2-Methyl-propane-2-sulfinic acid (R)-dec-(E)-ylideneamide | 736946-94-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: 2-Methyl-propane-2-sulfinic acid (R)-dec-(E)-ylideneamide
• 英文别名: (NE,R)-N-decylidene-2-methylpropane-2-sulfinamide
• CAS: 736946-94-4
• 化学式: C₁₄H₂₉NOS
• 分子量: 259.456
• InChiKey: RFGCYTQKSNKQSW-LCJXNMAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-Methyl-propane-2-sulfinic acid (R)-dec-(E)-ylideneamide 在 palladium diacetate 、 双(2-二苯基磷苯基)醚 咪唑 、 盐酸 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 copper bromide dimethyl sulfide complex 、 臭氧 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.0h， 生成 [(2S,3S,5R)-2-benzyl-1-methyl-5-nonylpyrrolidin-3-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  A Concise Stereoselective Synthesis of Preussin, 3-epi-Preussin, and Analogues

  摘要：

  A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.

  DOI：

  10.1021/ol0606435
• 作为产物：
  描述：

  癸醛 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到2-Methyl-propane-2-sulfinic acid (R)-dec-(E)-ylideneamide
  参考文献：
  名称：

  A Concise Stereoselective Synthesis of Preussin, 3-epi-Preussin, and Analogues

  摘要：

  A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1'-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.

  DOI：

  10.1021/ol0606435

文献信息

• Stereoselective Coupling of <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines and β-Keto Acids: Access to β-Amino Ketones
  作者：Alejandro Lahosa、Tatiana Soler、Ana Arrieta、Fernando P. Cossío、Francisco Foubelo、Miguel Yus

  DOI：10.1021/acs.joc.7b01178

  日期：2017.7.21

  The reaction of chiral N-tert-butanesulfinyl aldimines with beta-keto acids under basic conditions at room temperature proceeds with high levels of diastereocontrol, leading to beta-amino ketones in high yields. Based on DFT calculations, an eight-membered cyclic transition state involving coordination of the lithium atom to the oxygens of carboxylate and sulfinyl units was proposed, being in agreement with the observed experimental diastereomeric ratios. The synthesis of the piperidine alkaloid (-)-pelletierine was successfully undertaken in order to demonstrate the utility of this methodology.
• A Convenient Synthesis of Chiral Nonracemic Vinyl Aziridines
  作者：Daniel Morton、David Pearson、Robert A. Field、Robert A. Stockman

  DOI：10.1021/ol049252l

  日期：2004.7.1

  The preparation of a range of alkyl and aryl chiral vinyl aziridines was achieved in high yield and stereoselectivity, and with excellent diastereoselectivity, by reaction of tert-butylsulfinylimines with the ylide derived from S-allyl tetrahydrothiophenium bromide.