diethyl 5,5-dimethyl-2,3-hexadienyl phosphate | 432049-73-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: diethyl 5,5-dimethyl-2,3-hexadienyl phosphate
• CAS: 432049-73-5
• 化学式: C₁₂H₂₃O₄P
• 分子量: 262.286
• InChiKey: VEVDBJLMMNWCHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  双(叔丁氧羰基)胺 、 diethyl 5,5-dimethyl-2,3-hexadienyl phosphate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 (S)-(-)-5,5-双(二苯膦基)-4,4-双-1,3-苯并间二氧杂环戊烯 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以77%的产率得到N,N-di(tert-butoxycarbonyl)-5,5-dimethyl-2,3-hexadienylamine
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric Amination and Imidation of 2,3-Allenyl Phosphates

  摘要：

  [GRAPHICS]Asymmetric amination of 2,3-allenyl phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and imides can be performed efficiently using a combination of zerovalent palladium complexes and SEGPHOS or MeOBlPHEP ligand, affording the corresponding optically active 1-aminated derivatives with enantiomeric excess of up to 97% ee.

  DOI：

  10.1021/ol0523502
• 作为产物：
  描述：

  4-methoxy-5,5-dimethyl-2-hexyn-1-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 diethyl 5,5-dimethyl-2,3-hexadienyl phosphate
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric Amination and Imidation of 2,3-Allenyl Phosphates

  摘要：

  [GRAPHICS]Asymmetric amination of 2,3-allenyl phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and imides can be performed efficiently using a combination of zerovalent palladium complexes and SEGPHOS or MeOBlPHEP ligand, affording the corresponding optically active 1-aminated derivatives with enantiomeric excess of up to 97% ee.

  DOI：

  10.1021/ol0523502

文献信息

• Palladium-Catalyzed Asymmetric Alkylation of 2,3-Alkadienyl Phosphates. Synthesis of Optically Active 2-(2,3-Alkadienyl)malonates
  作者：Yasushi Imada、Katsuya Ueno、Koji Kutsuwa、Shun-Ichi Murahashi

  DOI：10.1246/cl.2002.140

  日期：2002.2

  Asymmetric alkylation of 2,3-alkadienyl phosphates with soft carbon nucleophiles proceeds efficiently in the presence of palladium complex catalyst bearing MeOBIPHEP or BINAP ligand to give optically active functionalized allenes up to 90% ee.

  在带有 MeOBIPHEP 或 BINAP 配体的钯配合物催化剂存在下，2,3-链二烯基磷酸酯与软碳亲核试剂的不对称烷基化可有效进行，得到高达 90% ee 的旋光功能化丙二烯。
• Sequential asymmetric homoallenylation of primary amines with a palladium catalyst
  作者：Yasushi Imada、Masayuki Nishida、Takeshi Naota

  DOI：10.1016/j.tetlet.2008.05.144

  日期：2008.8

  Optically active bis(homoallenyl)amines bearing two chiral axes with the same sense of axial chirality were prepared by a one-pot, palladium-catalyzed sequential homoallenylation of primary amines with 2,3-allenyl phosphates. (C) 2008 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Asymmetric Amination and Imidation of 2,3-Allenyl Phosphates
  作者：Yasushi Imada、Masayuki Nishida、Koji Kutsuwa、Shun-Ichi Murahashi、Takeshi Naota

  DOI：10.1021/ol0523502

  日期：2005.12.1

  [GRAPHICS]Asymmetric amination of 2,3-allenyl phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and imides can be performed efficiently using a combination of zerovalent palladium complexes and SEGPHOS or MeOBlPHEP ligand, affording the corresponding optically active 1-aminated derivatives with enantiomeric excess of up to 97% ee.