N-((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)benzamide

• 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-((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)benzamide
• 英文别名: N-[(1S,3R)-3-amino-2,2,3-trimethylcyclopentyl]benzamide
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: WTSFMERTNQLVJE-SWLSCSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)benzamide 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 (1R,3S)-1-N-ethyl-1,2,2-trimethylcyclopentane-1,3-diamine
  参考文献：
  名称：

  Novel tridentate ligands derived from (+)-camphoric acid for enantioselective ethylation of aromatic aldehydes

  摘要：

  Novel tridentate ligands were prepared from (+)-camphoric acid, using simple synthetic sequences. The synthesized ligands were used in enantioselective ethylations of benzaldehydes, showing enantioselectivities up to 92%, at room temperature. Extending the reaction to other aromatic aldehydes, very good results (almost quantitative yields and ee up to 97%, for m-anisaldehyde) were obtained. Structural features such as no substitution in the salicylaldehyde moiety of the Schiff base and an ethyl group in the nitrogen at the Cl position of the cyclopentane ring seem to be essential for obtaining high enantioselectivities. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.09.017
• 作为产物：
  描述：

  D-樟脑酸 在 sodium azide 、 硫酸 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.0h， 生成 N-((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)benzamide
  参考文献：
  名称：

  Synthesis and catalytic activity of new chiral ligands based on a 1,3-cyclopentanediamine

  摘要：

  (1R,3S)-1,2,2-三甲基-1,3-环戊烷二胺及其衍生物已被制备并用作手性配体，用于有机金属化合物与醛之间的不对称加成反应。

  DOI：

  10.1016/s0957-4166(00)82302-2

文献信息

• Synthesis and catalytic activity of new chiral ligands based on a 1,3-cyclopentanediamine
  作者：Hirokazu Urabe、Tetsuro Yamakawa、Fumie Sato

  DOI：10.1016/s0957-4166(00)82302-2

  日期：1992.1

  (1R,3S)-1,2,2-Trimethyl-1,3-cyclopentanediamine and its derivatives have been prepared and utilized as chiral ligands for asymmetric addition reactions of organometallics to aldehydes.

  (1R,3S)-1,2,2-三甲基-1,3-环戊烷二胺及其衍生物已被制备并用作手性配体，用于有机金属化合物与醛之间的不对称加成反应。
• Reactivity of Copper(I) Complexes Containing Ligands Derived from (1 <i>S</i> ,3 <i>R</i> )‐Camphoric Acid with Dioxygen
  作者：Fabian Stöhr、Niclas Kulhanek、Jonathan Becker、Richard Göttlich、Siegfried Schindler

  DOI：10.1002/ejic.202100187

  日期：2021.6.14

  derivatives prepared from camphoric acid were used as ligands for the synthesis of corresponding copper(I) complexes. Their reactivity towards dioxygen was analyzed. The formation of a short-lived bis(μ-oxido)copper complex was spectroscopically observed during the reaction of the copper(I) complex with (1R, 3S)-N1,N1,N3,N3-Tetramethyl-1,2,2-trimethylcyclopentane-1,3-diamine as a ligand. Furthermore, a

  由樟脑酸制备的胺衍生物用作合成相应铜 (I) 配合物的配体。分析了它们对双氧的反应性。在铜 (I) 配合物与 (1 R , 3 S )- N 1 , N 1 , N 3 , N 3反应期间，通过光谱观察到短寿命双（μ-氧化）铜配合物的形成-四甲基-1,2,2-三甲基环戊烷-1,3-二胺作为配体。此外，检测到配体系统的区域选择性去甲基化。配体甲基的氘化允许双（μ-氧化）铜配合物的结晶和表征。带有吡啶残基的配体衍生物会抑制相应的铜 (I) 配合物对分子氧的反应性。此外，可以对配体系统进行修饰，以用于与苯甲醛的分子内氧化反应，导致形成水杨醛，邻位选择性羟基化。
• Reactivity of Copper Complexes with Tripodal Tetradentate Ligands based on Camphoric Acid towards Dioxygen
  作者：Fabian Stöhr、Pascal Specht、Jonathan Becker、Richard Göttlich、Siegfried Schindler

  DOI：10.1002/zaac.202200278

  日期：2022.11.25

  rate-determining step could be assigned to forming a mononuclear superoxido copper complex. For one of the reactions investigated, a product could be structurally characterized and turned out to be a copper(II) complex with an additional hydroxide as a ligand (most likely caused by a C−H abstraction from the solvent acetone). One of the complexes oxidized thioanisole to the corresponding sulfoxide (conversion of 34 %

  研究了分子氧与含有樟脑衍生配体的铜 (I) 络合物的反应。停流测量显示在低温下形成了双（ μ-氧化）铜络合物。然而，这些中间体不够稳定，无法快速分离和分解。空间上要求更高的烷基减慢了双（μ-oxido) 铜络合物。进行了动力学分析并显示 - 与之前的报告一致 - 可以将速率决定步骤分配给形成单核超氧化铜络合物。对于所研究的其中一个反应，可以对一种产物进行结构表征，结果证明它是一种铜 (II) 络合物，带有一个额外的氢氧化物作为配体（很可能是由溶剂丙酮中的 C−H 萃取引起的）。其中一种复合物将苯甲硫醚氧化成相应的亚砜（根据 GC-MS，转化率为 34%），没有副产物。手性 GC 给出了 14% 的对映体过量。
• Enantioselective ethylation of aldehydes with 1,3-N-donor ligands derived from (+)-camphoric acid
  作者：Dina Murtinho、M. Elisa Silva Serra、A.M.d’A. Rocha Gonsalves

  DOI：10.1016/j.tetasy.2009.12.012

  日期：2010.1

  Derivatives of (+)-camphoric acid were prepared by a short and simple synthetic sequence and proved to be excellent ligands for the enantioselective ethylation of benzaldellyde with diethylzinc, with ees of up to 96% being obtained The most efficient ligand was tested with several aromatic alclehydes and ees of up to 99% were observed Structural features of the ligands are determinant for achieving high enantioselectivities. (c) 2009 Elsevier Ltd All rights reserved
• Novel tridentate ligands derived from (+)-camphoric acid for enantioselective ethylation of aromatic aldehydes
  作者：Dina Murtinho、Camila H. Ogihara、M. Elisa Silva Serra

  DOI：10.1016/j.tetasy.2015.09.017

  日期：2015.12

  Novel tridentate ligands were prepared from (+)-camphoric acid, using simple synthetic sequences. The synthesized ligands were used in enantioselective ethylations of benzaldehydes, showing enantioselectivities up to 92%, at room temperature. Extending the reaction to other aromatic aldehydes, very good results (almost quantitative yields and ee up to 97%, for m-anisaldehyde) were obtained. Structural features such as no substitution in the salicylaldehyde moiety of the Schiff base and an ethyl group in the nitrogen at the Cl position of the cyclopentane ring seem to be essential for obtaining high enantioselectivities. (C) 2015 Elsevier Ltd. All rights reserved.