磺酸吡啶 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (RS,R)-N-(1-苯基烯丙基)-2-甲基丙基亚磺酰胺
  参考文献：
  名称：

  N-烯丙基酰胺与三氟甲烷亚磺酸钠的无过渡金属三氟甲基化：含三氟甲基的恶唑啉的合成

  摘要：

  AbstractA transition metal‐free method for the trifluoromethylation of N‐allylamides has been developed, and the corresponding trifluoromethyl‐containing oxazolines were prepared in moderate to good yields. The protocol uses readily available substituted N‐allylamides as the starting materials, inexpensive and easily stored sodium trifluoromethanesulfinate as the trifluoromethyl source, iodobenzene diacetate as the oxidant, and the procedure involves sequential intermolecular trifluoromethylation of alkenes with sodium trifluoromethanesulfinate and intramolecular cyclization. This is the first example to prepare CF3‐containing oxazolines. Therefore, the present method should afford an efficient and practical strategy for synthesis of other CF3‐containing cyclic compounds.magnified image

  DOI：

  10.1002/adsc.201400144

文献信息

• Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
  作者：Raquel Almansa、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2008.10.012

  日期：2008.11

  different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to use it as a non-transferable one. Both aromatic and aliphatic aldimines, as well as activated ketimines, are good

  三有机锌酸酯与（R）-N-（叔丁烷亚磺酰基）亚胺的反应以良好或优异的产率得到了预期的α-支化的亚磺酰胺，非对映体比率高达98：2。该ñ产物的-亚磺酰基可通过酸处理容易地除去，从而以高达96％的对映体过量提供相应的手性伯胺。由三有机锌酸盐显示的反应性和选择性不同于用相应的格氏试剂观察到的反应性和选择性，这在某些情况下允许从相同的亚胺底物制备胺的两种对映异构体。当使用混合的三有机锌酸酯时，可以利用甲基的缓慢转移速率将其用作不可转移的甲基。芳族和脂族亚胺以及活化的酮亚胺都是这些加成反应的良好底物。
• Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines
  作者：Derek A. Cogan、Guangcheng Liu、Jonathan Ellman

  DOI：10.1016/s0040-4020(99)00451-2

  日期：1999.7

  High yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert-butanesulfinyl ketimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6)

  对于有机金属试剂的1,2-增补高产量和高立体选择性的方法ñ -叔-butanesulfinyl醛亚胺（2）和Ñ -叔-butanesulfinyl酮亚胺（3）中描述。已证明将烷基，芳基，烯基和烯丙基碳负离子添加到具有不同空间和电子特性的各种亚胺中。亚磺酰胺产物（4和6）的酸性甲醇分解可提供高度对映体富集的α-支化和α，α-二支化胺。由于很容易从醛和酮中获得广泛的亚磺酰基亚胺，因此可以制备多种对映体富集的胺。
• An improved procedure for the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines: use of catalytic dialkylzinc
  作者：Raquel Almansa、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetlet.2009.01.136

  日期：2009.7

  has been performed with very good results by using a catalytic amount of Me2Zn (0.15 equiv) to generate the organozincate. Yields and/or diastereoselectivities of the formed α-branched sulfinamides improve in comparison with the values obtained in the same reactions carried out with an excess of a previously formed triorganozincate. On the other hand, the transfer of the two alkyl groups of a dialkylzinc

  通过使用催化量的Me 2 Zn（0.15当量）产生有机锌酸盐，已经将三有机锌酸盐添加到（R）-N-（叔丁烷亚磺酰基）苯并二胺中，具有非常好的结果。与在过量的先前形成的三有机锌酸酯进行的相同反应中获得的值相比，所形成的α-支化亚磺酰胺的产率和/或非对映选择性提高。另一方面，通过使用0.5当量的二烷基锌和1.5当量的MeMgBr生成三烷基锌酸酯，已经实现了二烷基锌试剂的两个烷基向亚胺的转移。在这两种方法中，均获得了良好的优异收率和非对映异构体比率（高达98：2）。
• Application of the addition of triorganozincates to N-(tert-butanesulfinyl)imines to the enantioselective synthesis of α-amino acids
  作者：Raquel Almansa、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetlet.2009.05.008

  日期：2009.7

  Highly enantiomerically enriched N-protected α-amino acids can be easily prepared from optically pure N-(tert-butanesulfinyl)imines by a four-step sequence involving: diastereoselective addition of a triorganozincate to the imine, removal of the sulfinyl group, benzoylation of the nitrogen atom of the obtained primary amine and oxidation of one of the substituents on the carbon atom α to the nitrogen

  高度对映体富集的N-保护的α-氨基酸可以很容易地由光学纯的N-（叔丁烷亚磺酰基）亚胺通过以下四个步骤序列制得：非对映选择性地向亚胺中添加三有机锌，亚磺酰基的去除，苯甲酰基的苯甲酰化获得的伯胺的氮原子被碳原子α上的取代基之一氧化成氮。在亚磺酰基手性助剂中使用相同的配置，具有（R）或（S可以通过选择亚胺和有机锌酸盐的适当组合来制备构型。具有高光学纯度的α，α-二取代的α-氨基酯也可以通过将三烷基锌酸酯非对映选择性地加成到α-亚氨基酯中来制备。
• Simple <i>N</i>-Sulfinyl-Based Chiral Sulfur–Olefin Ligands for Rhodium-Catalyzed Asymmetric 1,4-Additions
  作者：Xiangqing Feng、Yazhou Wang、Beibei Wei、Jing Yang、Haifeng Du

  DOI：10.1021/ol2009494

  日期：2011.7.1

  A variety of N-sulfinyl-based chiral sulfur-olefin ligands has been successfully developed for the first time for rhodium-catalyzed highly efficient and enantioselective 1,4-additions. The ease of synthesis and needless consideration of the carbon chirality makes this novel type of ligands attractive for asymmetric catalysis.