N-(2-氯乙酰基)-苯甲酰胺 | 7218-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-氯乙酰基)-苯甲酰胺
• 中文别名: 苯甲酰胺,N-(2-氯乙酰基)-
• 英文名称: N-(chloroacetyl)benzamide
• 英文别名: N-Chloracetyl-benzamid；N-(2-chloroacetyl)benzamide
• CAS: 7218-27-1
• 化学式: C₉H₈ClNO₂
• mdl: MFCD03978449
• 分子量: 197.621
• InChiKey: ZDAYXLBYGPADRK-UHFFFAOYSA-N

物化性质

• 熔点：
  157 °C
• 沸点：
  346.9±34.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  N-(2-氯乙酰基)-苯甲酰胺 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以92%的产率得到N-(2-azidoacetyl)benzamide
  参考文献：
  名称：

  Syntheses of Highly Fluorescent GFP-Chromophore Analogues

  摘要：

  Eight B-containing compounds, i.e., 1a-h, were prepared as mimics of the green fluorescent protein (GFP) fluorophore. The underlying concept was that synthetic GFP chromophore analogues are not fluorescent primarily because of free rotation about an aryl-alkene bond (Figure 1b). This rotation is not possible in the beta-barrel of GFP; hence, the molecule is strongly fluorescent. In compounds 1a-h, radiationless decay via this mechanism is prevented by complexation of the BF2 entity. The target materials were prepared via two methods; most were obtained according to the novel route shown in Scheme 1 b, but compound 1f was made via the procedure described in Scheme 2. Both syntheses involved formation of undesired compounds E-4a-h that formed simultaneously with the desired isomeric intermediates Z-4a-h. Both compounds form BF2 adducts, i.e., 1 a-h and 5a-h, respectively. Methods used for spectroscopic characterization and differentiation of compounds in the series 1 and 5 are discussed, and these are supported by single-crystal X-ray diffraction analyses for compounds 1c, 5c, 1f, and 5f. Electronic spectra of compounds la-h and 5a-h were studied in detail. Those in the 5 series were shown to be only weakly fluorescent, but the 1 series were strongly fluorescent compounds (comparable to the boraindacene, BODIPY, dyes). Compounds 1g and 1h are water soluble, and 1h has particularly significant potential as a probe, since it also has a carboxylic acid group for attachment to biomolecules.

  DOI：

  10.1021/ja710388h
• 作为产物：
  描述：

  N-苄基-2-氯乙酰胺 在 N-羟基邻苯二甲酰亚胺 、 氧气 、 2,4,6-三甲基吡啶高氯酸盐 作用下， 以 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以47%的产率得到N-(2-氯乙酰基)-苯甲酰胺
  参考文献：
  名称：

  NHPI-Mediated Electrochemical α-Oxygenation of Amides to Benzimides

  摘要：

  DOI：

  10.1021/acs.joc.2c02700

文献信息

• A Convenient Method for Preparation of α-Imino Carboxylic Acid Derivatives and Application to the Asymmetric Synthesis of Unnatural α-Amino Acid Derivative
  作者：Tsubasa Inokuma、Takahisa Jichu、Kodai Nishida、Akira Shigenaga、Akira Otaka

  DOI：10.1248/cpb.c17-00158

  日期：——

  glycine derivatives for the synthesis of α-imino carboxylic acid derivatives. Using this methodology, utilization of unstable glyoxic acid derivatives was avoided. Furthermore, using this methodology we synthesized novel α-imino carboxylic acid derivatives such as α-imino phenyl ester, perfluoroalkyl etsers, imides, and thioester. The asymmetric Mannich reaction of those novel imine derivatives with 1

  我们在本文中描述了锰（IV）介导的Np-甲氧基苯基（PMP）保护的甘氨酸衍生物的氧化，用于合成α-亚氨基羧酸衍生物。使用这种方法，避免了不稳定的乙二酸衍生物的利用。此外，使用这种方法，我们合成了新型的α-亚氨基羧酸衍生物，例如α-亚氨基苯基酯，全氟烷基酯，酰亚胺和硫代酯。还描述了这些新型亚胺衍生物与1,3-二羰基化合物的不对称曼尼希反应，与使用常规α-亚氨基酯型底物相比，新型α-亚氨基酰亚胺具有更高的化学收率和立体选择性。 。
• A “Traceless” Directing Group Enables Catalytic S_<i>N</i>2 Glycosylation toward 1,2-<i>cis</i>-Glycopyranosides
  作者：Xu Ma、Zhitong Zheng、Yue Fu、Xijun Zhu、Peng Liu、Liming Zhang

  DOI：10.1021/jacs.1c04584

  日期：2021.8.11

  Generally applicable and stereoselective formation of 1,2-cis-glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2-trans glycosyl ester donors. This SN2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a

  1,2-顺式-吡喃糖苷键的普遍适用和立体选择性形成仍然是碳水化合物化学中长期追求但尚未实现的目标。这项工作通过在 1,2-反式糖基酯供体的异头位置上的立体倒置推进了应对这一挑战的策略。这种 S N 2 糖基化是在金催化下通过以恶唑为基础的导向基团实现的，该导向基团最佳地束缚在离去基团上，并在温和的催化条件下以大多数优异的产率和良好的选择性实现。该策略也适用于寡糖的合成。
• Substituted mercapto acid amides and their use
  申请人：Merck & Co., Inc.

  公开号：US04216160A1

  公开（公告）日：1980-08-05

  Substituted mercapto acid amides are prepared, and are useful as immunoregulants for correcting an imbalance of immune homeostasis, particularly as immunostimulants in the treatment of autoimmune and immune deficient diseases and disorders.

  取代巯基酸酰胺被制备出来，并且作为免疫调节剂在纠正免疫稳态失衡方面非常有用，特别是作为免疫刺激剂用于治疗自身免疫和免疫缺陷疾病和疾病。
• Inhibitory effects of N-(acryloyl)benzamide derivatives on tyrosinase and melanogenesis
  作者：Sanggwon Lee、Sultan Ullah、Chaeun Park、Hee Won Lee、Dongwan Kang、Jungho Yang、Jinia Akter、Yujin Park、Pusoon Chun、Hyung Ryong Moon

  DOI：10.1016/j.bmc.2019.07.034

  日期：2019.9

  and synthesized ten NAB (N-(acryloyl)benzamide) derivatives (1a-1j) using the Horner-Wadsworth-Emmons olefination of diethyl (2-benzamido-2-oxoethyl)phosphonate and appropriate benzaldehydes. A mushroom tyrosinase inhibitory assay showed compounds 1a (36.71 ± 2.14% inhibition) and 1j (25.99 ± 2.77% inhibition) inhibited tyrosinase more than the other eight NAB derivatives and kojic acid (21.56 ± 2

  酪氨酸酶的靶向已被证明是识别美白皮肤安全，有效和有效的酪氨酸酶抑制剂的最佳方法。我们使用（2-benzamido-2-oxoethyl）膦酸二乙酯和合适的苯甲醛的Horner-Wadsworth-Emmons烯化反应设计并合成了十种NAB（N-（丙烯酰基）苯甲酰胺）衍生物（1a-1j）。蘑菇酪氨酸酶抑制试验显示化合物1a（抑制36.71±2.14％）和1j（抑制25.99±2.77％）抑制酪氨酸酶的作用比其他八种NAB衍生物和曲酸（抑制21.56±2.93％）更大，对接研究表明1a（ -6.9 kcal / mol）和1j（-7.5 kcal / mol）对酪氨酸酶的结合亲和力比曲酸（-5.7 kcal / mol）强。在25μM的浓度下，1a和1j对B16F10黑色素瘤细胞无毒，并表现出更强的酪氨酸酶抑制作用（59。比曲酸（抑制50.30％）或熊果苷（400μM抑制41.78％）分别高70％和76
• PDE10 MODULATORS
  申请人：Bachmann Stephan

  公开号：US20130059833A1

  公开（公告）日：2013-03-07

  The present invention relates to compounds of formula (I) wherein R 1 , R 2 , R 3 , R 5 , W, X, X 1 , Y, Y 1 , Z and Z 1 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit PDE10A and can be used in the treatment of CNS disorders such as schizophrenia, Alzheimer's disease, and Parkinson's disease.

  本发明涉及式(I)的化合物，其中R1、R2、R3、R5、W、X、X1、Y、Y1、Z和Z1如描述和权利要求中定义，并且其生理上可接受的盐。这些化合物抑制PDE10A，可用于治疗中枢神经系统疾病，如精神分裂症、阿尔茨海默病和帕金森病。