(R_S,2S)-2-methyl-propane-2-sulfinic acid (2-benzyloxypropylidene)-amide | 638211-24-2

• 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: (R_S,2S)-2-methyl-propane-2-sulfinic acid (2-benzyloxypropylidene)-amide
• 英文别名: (R_S,E)-N-[(2S)-2-(benzyloxy)propylidene]-2-methyl-2-propanesulfinamide；(NE,R)-2-methyl-N-[(2S)-2-phenylmethoxypropylidene]propane-2-sulfinamide
• CAS: 638211-24-2
• 化学式: C₁₄H₂₁NO₂S
• 分子量: 267.392
• InChiKey: UWNYVRBSNSNKIH-MFFDQAPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R_S,2S)-2-methyl-propane-2-sulfinic acid (2-benzyloxypropylidene)-amide 在 盐酸 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 (1R,2S)-2-Benzyloxy-1-phenyl-propylamine; hydrochloride
  参考文献：
  名称：

  Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines

  摘要：

  N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.

  DOI：

  10.1021/jo035224p
• 作为产物：
  描述：

  (S)-2-苄氧基丙醛 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(R_S,2S)-2-methyl-propane-2-sulfinic acid (2-benzyloxypropylidene)-amide
  参考文献：
  名称：

  与溴二氟乙酸乙酯和α-氧代次磺基嘧啶反应的本田-Reformatsky反应的立体选择性

  摘要：

  描述了溴二氟乙酸乙酯对α-氧化的亚磺酰亚胺的Reformatsky反应。使用Honda-Reformatsky条件，反应会进行双非对映异构化，亚磺酰基的构型决定了反应的立体化学过程。对于匹配的情况，获得了极好的非对映选择性（> 94：6）。相反，与衍生自未取代的链烷烃的亚磺酰亚胺的反应几乎没有非对映选择性。

  DOI：

  10.1021/jo500396p

文献信息

• One-Pot Microwave-Promoted Synthesis of Nitriles from Aldehydes via <i>tert</i>-Butanesulfinyl Imines
  作者：Jonathan Ellman、Jessica Tanuwidjaja、Hillary Peltier、Jared Lewis、Laurie Schenkel

  DOI：10.1055/s-2007-990805

  日期：2007.11

  facile, one-pot method for the synthesis of nitriles from aldehydes via a microwave-promoted, concerted elimination of TERT-butanesulfenic acid from TERT-butanesulfinyl-protected imines-, is described. The mild reaction conditions exhibit broad functional group compatibility and generate products in good isolated yield (69-87%). This method provides a rapid and mild procedure for the synthesis of various

  描述了一种简便的单锅法，通过微波促进、协同消除叔丁亚磺酰基保护的亚胺中的叔丁亚磺酸，从醛中合成腈。温和的反应条件表现出广泛的官能团相容性，并以良好的分离产率 (69-87%) 生成产物。该方法为合成各种官能化腈提供了一种快速而温和的方法。
• Stereoselectivity of the Honda–Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α-Oxygenated Sulfinylimines
  作者：Clément Q. Fontenelle、Matthew Conroy、Mark Light、Thomas Poisson、Xavier Pannecoucke、Bruno Linclau

  DOI：10.1021/jo500396p

  日期：2014.5.2

  The Reformatsky reaction of ethyl bromodifluoroacetate to α-oxygenated sulfinylimines is described. Using Honda–Reformatsky conditions, the reaction proceeds with double diastereodifferentiation, with the configuration of the sulfinyl group determining the stereochemical course of the reaction. Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines

  描述了溴二氟乙酸乙酯对α-氧化的亚磺酰亚胺的Reformatsky反应。使用Honda-Reformatsky条件，反应会进行双非对映异构化，亚磺酰基的构型决定了反应的立体化学过程。对于匹配的情况，获得了极好的非对映选择性（> 94：6）。相反，与衍生自未取代的链烷烃的亚磺酰亚胺的反应几乎没有非对映选择性。
• Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to <i>N</i>-<i>tert</i>-Butanesulfinyl α-Alkoxyaldimines
  作者：Jared W. Evans、Jonathan A. Ellman

  DOI：10.1021/jo035224p

  日期：2003.12.1

  N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.