(R)-diethyl 1-(1-hydroxy-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate | 1215035-94-1

• 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: (R)-diethyl 1-(1-hydroxy-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate
• 英文别名: diethyl 1-(1-hydroxy-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate；ethyl N-(ethoxycarbonylamino)-N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamate
• CAS: 1215035-94-1
• 化学式: C₁₅H₂₂N₂O₅
• 分子量: 310.35
• InChiKey: SQSLSDMMLUQZDD-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 (R)-diethyl 1-(1-hydroxy-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  咪唑鎓离子标记的脯氨酸有机催化剂催化的离子液体中醛与偶氮二羧酸的直接不对称α-胺化反应

  摘要：

  在咪唑鎓离子标记的1-脯氨酸有机催化剂1存在下，离子液体中的未改性醛与偶氮二羧酸酯的直接不对称α胺化反应具有出色的对映选择性（高达98％ee）和高化学产率。该系统可以轻松地回收和再利用至少四次，而不会显着损失产率和对映选择性。

  DOI：

  10.1016/j.tetlet.2010.09.036

文献信息

• Remarkable Reaction Rate and Excellent Enantioselective Direct α-Amination of Aldehydes with Azodicarboxylates Catalyzed by Pyrrolidinylcamphor-Derived Organocatalysts
  作者：Pang-Min Liu、Chihliang Chang、Raju Jannapu Reddy、Ying-Fang Ting、Hsuan-Hao Kuan、Kwunmin Chen

  DOI：10.1002/ejoc.200901151

  日期：2010.1

  Remarkable reaction rate and excellent enantioselective direct α-amination of unmodified aldehydes with various azodicarboxylates was catalyzed by pyrrolidinylcamphor organo-catalyst 2a (5 mol-%) to provide the desired aminated products with excellent chemical yields and high to excellent levels of enantioselectivity (up to >99%ee) at 0 °C in CH 2 Cl 2 .

  由吡咯烷基樟脑有机催化剂 2a (5 mol-%) 催化未改性醛与各种偶氮二羧酸酯的显着反应速率和优异的对映选择性直接 α-胺化，以提供所需的胺化产物，具有优异的化学产率和高至优异的对映选择性水平（高达>99%ee) 在 0 °C 的 CH 2 Cl 2 中。
• C–C bond fragmentation by Grob/Eschenmoser reactions, applications in dendrimer synthesis
  作者：Judith Hierold、David W. Lupton

  DOI：10.1039/c3ob40800k

  日期：——

  C–C bond fragmentation of structurally diverse carbocycles has been applied to the divergent synthesis of dendrimers. The fragmentation has been paired to deprotection or thio-Michael reaction, allowing the preparation of a fourth generation dendrimer of narrow molecular weight distribution. Methodologies to increase water solubility have been examined using appended carboxylic acid or oligoether moieties

  结构多样的碳环的C–C键断裂已应用于树枝状聚合物的多样化合成中。该片段已与去保护或硫代迈克尔反应配对，从而可制备分子量分布窄的第四代树状聚合物。增加方法水已经使用附加的羧酸或低聚醚部分检查了溶解度。另外，手性脯氨醇衍生物的掺入导致树枝状大分子的合成，已显示其以良好的产率和适度的对映选择性催化醛的α-胺化。
• Highly effective and enantioselective α-amination of aldehydes promoted by chiral proline amide–thiourea bifunctional catalysts
  作者：Ji-Ya Fu、Qing-Chun Huang、Qiao-Wei Wang、Li-Xin Wang、Xiao-Ying Xu

  DOI：10.1016/j.tetlet.2010.07.042

  日期：2010.9

  A series of secondary amine–thiourea catalysts derived from l-proline and chiral diamine were prepared and successfully applied to the highly effective and enantioselective α-amination of unmodified aldehydes with various azodicarboxylates in excellent yields (up to 99%) and enantioselectivities (up to 99% ee) within a few minutes.

  制备了一系列衍生自l-脯氨酸和手性二胺的仲胺-硫脲催化剂，并成功地用于未改性醛与各种偶氮二羧酸酯的高效和对映选择性α-氨基化反应，具有极好的收率（高达99％）和对映选择性（高达几分钟内即可获得99％ee）。
• Polymer-immobilized α,α-bis[bis-3,5-(trifluoromethyl)phenyl]prolinol silyl ether: synthesis and application in the asymmetric α-amination of aldehydes
  作者：Anton A. Guryev、Maksim V. Anokhin、Alexei D. Averin、Irina P. Beletskaya

  DOI：10.1016/j.mencom.2015.11.002

  日期：2015.11

  alpha,alpha-Bis[bis-3,5-(trifluoromethyl)phenyl]prolinol silyl ether anchored onto polystyrene was synthesized and tested in asymmetric alpha-amination of aldehydes. The catalytic activity and enantioselectivity of the immobilized catalyst persist for 3 cycles.
• Synthesis and use of a stable aminal derived from TsDPEN in asymmetric organocatalysis
  作者：Silvia Gosiewska、Rina Soni、Guy J. Clarkson、Martin Wills

  DOI：10.1016/j.tetlet.2010.06.017

  日期：2010.8

  A stable aminal formed stereoselectively from (R,R)-N-tosyl-1,2-diphenyl-1,2-ethylenediamine (TsDPEN) is capable of asymmetric organocatalysis of Diels-Alder and alpha-amination reactions of aldehydes. (C) 2010 Elsevier Ltd. All rights reserved.