N-[2-hydroxy-1-(1-hydroxymethyl)ethyl]phenylacetamide | 223560-31-4

• 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: N-[2-hydroxy-1-(1-hydroxymethyl)ethyl]phenylacetamide
• 英文别名: N,N-bis(2-hydroxyethyl)-2-phenylacetamide；phenyl-acetic acid-(β,β'-dihydroxy-isopropylamide)；Phenyl-essigsaeure-(β,β'-dihydroxy-isopropylamid)；N-(1,3-dihydroxypropan-2-yl)-2-phenylacetamide
• CAS: 223560-31-4
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: CJNFLGGQMAXLMS-UHFFFAOYSA-N

物化性质

• 熔点：
  129-132 °C
• 沸点：
  505.9±50.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-hydroxy-1-(1-hydroxymethyl)ethyl]phenylacetamide 在 四溴环己二烯-1-酮 、 草酸 、 silica gel 、 原甲酸三乙酯 、 三氟乙酸 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 40.0h， 生成 (cis)-[N-2-(1,3-dioxolan-2-yl)methyl-1,3-dioxan-5-yl]phenylacetamide
  参考文献：
  名称：

  Novel synthesis and anti-inflammatory activities of 2,5-disubstituted-dioxacycloalkanes

  摘要：

  A novel stereospecific synthetic route to obtain a series of 2,5-disubstituted-dioxacycloalkanes is reported. Using an in vivo inhibition assay by monitoring xylene-induced ear edema in mice, the structure-activity relationship of the dioxacycloalkane compounds was studied, and compounds possessing high anti-inflammatory activity were identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.032
• 作为产物：
  描述：

  N-(benzoyl)-L-serine methyl ester 在 钾硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以91%的产率得到N-[2-hydroxy-1-(1-hydroxymethyl)ethyl]phenylacetamide
  参考文献：
  名称：

  致力于化学预防剂的发展。第1部分：新型2，5-二取代的二氧杂环烷烃的设计，合成和抗炎活性。

  摘要：

  设计并通过立体选择性合成方法合成了一类新的2,5-二取代-二氧杂环戊烷作为癌症的化学预防剂。使用二甲苯诱导的小鼠耳朵水肿模型测试了这些化合物的抗炎活性。这些化合物中的某些具有比阿司匹林更好的抗炎活性，这表明它们可以进一步发展为潜在的抗炎药先导化合物。另外，这些抗炎药的治疗并未延长小鼠的尾巴出血时间。还分析了这些化合物之间的结构/活性关系。

  DOI：

  10.1016/j.bmc.2007.05.013

文献信息

• Amidation of Esters with Amino Alcohols Using Organobase Catalysis
  作者：Nicola Caldwell、Peter S. Campbell、Craig Jamieson、Frances Potjewyd、Iain Simpson、Allan J. B. Watson

  DOI：10.1021/jo501929c

  日期：2014.10.3

  the base-mediated amidation of unactivated esters with amino alcohol derivatives is reported. Investigations into mechanistic aspects of the process indicate that the reaction involves an initial transesterification, followed by an intramolecular rearrangement. The reaction is highly general in nature and can be extended to include the synthesis of oxazolidinone systems through use of dimethyl carbonate

  报道了一种催化方案，用于未活化的酯与氨基醇衍生物的碱介导的酰胺化。对过程的机械方面的研究表明，该反应涉及初始的酯交换反应，然后是分子内的重排。该反应本质上是高度通用的，并且可以扩展至包括通过使用碳酸二甲酯合成恶唑烷酮系统。
• Behrens et al., Journal of Biological Chemistry, 1948, vol. 175, p. 771,778
  作者：Behrens et al.

  DOI：——

  日期：——
• Toward the development of chemoprevention agents. Part II: Chemo-enzymatic synthesis and anti-inflammatory activities of a new class of 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes
  作者：Keli Gu、Lanrong Bi、Ming Zhao、Chao Wang、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2007.06.018

  日期：2007.9

  A new series of optically pure 5-amino-2-substitutedphenyl-1,3-dioxacyclozilkanes were designed and synthesized via a chemo-enzymatic combined method to develop new chemoprevention agents. Twenty-four of newly synthesized compounds significantly inhibited xylene-induced rat ear edema and exhibited comparable or better anti-inflammatory activities than the reference drug aspirin. Treatment of these anti-inflammatory agents did not prolong the tail bleeding time in rat. In addition, 5-amino-2-substitutedphenyl- I 3-dioxacycloalkanes exhibited good membrane permeability based on in vitro Caco-2 cell monolayer permeability assay. Furthermore, some preliminary structure-activity relationships were further analyzed among these compounds. Taken together, 5-amino-2-substitutedphenyl-1,3-dioxacycloalkanes may represent a new class of anti-inflammatory drugs with safer pharmacological profile. (c) 2007 Elsevier Ltd. All rights reserved.
• Nu-dihydroxypropyl phenylacetamide
  申请人：LILLY CO ELI

  公开号：US02449194A1

  公开（公告）日：1948-09-14
• Toward the development of chemoprevention agents. Part 1: Design, synthesis, and anti-inflammatory activities of a new class of 2,5-disubstituted-dioxacycloalkanes
  作者：Keli Gu、Lanrong Bi、Ming Zhao、Chao Wang、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2007.05.013

  日期：2007.7

  A new class of 2,5-disubstituted-dioxacycloalkanes were designed and synthesized via stereoselective synthetic method as cancer chemoprevention agents. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model. Some of these compounds exhibited comparable or better anti-inflammatory activities than that of aspirin suggesting that they can be further

  设计并通过立体选择性合成方法合成了一类新的2,5-二取代-二氧杂环戊烷作为癌症的化学预防剂。使用二甲苯诱导的小鼠耳朵水肿模型测试了这些化合物的抗炎活性。这些化合物中的某些具有比阿司匹林更好的抗炎活性，这表明它们可以进一步发展为潜在的抗炎药先导化合物。另外，这些抗炎药的治疗并未延长小鼠的尾巴出血时间。还分析了这些化合物之间的结构/活性关系。