benzyl N-[(3-bromophenyl)methylidene]carbamate | 1322693-67-3

• 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: benzyl N-[(3-bromophenyl)methylidene]carbamate
• CAS: 1322693-67-3
• 化学式: C₁₅H₁₂BrNO₂
• 分子量: 318.17
• InChiKey: YLCBFTJNNAQLFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl N-[(3-bromophenyl)methylidene]carbamate 在 C₁₇H₂₁F₆N₃O 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 89.0h， 生成
  参考文献：
  名称：

  One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis

  摘要：

  The highly enantioselective preparation of trisubstituted pyrrolidinc derivatives employing a one-pot nitro-Mannich/hydroamination cascade is reported. This cascade approach utilizes an asymmetric bifunctional organo-catalytic nitro-Mannich reaction followed by a gold-catalyzed allene hydroamination reaction. The products are afforded in good yields and excellent diastereo- and enantioselectivities.

  DOI：

  10.1021/cs401008v

文献信息

• Stereoselective Organocatalyzed Synthesis of α-Fluorinated β-Amino Thioesters and Their Application in Peptide Synthesis
  作者：Elena Cosimi、Oliver D. Engl、Jakub Saadi、Marc-Olivier Ebert、Helma Wennemers

  DOI：10.1002/anie.201607146

  日期：2016.10.10

  β‐amino thioesters were obtained in high yields and stereoselectivities by organocatalyzed addition reactions of α‐fluorinated monothiomalonates (F‐MTMs) to N‐Cbz‐ and N‐Boc‐protected imines. The transformation requires catalyst loadings of only 1 mol % and proceeds under mild reaction conditions. The obtained addition products were readily used for coupling‐reagent‐free peptide synthesis in solution

  α-β氟化氨基硫酯以高产率和立体选择性由α氟化monothiomalonates（F-MTMS）至organocatalyzed加成反应得到Ñ -Cbz-和Ñ -Boc保护的亚胺。该转化仅需要催化剂负载量为1mol％，并且在温和的反应条件下进行。所获得的加成产物易于在溶液中和固相上用于无偶联剂的肽合成。由晶体结构和NMR光谱分析确定，α-氟-β-（碳）酰胺基部分显示出独特的构象偏好。
• Stereoselective Metal-Free Synthesis of β-Amino Thioesters with Tertiary and Quaternary Stereogenic Centers
  作者：Annette Bahlinger、Sven P. Fritz、Helma Wennemers

  DOI：10.1002/anie.201310532

  日期：2014.8.11

  β‐Amino thioesters are important natural building blocks for the synthesis of numerous bioactive molecules. An organocatalyzed Mannich reaction was developed which provides direct and highly stereoselective access to acyclic β2‐ and β2,3,3‐amino thioesters with adjacent tertiary and quaternary stereocenters. Mechanistic studies showed that the stereochemical course of the reaction can be controlled

  β-氨基硫酯是许多生物活性分子合成的重要天然组成部分。一个organocatalyzed曼尼希反应被开发，其提供到无环β直接和高立体选择性访问2 -和β 2,3,3 -氨基硫酯与相邻的三级和四级立体。机理研究表明，可以通过选择底物来控制反应的立体化学过程。的β氨基硫酯被进一步官能化，例如，立体选择性脱羧访问β 2,3 -frameworks。另外，β-氨基硫酯的值在无偶联试剂的肽合成中得到显示。
• Direct asymmetric Mannich reaction of phthalides: facile access to chiral substituted isoquinolines and isoquinolinones
  作者：Jie Luo、Haifei Wang、Fangrui Zhong、Jacek Kwiatkowski、Li-Wen Xu、Yixin Lu

  DOI：10.1039/c2cc31439h

  日期：——

  The first Mannich reaction employing phthalides using a quinidine-based multifunctional catalyst has been developed. The reported method led to the synthesis of 3,3-disubstituted phthalide derivatives in excellent yields, with good diastereo- and enantioselectivities. Convenient synthesis of chiral isoquinolinones and isoquinolines has also been demonstrated.

  首次利用基于奎尼丁的多功能催化剂进行邻苯二甲酸内酯的Mannich反应已被开发。所报道的方法合成了3,3-二取代的邻苯二甲酸内酯衍生物，产率极高，且具有良好的非对映选择性和对映选择性。此外，便捷合成手性异喹啉酮和异喹啉的示例也已得到证明。
• Chiral Dinuclear Benzyliminobinaphthoxy‐Palladium Catalyst for Asymmetric Mannich Reaction of Aldimines and Isatin‐Derived Ketimines with Alkylmalononitriles
  作者：Ayu Nakamura、Satoru Kuwano、Junchuan Sun、Kensuke Araseki、Eri Ogino、Takayoshi Arai

  DOI：10.1002/adsc.202000447

  日期：2020.8.4

  A newly developed dinuclear bis(benzylimino)binaphthol (BIB )−Pd complex showed good catalytic activity for the Mannich reaction of aldimines and isatin‐derived ketimines with alkylmalononitriles to give the products in a highly enantioselective manner.

  一种新开发的双核双（苄基亚氨基）联萘酚（BIB）-Pd络合物对醛亚胺和源自靛红的酮亚胺与烷基丙二腈的曼尼希反应具有良好的催化活性，从而以高度对映选择性的方式提供了产物。
• Enantioselective Friedel-Crafts Aminoalkylation Catalyzed by Chiral Ammonium 1,1′-Binaphthyl-2,2′-disulfonates
  作者：Kazuaki Ishihara、Manabu Hatano、Yoshihiro Sugiura、Matsujiro Akakura

  DOI：10.1055/s-0030-1260538

  日期：2011.6

  A catalytic enantioselective Friedel-Crafts aminoalkylation between aromatic aldimines and N-benzylpyrrole with the use of a homogeneous chiral ammonium salt, (R)-BINSA-N,N-dimethylbutylamine, as a dynamic Brønsted acid-Brønsted base catalyst, is reported. Unlike the results with conventional catalysts, remarkably high reactivity was established at -78 ˚C within 30 minutes, and the corresponding aryl(1H-pyrrol-2-yl)methanamines were obtained with good to high enantioselectivities.

  报道了使用均相手性铵盐 (R)-BINSA-N,N-二甲基丁胺作为动态布朗斯台德酸-布朗斯台德碱催化剂，在芳香醛亚胺和 N-苄基吡咯之间进行催化对映选择性弗里德尔-克来福特氨烷基化反应。与传统催化剂的结果不同，在-78℃下30分钟内建立了非常高的反应活性，并获得了具有良好至高对映选择性的相应芳基(1H-吡咯-2-基)甲胺。