N,N-dimethyl-2,2,2-triphenylacetamide | 66415-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N,N-dimethyl-2,2,2-triphenylacetamide
• 英文别名: NN-dimethyl-2,2,2-triphenylacetamide；Triphenylessigsaeure-dimethylamid；N,N-Dimethyl-triphenyl-acetamid
• CAS: 66415-28-9
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: JGBIXOAQARJTNI-UHFFFAOYSA-N

物化性质

• 熔点：
  217.5 °C
• 沸点：
  471.6±44.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2,2,2-triphenylacetamide 在 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 14.0h， 以61%的产率得到N,N-dimethyl-o-benzhydrylbenzamid
  参考文献：
  名称：

  通过氢化钠/碘化物复合物进行酰胺导向的CH磺化反应。

  摘要：

  在碘化钠（NaI）或碘化锂（LiI）的存在下，氢化钠（NaH）可以实现酰胺定向的邻位和横向CH磺化的新方案。瞬态有机钠中间体可以转化为官能化的芳族化合物。

  DOI：

  10.1002/anie.201702512
• 作为产物：
  描述：

  三苯基乙酸 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N,N-dimethyl-2,2,2-triphenylacetamide
  参考文献：
  名称：

  通过氢化钠/碘化物复合物进行酰胺导向的CH磺化反应。

  摘要：

  在碘化钠（NaI）或碘化锂（LiI）的存在下，氢化钠（NaH）可以实现酰胺定向的邻位和横向CH磺化的新方案。瞬态有机钠中间体可以转化为官能化的芳族化合物。

  DOI：

  10.1002/anie.201702512

文献信息

• Palladium-Catalyzed Conversion of Benzylic and Allylic Halides into α-Aryl and β,γ-Unsaturated Tertiary Amides by the Use of a Carbamoylsilane
  作者：Robert F. Cunico、Rajesh K. Pandey

  DOI：10.1021/jo0512406

  日期：2005.10.1

  Treatment of allylic and benzylic halides with N,N-dimethylcarbamoyl(trimethyl)silane in the presence of tetrakis(triphenylphosphine)palladium(0) affords tertiary amides, which arise from the replacement of the halogen by the N,N-dimethylcarbamoyl group.

  在四（三苯基膦）钯（0）​​存在下，用N，N-二甲基氨基甲酰基（三甲基）硅烷处理烯丙基和苄基卤化物可得到叔酰胺，这是由N，N-二甲基氨基甲酰基取代卤素而产生的。
• Novel Inhibitors of the Gardos Channel for the Treatment of Sickle Cell Disease
  作者：Grant A. McNaughton-Smith、J. Ford Burns、Jonathan W. Stocker、Gregory C. Rigdon、Christopher Creech、Susan Arrington、Tara Shelton、Lucia de Franceschi

  DOI：10.1021/jm070663s

  日期：2008.2.1

  Sickle cell disease (SCD) is a hereditary condition characterized by deformation of red blood cells (RBCs). This phenomenon is due to the presence of abnormal hemoglobin that polymerizes upon deoxygenation. This effect is exacerbated when dehydrated RBCs experience a loss of both water and potassium salts. One critical pathway for the regulation of potassium efflux from RBCs is the Gardos channel, a calcium-activated potassium channel. This paper describes the synthesis and biological evaluation of a series of potent inhibitors of the Gardos channel. The goal was to identify compounds that were potent and selective inhibitors of the channel but had improved pharmacokinetic properties compared to 1, Clotrimazole. Several triarylamides such as 10 and 21 were potent inhibitors of the Gardos channel (IC50 of < 10 nM) and active in a mouse model of SCD. Compound 21 (ICA-17043) was advanced into phase 3 clinical trials for SCD.
• CH-Acidit�t in ?-Stellung zum N-Atom inN,N-dialkylamiden mitsterisch gesch�tzter Carbonylgruppe zur nucleophilen minoalkylierung
  作者：Rainer Schlecker、Dieter Seebach、Winfried Lubosch

  DOI：10.1002/hlca.19780610144

  日期：1978.1.25

  CH‐Acidity in α‐position to the N‐Atom of N, N‐Dialkylamides with Sterically Protected Carbonyl Groups Contribution to the Nucleophilic Amino AlkylationSterically protected amides 1 such as the 2,4,6‐triisopropyl‐benzoic acid derivatives 3, 8b and 10 undergo readily H/Li‐exchange with s‐butyllithium at the CH3N‐ or CH2N‐groups. The resulting organolithium compounds (cf. 9, 11) are alkylated and hydroxyalkylated with primary haloalkanes, aldehydes, and ketones under chain elongation in the amine position of the amides. The (E/Z)‐rotamers of the dialkylamides 7 and 8are separated by chromatography; the amides 4–6, 12, and 13 formally derived from β‐hydroxyamines are obtained in the (Z)‐form only. The configurational (E/Z)‐assignments follow from NMR. and IR. data. The erythro and threo configuration of the two diastereomeric amides 12a and 12b are tentatively concluded from Eu(fod)3‐1H‐NMR.‐shift experiments. The results strongly suggest that the H/Li‐exchange takes place regioselectively at the CHN group which is in cis‐position to the CO double bond (→14). The methyl 2,4,6‐tri(t‐butyl)benzoate (18) can also be deprotonated to the lithium acyloxymethanide 19 which is trapped by alkylation with 1‐iodooctane (→20). – The steric protection of the carbonyl groups in the products 4–8, 10, 12, 13, and 20 prevents their ready hydrolysis to amines and alcohols, respectively. Therefore, triphenylacetic acid derivatives 21 rather than 2,4,6‐triisopropylbenzoic acid derivatives for use in the electrophilic substitution of equation (1) are recommended. The trityl group in 21 may be considered a C‐leaving‐group (CC protective group, cf. 22, 23). The acetamide 25 reacts readily (→26) and then with electrophiles to give products 27a–c. As shown in the Table, the amides 27 are cleaved under a variety of conditions with formation of triphenylmethane. LiAlH4 produces a tertiary amine, CH3Li a secondary amine, and dissolving alkali metals/naphthalene under aprotic conditions mixtures of secondary amine and its formamide (hydrolysed by acid treatment). Thus the overall process (2) is feasible.
• WYKYPIEL, W.;LOHMANN, J. -J.;SEEBACH, D., HELV. CHIM. ACTA, 1981, 64, N 5, 1337-1346
  作者：WYKYPIEL, W.、LOHMANN, J. -J.、SEEBACH, D.

  DOI：——

  日期：——
• Amide-Directed C−H Sodiation by a Sodium Hydride/Iodide Composite
  作者：Yinhua Huang、Guo Hao Chan、Shunsuke Chiba

  DOI：10.1002/anie.201702512

  日期：2017.6.1

  A new protocol for amide-directed ortho and lateral C-H sodiation is enabled by sodium hydride (NaH) in the presence of either sodium iodide (NaI) or lithium iodide (LiI). The transient organosodium intermediates could be transformed into functionalized aromatic compounds.

  在碘化钠（NaI）或碘化锂（LiI）的存在下，氢化钠（NaH）可以实现酰胺定向的邻位和横向CH磺化的新方案。瞬态有机钠中间体可以转化为官能化的芳族化合物。