(3R,4R)-1-phenyl-3,4-diaminopyrrolidine | 880497-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,4R)-1-phenyl-3,4-diaminopyrrolidine
• 英文别名: (3R,4R)-3,4-diamino-1-phenylpyrrolidine；(3R,4R)-1-phenylpyrrolidine-3,4-diamine
• CAS: 880497-74-5
• 化学式: C₁₀H₁₅N₃
• 分子量: 177.249
• InChiKey: OKBPWKDYRUWVKA-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-phenyl-3,4-diaminopyrrolidine 、 2-羟基-1-萘甲醛 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以68%的产率得到1-[[(3R,4R)-4-[(2-hydroxynaphthalen-1-yl)methylideneamino]-1-phenylpyrrolidin-3-yl]iminomethyl]naphthalen-2-ol
  参考文献：
  名称：

  The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3,4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes

  摘要：

  The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural L-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.015
• 作为产物：
  描述：

  (3R,4R)-1-phenyl-3,4-dihydroxy-2,5-dioxopyrrolidine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (3R,4R)-1-phenyl-3,4-diaminopyrrolidine
  参考文献：
  名称：

  The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3,4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes

  摘要：

  The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural L-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.015

文献信息

• Syntheses of Enantiopure 3,4-Diamino-1-Substituted Pyrrolidines
  作者：Charles M. Marson、Robert C. Melling

  DOI：10.1055/s-2005-924769

  日期：——

  A convenient and general route to enantiopure 3,4-diamino-1-substituted pyrrolidines has been devised. 1-Alkyl, 1-alkanoyl, 1-cycloalkyl and 1-aryl-3,4-diaminopyrrolidines of the (3R,4R)-configurations have all been prepared, the cycloalkyl and (mono)aryl being novel derivatives. A previous difficulty in the synthesis of such compounds is the observation that dimesylates undergo two-fold displacement with sodium azide in very poor yields (<10%), if at all. However, use of lithium azide permits satisfactory yields of the diazides 5 and hence the corresponding diamines 6 and their derivatives, and avoids the generation and use of hydrazoic acid, as previously required in a Mitsunobu procedure.

  我们设计出了一种获得对映体纯度为 3,4-二氨基-1-取代吡咯烷的简便而通用的方法。1-烷基、1-烷酰基、1-环烷基和 1-芳基-3,4-二氨基吡咯烷的 (3R,4R)-构型均已制备完成，其中环烷基和（单）芳基为新型衍生物。以前合成此类化合物的一个难点是观察到二甲基酸盐在叠氮化钠的作用下发生两次置换，即使发生置换，产率也非常低（小于 10%）。不过，使用叠氮化锂可以获得令人满意的重氮化物 5 收率，从而得到相应的二胺 6 及其衍生物，并避免了以前在 Mitsunobu 程序中需要生成和使用的安息香酸。
• The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3,4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes
  作者：M. Elisa Silva Serra、Dina Murtinho、Albertino Goth

  DOI：10.1016/j.tetasy.2013.01.015

  日期：2013.3

  The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural L-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine. (C) 2013 Elsevier Ltd. All rights reserved.