(E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)-2,4,6-triisopropylbenzenesulfonohydrazide | 1448295-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)-2,4,6-triisopropylbenzenesulfonohydrazide
• 英文别名: N-[(E)-3,4-dihydro-2H-naphthalen-1-ylideneamino]-2,4,6-tri(propan-2-yl)benzenesulfonamide
• CAS: 1448295-56-4
• 化学式: C₂₅H₃₄N₂O₂S
• 分子量: 426.623
• InChiKey: IFBWCAMHOOZBTL-SHHOIMCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)-2,4,6-triisopropylbenzenesulfonohydrazide 在 正丁基锂 、 氟双(苯基磺酰基)甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 以50%的产率得到4-氟-1,2-二氢萘
  参考文献：
  名称：

  Preparation of Fluoroalkenes via the Shapiro Reaction: Direct Access to Fluorinated Peptidomimetics

  摘要：

  Fluoroalkenes represent a useful class of peptidomimetics with distinct biophysical properties. Current preparations of this functional group commonly provide mixtures of E- or Z-fluoroalkene diastereomers, and/or mixtures of nonfluorinated products. To directly access fluoroalkenes in good stereoselectivity, a Shapiro fluorination reaction was developed. Fluoroalkene products were accessed in one- or two-step sequences from widely available ketones. This strategy should be useful for the preparation of fluorinated analogs of peptide-based therapeutics, many of which would be challenging to prepare by alternate strategies.

  DOI：

  10.1021/ol401637n
• 作为产物：
  描述：

  2,4,6-三异丙基苯磺酰氯 在 肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 (E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)-2,4,6-triisopropylbenzenesulfonohydrazide
  参考文献：
  名称：

  Preparation of Fluoroalkenes via the Shapiro Reaction: Direct Access to Fluorinated Peptidomimetics

  摘要：

  Fluoroalkenes represent a useful class of peptidomimetics with distinct biophysical properties. Current preparations of this functional group commonly provide mixtures of E- or Z-fluoroalkene diastereomers, and/or mixtures of nonfluorinated products. To directly access fluoroalkenes in good stereoselectivity, a Shapiro fluorination reaction was developed. Fluoroalkene products were accessed in one- or two-step sequences from widely available ketones. This strategy should be useful for the preparation of fluorinated analogs of peptide-based therapeutics, many of which would be challenging to prepare by alternate strategies.

  DOI：

  10.1021/ol401637n

文献信息

• MISLANKAR, D. G.;MUGRAGE, B.;DARLING, S. D., TETRAHEDRON LETT., 1981, 22, N 22, 4619-4622
  作者：MISLANKAR, D. G.、MUGRAGE, B.、DARLING, S. D.

  DOI：——

  日期：——
• JONES, T. K.;DENMARK, S. E., HELV. CHIM. ACTA, 1983, 66, N 8, 2377-2396
  作者：JONES, T. K.、DENMARK, S. E.

  DOI：——

  日期：——