(S)-2-(2,3-bis(diisopropylamino)cycloallylamino)-3-phenylpropan-1-ol | 1366421-77-3

• 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: (S)-2-(2,3-bis(diisopropylamino)cycloallylamino)-3-phenylpropan-1-ol
• 英文别名: (2S)-2-[[2,3-bis[di(propan-2-yl)amino]cycloprop-2-en-1-ylidene]amino]-3-phenylpropan-1-ol
• CAS: 1366421-77-3
• 化学式: C₂₄H₃₉N₃O
• 分子量: 385.593
• InChiKey: QMWNERZXHSNYSB-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-2-(2,3-bis(diisopropylamino)cycloallylamino)-3-phenylpropan-1-ol hydrochloride 在 sodium hydride 作用下， 以 乙腈 、 正戊烷 为溶剂， 反应 0.25h， 以55%的产率得到(S)-2-(2,3-bis(diisopropylamino)cycloallylamino)-3-phenylpropan-1-ol
  参考文献：
  名称：

  [EN] CYCLOPROPENIMINE CATALYST COMPOSITIONS AND PROCESSES
  [FR] COMPOSITIONS CATALYTIQUES À BASE DE CYCLOPROPÉNIMINE ET PROCÉDÉS

  摘要：

  本发明提供了环丙烯亚胺Brønsted碱催化剂和用作Brønsted碱催化剂的环丙烯亚胺骨架，其中该环丙烯亚胺具有结构（100）。还提供了制备这种环丙烯亚胺的方法。此外，还提供了进行有机合成反应的方法以及利用这种环丙烯亚胺Brønsted碱催化剂对质子转移反应进行对映选择性催化的方法。

  公开号：

  WO2013059118A1

文献信息

• Structure–activity relationship studies of cyclopropenimines as enantioselective Brønsted base catalysts
  作者：Jeffrey S. Bandar、Alexandre Barthelme、Alon Y. Mazori、Tristan H. Lambert

  DOI：10.1039/c4sc02402h

  日期：——

  New insights aid in the understanding and design of cyclopropenimine-based asymmetric catalysts.

  新的见解有助于理解和设计基于环丙烯亚胺的不对称催化剂。
• Enantioselective Brønsted Base Catalysis with Chiral Cyclopropenimines
  作者：Jeffrey S. Bandar、Tristan H. Lambert

  DOI：10.1021/ja3015764

  日期：2012.3.28

  Cyclopropenimines are shown to be a highly effective new class of enantioselective Bronsted base catalysts. A chiral 2,3-bis(dialkylamino)cyclopropenimine catalyzes the rapid Michael reaction of a glycine imine substrate with high levels of enantioselectivity. A preparative scale reaction to deliver 25 g of product is demonstrated, and a trivial large scale synthesis of the optimal catalyst is shown. In addition, the basicity of a 2,3-bis(dialkylamino)cyclopropenimine is measured for the first time and shown to be approximately equivalent to the P-1-tBu phosphazene base. An X-ray crystal structure of the protonated catalyst is shown along with a proposed mechanistic and stereochemical rationale.
• CYCLOPROPENIMINE CATALYST COMPOSITIONS AND PROCESSES
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20140288323A1

  公开（公告）日：2014-09-25

  The present invention provides, inter alia, a cyclopropenimine Brønsted base catalyst and a cyclopropenimine scaffold for use as a Brønsted base catalyst. This cyclopropenimine has the structure (100). Methods for making such a cyclopropenimine are also provided. Further provided are processes for carrying out an organic synthetic reaction and processes for catalyzing a proton transfer reaction enantioselectively using such a cyclopropenimine Brønsted base catalyst.