(S,E)-N-(2-bromo-5-methoxybenzylidene)-tert-butanesulfinamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S,E)-N-(2-bromo-5-methoxybenzylidene)-tert-butanesulfinamide
• 英文别名: (NE,S)-N-[(2-bromo-5-methoxyphenyl)methylidene]-2-methylpropane-2-sulfinamide
• 化学式: C₁₂H₁₆BrNO₂S
• 分子量: 318.235
• InChiKey: NNGSOELTXAFLDB-AAKUMTKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (S,E)-N-(2-bromo-5-methoxybenzylidene)-tert-butanesulfinamide 在 盐酸 、 copper(l) chloride 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 5.33h， 生成 ethyl (3R)-3-amino-3-(2-bromo-5-methoxyphenyl)propanoate;hydrochloride
  参考文献：
  名称：

  Design, Structure–Activity Relationship, and in Vivo Characterization of the Development Candidate NVP-HSP990

  摘要：

  Utilizing structure-based drug design, a novel dihydropyridopyrimidinone series which exhibited potent Hsp90 inhibition, good pharmacokinetics upon oral administration, and an excellent pharmacokinetic/pharmacodynamic relationship in vivo was developed from a commercial hit. The exploration of this series led to the selection of NVP-HSP990 as a development candidate.

  DOI：

  10.1021/jm501107q
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲醛 、 S-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以98%的产率得到(S,E)-N-(2-bromo-5-methoxybenzylidene)-tert-butanesulfinamide
  参考文献：
  名称：

  来自邻溴芳基醛和酮的手性胺化α-亚甲基苯并环烯烃

  摘要：

  作者感谢西班牙国家科学与创新部长 (MICINN)（授权号 CTQ2007-65218）、Consolider Ingenio（授权号 2010-CSD-2007-00006 和 CTQ2011-24165）、Generalitat Valenciana（授权号为039)、Fondos Europeos para el Desarrollo Regional (FEDER) 和阿利坎特大学的财政支持。

  DOI：

  10.1002/ejoc.201201712

文献信息

• Chiral Aminated α-Methylenebenzocycloalkenes from<i>o</i>-Bromoaryl Aldehydes and Ketones
  作者：Juan Alberto Sirvent、Francisco Foubelo、Miguel Yus

  DOI：10.1002/ejoc.201201712

  日期：2013.4

  The authors thank the Spanish Ministerio de Ciencia e Innovacion (MICINN) (grant number CTQ2007-65218), the Consolider Ingenio (grant numbers 2010-CSD-2007-00006 and CTQ2011-24165), the Generalitat Valenciana (grant number PROMETEO/2009/039), the Fondos Europeos para el Desarrollo Regional (FEDER), and the University of Alicante for the financial support.

  作者感谢西班牙国家科学与创新部长 (MICINN)（授权号 CTQ2007-65218）、Consolider Ingenio（授权号 2010-CSD-2007-00006 和 CTQ2011-24165）、Generalitat Valenciana（授权号为039)、Fondos Europeos para el Desarrollo Regional (FEDER) 和阿利坎特大学的财政支持。
• Design, Structure–Activity Relationship, and in Vivo Characterization of the Development Candidate NVP-HSP990
  作者：Christopher M. McBride、Barry Levine、Yi Xia、Cornelia Bellamacina、Timothy Machajewski、Zhenhai Gao、Paul Renhowe、William Antonios-McCrea、Paul Barsanti、Kristin Brinner、Abran Costales、Brandon Doughan、Xiaodong Lin、Alicia Louie、Maureen McKenna、Kris Mendenhall、Daniel Poon、Alice Rico、Michael Wang、Teresa E. Williams、Tinya Abrams、Susan Fong、Thomas Hendrickson、Dachuan Lei、Julie Lin、Daniel Menezes、Nancy Pryer、Pietro Taverna、Yongjin Xu、Yasheen Zhou、Cynthia M. Shafer

  DOI：10.1021/jm501107q

  日期：2014.11.13

  Utilizing structure-based drug design, a novel dihydropyridopyrimidinone series which exhibited potent Hsp90 inhibition, good pharmacokinetics upon oral administration, and an excellent pharmacokinetic/pharmacodynamic relationship in vivo was developed from a commercial hit. The exploration of this series led to the selection of NVP-HSP990 as a development candidate.
• Asymmetric Vinylogous Aza-Darzens Approach to Vinyl Aziridines
  作者：Isaac Chogii、Pradipta Das、Michael D. Delost、Mark N. Crawford、Jon T. Njardarson

  DOI：10.1021/acs.orglett.8b02074

  日期：2018.8.17

  A new asymmetric approach to assemble cis-vinyl aziridines is reported. A reaction of strategically substituted dienolates, decorated with a gamma-leaving group, with chiral sulfinimines afforded chiral vinyl aziridine products in good to excellent yields. This is the first systematic study toward the realization of a useful asymmetric vinylogous aza-Darzens reaction. The reaction is initiated by a syn-selective addition, affording cis-vinyl aziridine products after displacement of bromide. The low syn-diastereoselectivity is attributed to competing retro-Mannich pathways.