methyl 2-(diethylamino)-2-phenylacetate | 105394-78-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(diethylamino)-2-phenylacetate
• CAS: 105394-78-3
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: YPHCUUUXRYMPHX-UHFFFAOYSA-N

物化性质

• 沸点：
  123-129 °C(Press: 3 Torr)
• 密度：
  1.0135 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-pyridyllithium 、 methyl 2-(diethylamino)-2-phenylacetate 以 四氢呋喃 为溶剂， 生成 (+/-)-2-(diethylamino)-2-phenyl-1,1-dipyridin-3-ylethanol
  参考文献：
  名称：

  Discovery of triarylethanolamine inhibitors of the Kv1.5 potassium channel

  摘要：

  A series of triarylethanolamine inhibitors of the Kv1.5 potassium channel have been prepared and evaluated for their effects in vitro and in vivo. The structure-activity relationship (SAR) studies described herein led to the development of potent, selective and orally active inhibitors of Kv1.5. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.005
• 作为产物：
  描述：

  苯甲酰甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 、 盐酸羟胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 methyl 2-(diethylamino)-2-phenylacetate
  参考文献：
  名称：

  Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents

  摘要：

  Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.091

文献信息

• N–H insertion reactions of rhodium carbenoids. Part 1. Preparation of α-amino acid and α-aminophosphonic acid derivatives
  作者：Enrique Aller、Richard T. Buck、Martin J. Drysdale、Leigh Ferris、David Haigh、Christopher J. Moody、Neil D. Pearson、J. Bobby Sanghera

  DOI：10.1039/p19960002879

  日期：——

  Rhodium(II) acetate-catalysed decomposition of diazophenylacetates 1 and 3 in the presence of a range of N–H compounds results in an N–H insertion reaction of the intermediate carbenoids and formation of N-substituted phenylglycine derivatives 2 and 4. The corresponding reactions of dimethyl α-diazobenzylphosphonate 5 constitute a simple route to aminophosphonates 6.

  在一定范围的N–H化合物存在下，乙酸铑（II）催化的重氮苯基乙酸酯1和3的分解导致中间类胡萝卜素的N–H插入反应并形成N-取代的苯基甘氨酸衍生物2和4。 α-二重氮苄基膦酸二甲酯5的反应构成了氨基膦酸酯6的简单路线。
• Electrolysis promoted reductive amination of electron-deficient aldehydes/ketones: a green route to the racemic clopidogrel
  作者：Qianyun Zhang、Wen Zhu、Jinzhong Yao、Xiaofang Li、Hongwei Zhou

  DOI：10.1039/c8ob02500b

  日期：——

  An electrocatalytic reductive amination of electron-deficient aldehydes/ketones was developed, which could be used in the synthesis of functionalized tertiary amines and large scale preparation of racemic clopidogrel. A plausible mechanism involving an iminium cation intermediate was proposed.

  开发了一种电子缺陷型醛/酮的电催化还原胺化反应，可用于功能化叔胺的合成和外消旋氯吡格雷的大规模制备。提出了一种涉及亚胺阳离子中间体的合理机制。
• Diastereoselective Petasis Mannich reactions accelerated by hexafluoroisopropanol: a pyrrolidine-derived arylglycine synthesis
  作者：Kausik K. Nanda、B. Wesley Trotter

  DOI：10.1016/j.tetlet.2005.01.151

  日期：2005.3

  A diastereoselective synthesis of pyrrolidine-derived arylglycines has been developed using the Petasis boronic acid Mannich reaction. High diastereoselectivities in the reactions of chiral amines, aryl boronic acids, and glyoxylic acid monohydrate have been demonstrated for the first time. Key to the implementation of this method is the discovery that hexafluoroisopropanol accelerates the Petasis process

  使用Petasis硼酸曼尼希反应已经开发了非对映选择性合成吡咯烷衍生的芳基甘氨酸的方法。首次证明在手性胺，芳基硼酸和乙醛酸一水合物的反应中具有很高的非对映选择性。实施该方法的关键是发现六氟异丙醇可加快Petasis过程，将反应时间从数天缩短至不到24小时。
• Hegedus, Louis S.; Schwindt, Mark A.; De Lombaert, Stéphane, Journal of the American Chemical Society, 1990, vol. 112, # 6, p. 2264 - 2273
  作者：Hegedus, Louis S.、Schwindt, Mark A.、De Lombaert, Stéphane、Imwinkelried, Rene

  DOI：——

  日期：——
• Copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals under atmosphere leading to α-aryl glycine derivatives and diarylmethylamine derivatives
  作者：Norio Sakai、Hiroaki Hori、Yoshihiro Yoshida、Takeo Konakahara、Yohei Ogiwara

  DOI：10.1016/j.tet.2015.05.068

  日期：2015.7

  We demonstrated a copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals leading to the synthesis of alpha-aryl glycines and diarylmethylamines. Under an ambient atmosphere, this catalytic system could be applied to the activation of a C(sp(3))-O bond of N,O-acetals with an ester and an aryl group, or without a coordinating substituent, as well as to a C(sp(3))-N bond of N,N-aminals. (C) 2015 Elsevier Ltd. All rights reserved.