(S)-2-amino-N-benzhydryl-N,3,3-trimethylbutanamide | 1186602-26-5

• 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-amino-N-benzhydryl-N,3,3-trimethylbutanamide
• 英文别名: (2S)-2-amino-N-benzhydryl-N,3,3-trimethylbutanamide
• CAS: 1186602-26-5
• 化学式: C₂₀H₂₆N₂O
• 分子量: 310.439
• InChiKey: SWIKXUGQTHKUNB-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-benzhydryl-N,3,3-trimethylbutanamide 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (S)-N-benzhydryl-2-(3-cyclohexylthioureido)-N,3,3-trimethylbutanamide
  参考文献：
  名称：

  Enantioselective Formal Aza-Diels–Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas

  摘要：

  A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.

  DOI：

  10.1021/ja310718f
• 作为产物：
  描述：

  N-Boc-L-叔亮氨酸 在 盐酸 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 (S)-2-amino-N-benzhydryl-N,3,3-trimethylbutanamide
  参考文献：
  名称：

  硫脲阴离子结合催化不对称有机催化合成 α-氨基次膦酸盐

  摘要：

  通过硫脲催化剂的阴离子结合催化，以高对映选择性获得了对立构α-氨基次膦酸盐，进一步扩大了可用于此类催化的亲核试剂的范围。

  DOI：

  10.1002/ejoc.202301212

文献信息

• COMPOUNDS AND RELATED METHODS OF USE
  申请人：Jacobsen Eric N.

  公开号：US20130066109A1

  公开（公告）日：2013-03-14

  Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.

  本文描述了式（I）的化合物、相关组合物及其用途，例如在形成α-氨基酸或其前体（如α-氨基腈）中的应用。
• Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions
  作者：Dennis A. Kutateladze、Eric N. Jacobsen

  DOI：10.1021/jacs.1c10890

  日期：2021.12.8

  hydrogen chloride (HCl) and chiral dual-hydrogen-bond donors (HBDs) is applied successfully to highly enantioselective Prins cyclization reactions of a wide variety of simple alkenyl aldehydes. The optimal chiral catalysts were designed to withstand the strongly acidic reaction conditions and were found to induce rate accelerations of 2 orders of magnitude over reactions catalyzed by HCl alone. We propose

  氯化氢 (HCl) 和手性双氢键供体 (HBD) 的协同不对称催化已成功应用于各种简单烯基醛的高度对映选择性 Prins 环化反应。最佳的手性催化剂被设计为能够承受强酸性反应条件，并且发现与单独使用 HCl 催化的反应相比，其速率加速了 2 个数量级。我们提出，强无机酸和手性氢键供体催化剂的组合可能代表了在需要高酸性条件的反应中诱导对映选择性的一般策略。
• Compound reagents and method for synthesizing enantiomerically enriched amino acids
  申请人：Jacobsen Eric N.

  公开号：US08859812B2

  公开（公告）日：2014-10-14

  Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.

  本文描述了式(I)的化合物、相关组合物及其用途，例如在α-氨基酸或其前体（如α-氨基腈）的形成中的使用。
• Mechanism of Amido-Thiourea Catalyzed Enantioselective Imine Hydrocyanation: Transition State Stabilization via Multiple Non-Covalent Interactions
  作者：Stephan J. Zuend、Eric N. Jacobsen

  DOI：10.1021/ja9058958

  日期：2009.10.28

  An experimental and computational investigation of amido-thiourea promoted imine hydrocyanation has revealed a new and unexpected mechanism of catalysis. Rather than direct activation of the imine by the thiourea, as had been proposed previously in related systems, the data are consistent with a mechanism involving catalyst-promoted proton transfer from hydrogen isocyanide to imine to generate diastereomeric iminium/cyanide ion pairs that are bound to catalyst through multiple noncovalent interactions; these ion pairs collapse to form the enantiomeric alpha-aminonitrile products. This mechanistic proposal is supported by the observation of a statistically significant correlation between experimental and calculated enantioselectivities induced by eight different catalysts (P << 0.01). The computed models reveal a basis for enantioselectivity that involves multiple stabilizing and destabilizing interactions between substrate and catalyst, including thiourea-cyanide and amide-iminium interactions.
• US8859812B2
  申请人：——

  公开号：US8859812B2

  公开（公告）日：2014-10-14