benzylammonium formate

• 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: benzylammonium formate
• 英文别名: HCOONH3Bn；benzylamine; formate；Benzylamin; Formiat；Formic acid;phenylmethanamine
• 化学式: CH₂O₂*C₇H₉N
• 分子量: 153.181
• InChiKey: IPTSRSQBXHITET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.21
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzylammonium formate 在 吡啶 、 titanium(IV) isopropylate 、 甲醇 、 METHYLTITANIUM TRIISOPROPOXIDE 、 氨 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 28.0h， 生成 (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-N-benzyl-5-(hydroxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol
  参考文献：
  名称：

  Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions

  摘要：

  The titanium-mediated cyclopropanation reaction using Ti((OPr)-Pr-i)(3)Me/EtMgBr/BF3 center dot OEt2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2S,3S,4R,5S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (38), which has the same absolute configuration as L-fucose, is a moderate (IC50=44 mu M), but selective, inhibitor of alpha-L-fucosidase from human placenta. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.024

文献信息

• One-pot synthesis of pyrrole derivatives from (E)-1,4-diaryl-2-butene-1,4-diones
  作者：H Surya Prakash Rao、S Jothilingam

  DOI：10.1016/s0040-4039(01)01334-x

  日期：2001.9

  2,5-Di- and 1,2,5-trisubstituted pyrrole derivatives can be prepared conveniently from (E)-1,4-diaryl-2-butene-1,4-diones in a one-pot operation through domino-pathways via palladium-assisted transfer hydrogenation followed by a Paal–Knorr reaction using ammonium formate and its analogs.

  可通过一锅操作通过多米诺途径方便地从（E）-1,4-二芳基-2-丁烯-1,4-二酮制备2,5-二-和1,2,5-三取代的吡咯衍生物通过钯辅助的转移氢化反应，然后使用甲酸铵及其类似物进行Paal-Knorr反应。
• Synthesis of 5-substituted-3,4-dihydroxycyanopyrrolidines. An easy access to polyhydroxyprolines
  作者：Marina Moura、Sébastien Delacroix、Denis Postel、Albert Nguyen Van Nhien

  DOI：10.1016/j.tet.2009.01.108

  日期：2009.4

  A novel procedure for the synthesis of cyanopyrrolidines is presented. Starting from conveniently functionalized d-ribose, d-mannose, d-(l)-arabinose, the compounds were efficiently synthesised in four steps in overall good yields. Transformation into proline derivatives and preliminary evaluation of these derivatives in organocatalysis is also described.

  提出了一种合成氰基吡咯烷的新方法。从方便地官能化的d-核糖，d-甘露糖，d-（l）-阿拉伯糖开始，以四个步骤有效地合成了化合物，总体上具有良好的收率。还描述了向脯氨酸衍生物的转化以及这些衍生物在有机催化中的初步评估。
• Synthesis of 2-aminocyclopropyl pyrrolidines from glycoaminonitriles
  作者：Delphine Declerck、Solen Josse、Albert Nguyen Van Nhien、Denis Postel

  DOI：10.1016/j.tetlet.2009.02.135

  日期：2009.5

  We have developed an expedient method for the synthesis of 2-aminocyclopropyl pyrrolidines from carbohydrate-derived α-aminonitriles involving up to five or six steps, the key step being the titanium-mediated aminocyclopropanation on the aminonitrile moiety, followed by cleavage of the protecting groups.

  我们已经开发了一种从碳水化合物衍生的α-氨基腈合成2个氨基环丙基吡咯烷的简便方法，涉及多达五或六个步骤，关键步骤是在氨基腈部分进行钛介导的氨基环丙烷化，然后裂解保护基。
• METHOD FOR ACYLATING HEXAKIS (ARYLMETHYL) HEXAAZAISOWURTZITANE
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP1024141A1

  公开（公告）日：2000-08-02

  A method for acylating a hexakis(arylmethyl)hexaazaisowurtzitane (WB6) by reductive dearylmethylation in the presence of an acylating agent, which comprises contacting (a) a WB6 and (b) a heterogeneous reduction catalyst with each other in the presence of (c) an acylating agent and (d) a reducing agent in (e) a solvent for WB6 (a), thereby performing a reductive dearylmethylation/acylation reaction of WB6 (a), wherein there is no contact between WB6 (a) and heterogeneous reduction catalyst (b) in the absence of any of acylating agent (c) and reducing agent (d). The method of the present invention is commercially advantageous in that the decomposition of a hexaazaisowurtzitane skeleton, Which is likely to occur at the initial stage of the acylation reaction of a WB6 as a starting material, can be very effectively suppressed, so that desired tetraacylhexaazaisowurtzitane derivatives can be stably produced in high yield.

  从而对 WB6 (a) 进行还原性脱芳基甲基化/酰化反应，其中在没有酰化剂 (c) 和还原剂 (d) 的情况下，WB6 (a) 和异相还原催化剂 (b) 之间没有接触。本发明的方法在商业上的优势在于可以非常有效地抑制六氮唑脲烷骨架的分解，这种分解可能发生在作为起始原料的 WB6 的酰化反应的初始阶段，因此可以高产率稳定地生产出所需的四乙酰基六氮唑脲烷衍生物。
• DE482943
  申请人：——

  公开号：——

  公开（公告）日：——