3-(dibenzylamino)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate | 144728-78-9

• 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-(dibenzylamino)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate
• 英文别名: 3-(N,N-Dibenzylamino)propyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate；3-(Dibenzylamino)propyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS: 144728-78-9
• 化学式: C₂₅H₃₄N₂O₃
• 分子量: 410.557
• InChiKey: FPVBDHXCFUAVRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(dibenzylamino)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate 、 对溴甲苯 在 仲丁基锂 、 鹰爪豆碱 、 zinc diacetate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 以71%的产率得到(R)-(+)-3-(dibenzylamino)-1-(p-tolyl)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Enantioselective α-Arylation of O-Carbamates via Sparteine-Mediated Lithiation and Negishi Cross-Coupling

  摘要：

  A general and enantioselective arylation of carbamates derived from primary alcohols was developed by combining Hoppe's sparteine-mediated asymmetric lithiation with Negishi cross-coupling. Coupled with Aggarwal's lithiation-borylation sequence, the current method provides a short and divergent access to a variety of enantioenriched secondary and tertiary benzylic alcohols.

  DOI：

  10.1021/acs.orglett.6b03472
• 作为产物：
  描述：

  2,2,4,4-四甲基-1,3-恶唑烷 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 mineral oil 、 苯 为溶剂， 反应 32.5h， 生成 3-(dibenzylamino)propyl 2,2,4,4-tetramethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Enantioselective α-Arylation of O-Carbamates via Sparteine-Mediated Lithiation and Negishi Cross-Coupling

  摘要：

  A general and enantioselective arylation of carbamates derived from primary alcohols was developed by combining Hoppe's sparteine-mediated asymmetric lithiation with Negishi cross-coupling. Coupled with Aggarwal's lithiation-borylation sequence, the current method provides a short and divergent access to a variety of enantioenriched secondary and tertiary benzylic alcohols.

  DOI：

  10.1021/acs.orglett.6b03472

文献信息

• US5223633A
  申请人：——

  公开号：US5223633A

  公开（公告）日：1993-06-29
• Enantioselective α-Arylation of <i>O</i>-Carbamates via Sparteine-Mediated Lithiation and Negishi Cross-Coupling
  作者：Titouan Royal、Yann Baumgartner、Olivier Baudoin

  DOI：10.1021/acs.orglett.6b03472

  日期：2017.1.6

  A general and enantioselective arylation of carbamates derived from primary alcohols was developed by combining Hoppe's sparteine-mediated asymmetric lithiation with Negishi cross-coupling. Coupled with Aggarwal's lithiation-borylation sequence, the current method provides a short and divergent access to a variety of enantioenriched secondary and tertiary benzylic alcohols.