3-(benzylamino)-2-methyl-3-phenyl-2-((trimethylsilyl)methyl)propan-1-ol | 1198587-76-6

• 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: 3-(benzylamino)-2-methyl-3-phenyl-2-((trimethylsilyl)methyl)propan-1-ol
• 英文别名: DY-1-143B；3-(Benzylamino)-2-methyl-3-phenyl-2-(trimethylsilylmethyl)propan-1-ol；3-(benzylamino)-2-methyl-3-phenyl-2-(trimethylsilylmethyl)propan-1-ol
• CAS: 1198587-76-6
• 化学式: C₂₁H₃₁NOSi
• 分子量: 341.569
• InChiKey: GVEVGDAUSBPRTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(benzylamino)-2-methyl-3-phenyl-2-((trimethylsilyl)methyl)propan-1-ol 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以70%的产率得到(3S,4S,9aS)-3-methyl-4-phenyl-3-((trimethylsilyl)methyl)octahydropyrido[2,1-b][1,3]oxazine
  参考文献：
  名称：

  Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions

  摘要：

  Regioselective titanium alkoxide-mediated reductive cross-coupling reactions of allylic alcohols with vinylsilanes and imines have previously been demonstrated to proceed with allylic transposition by formal metallo-[3,3]-rearrangement [thought to proceed by a sequence of: (1) directed carbometalation, and (2) syn-elimination]. While many examples have been described that support this reaction path, a collection of substrates have recently been identified that react by way of an alternative pathway, delivering a concise convergent route to coupled products bearing a quaternary center. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.059
• 作为产物：
  描述：

  、 N-苄烯丁胺 在 titanium(IV) isopropylate 、 Cyclopentylmagnesium chloride 作用下， 以 乙醚 、 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以75%的产率得到3-(benzylamino)-2-methyl-3-phenyl-2-((trimethylsilyl)methyl)propan-1-ol
  参考文献：
  名称：

  A Convergent Stereoselective Synthesis of Quinolizidines and Indolizidines: Chemoselective Coupling of 2-Hydroxymethyl-Substituted Allylic Silanes with Imines

  摘要：

  A convergent synthesis of stereodefined indolizidines and quinolizidines through chemoselective allyl transfer between 2-hydroxymethyl-substituted allylic silanes and imines is described. Overall, highly substituted heterocycles that contain three stereogenic centers and up to four fused rings can be accessed in two steps from relatively simple coupling partners.

  DOI：

  10.1021/ja908504z

文献信息

• Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions
  作者：Dexi Yang、Justin K. Belardi、Glenn C. Micalizio

  DOI：10.1016/j.tetlet.2010.11.059

  日期：2011.4

  Regioselective titanium alkoxide-mediated reductive cross-coupling reactions of allylic alcohols with vinylsilanes and imines have previously been demonstrated to proceed with allylic transposition by formal metallo-[3,3]-rearrangement [thought to proceed by a sequence of: (1) directed carbometalation, and (2) syn-elimination]. While many examples have been described that support this reaction path, a collection of substrates have recently been identified that react by way of an alternative pathway, delivering a concise convergent route to coupled products bearing a quaternary center. (C) 2010 Elsevier Ltd. All rights reserved.
• A Convergent Stereoselective Synthesis of Quinolizidines and Indolizidines: Chemoselective Coupling of 2-Hydroxymethyl-Substituted Allylic Silanes with Imines
  作者：Dexi Yang、Glenn C. Micalizio

  DOI：10.1021/ja908504z

  日期：2009.12.9

  A convergent synthesis of stereodefined indolizidines and quinolizidines through chemoselective allyl transfer between 2-hydroxymethyl-substituted allylic silanes and imines is described. Overall, highly substituted heterocycles that contain three stereogenic centers and up to four fused rings can be accessed in two steps from relatively simple coupling partners.