N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-2-methylpropanediamide | 644994-49-0

• 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: N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-2-methylpropanediamide
• CAS: 644994-49-0
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: JVFXZSKCMPQOPO-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-2-methylpropanediamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以65%的产率得到(4R,4’R)-2,2’-ethylidenebis[4,5-dihydro-4-phenyloxazole]
  参考文献：
  名称：

  Reusable nano-sized chiral bisoxazoline catalysts

  摘要：

  The nano-sized gold particle-based chiral catalyst having two kinds of alkyl thiol spacers, one of which is substituted with the chiral bisoxazoline/copper(II) complex at the end, behaves as reusable homogeneous catalyst. This gold particle complex acts as nearly homogeneous catalyst in the ene reaction between 2-phenylpropene and ethyl glyoxylate in dichloromethane, while it undergoes dense aggregation when diluted with hexane so as to be separated by simple filtration. Thus, the catalyst can be recovered after the completion of reaction by the repeated sequences of solvent exchange, centrifugal treatment, and decantation, followed by the recharge of substrates, and the situation is ready for the second reaction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.100
• 作为产物：
  描述：

  2-methylmalonyl dichloride 、 D-苯甘氨醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以75%的产率得到N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-2-methylpropanediamide
  参考文献：
  名称：

  Reusable nano-sized chiral bisoxazoline catalysts

  摘要：

  The nano-sized gold particle-based chiral catalyst having two kinds of alkyl thiol spacers, one of which is substituted with the chiral bisoxazoline/copper(II) complex at the end, behaves as reusable homogeneous catalyst. This gold particle complex acts as nearly homogeneous catalyst in the ene reaction between 2-phenylpropene and ethyl glyoxylate in dichloromethane, while it undergoes dense aggregation when diluted with hexane so as to be separated by simple filtration. Thus, the catalyst can be recovered after the completion of reaction by the repeated sequences of solvent exchange, centrifugal treatment, and decantation, followed by the recharge of substrates, and the situation is ready for the second reaction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.100

文献信息

• Modular Synthesis of Chiral Homo- and Heterotrisoxazolines. Improving the Enantioselectivity in the Asymmetric Michael Addition of Indole to Benzylidene Malonate
  作者：Meng-Chun Ye、Bin Li、Jian Zhou、Xiu-Li Sun、Yong Tang

  DOI：10.1021/jo050595m

  日期：2005.7.1

  A simple approach to a diverse set of chiral trisoxazolines is described. Deprotonation of bisoxazolines 2, followed by treatment of 2-chloromethyloxazolines 3, affords chiral trisoxazolines, including chiral homo- and hetero-trisoxazolines in good to high yields. These trisoxazolines are successfully applied in the asymmetric reaction of indole with benzylidene malonate, and ee's up to 93% were obtained.
• Chiral ditopic receptors. Application to palladium-catalyzed allylic alkylation
  作者：Jean Bourguignon、Ulf Bremberg、Georges Dupas、Kristina Hallman、Lars Hagberg、Laurent Hortala、Vincent Levacher、Serghey Lutsenko、Emmanuel Macedo、Christina Moberg、Guy Quéguiner、Fredrik Rahm

  DOI：10.1016/j.tet.2003.10.005

  日期：2003.11

  Chiral pyridinooxazoline, quinolinooxazoline, bis(oxazolino)pyridine (pybox), and bisoxazoline (box) derivatives containing crown ether residues were prepared. Some of the ligands were assessed in substrate binding studies and in palladium catalyzed allylic alkylations. (C) 2003 Elsevier Ltd. All rights reserved.
• Reusable nano-sized chiral bisoxazoline catalysts
  作者：Fumiyasu Ono、Shuji Kanemasa、Junji Tanaka

  DOI：10.1016/j.tetlet.2005.08.100

  日期：2005.10

  The nano-sized gold particle-based chiral catalyst having two kinds of alkyl thiol spacers, one of which is substituted with the chiral bisoxazoline/copper(II) complex at the end, behaves as reusable homogeneous catalyst. This gold particle complex acts as nearly homogeneous catalyst in the ene reaction between 2-phenylpropene and ethyl glyoxylate in dichloromethane, while it undergoes dense aggregation when diluted with hexane so as to be separated by simple filtration. Thus, the catalyst can be recovered after the completion of reaction by the repeated sequences of solvent exchange, centrifugal treatment, and decantation, followed by the recharge of substrates, and the situation is ready for the second reaction. (c) 2005 Elsevier Ltd. All rights reserved.
• Soluble polyisobutylene-supported reusable catalysts for olefin cyclopropanation
  作者：David E. Bergbreiter、Jianhua Tian

  DOI：10.1016/j.tetlet.2007.04.147

  日期：2007.6

  Polyisobutylene oligomers (PIB) have been used as soluble supports for the immobilization of cyclopropanation catalysts. In addition to simple carboxylate ligands, chiral bisoxazolines have been successfully attached to these heptane-soluble polymers. Their use and recovery has been investigated using cyclopropanation of styrene as an example. An achiral PIB-bound Rh(II) catalyst showed good activity and could be easily recycled nine times using a liquid-liquid biphasic separation technique. PIB-supported bisoxazoline ligands for Cu(I) catalysts were also prepared. These chiral catalysts showed good catalytic activity and stereoselectivity. A chiral ligand prepared from phenylglycine provided the most effective stereocontrol and gave the trans- and cis-cyclopropanation products in 94% ee and 68% ee, respectively. All three PIB-bound chiral bisoxazoline-Cu(I) catalysts prepared could be reused five to six times. (c) 2007 Elsevier Ltd. All rights reserved.