N-cinnamoyl-1-naphthylamine | 55255-53-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-cinnamoyl-1-naphthylamine
• 英文别名: N-(naphthalen-1-yl)cinnamamide；α-Naphthylcinnamamide；N-[1]naphthyl-cinnamamide；N-[1]Naphthyl-cinnamamid；Zimtsaeure-α-naphthylamid；(2E)-N-(naphthalen-1-yl)-3-phenylprop-2-enamide；N-naphthalen-1-yl-3-phenylprop-2-enamide
• CAS: 55255-53-3
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: PRAXZOCGSMFITR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-cinnamoyl-1-naphthylamine 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以55%的产率得到Naphthalen-1-yl-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-amine
  参考文献：
  名称：

  Sharma, Shalabh; Srivastava, Virendra Kishore; Kumar, Ashok, Arzneimittel-Forschung/Drug Research, 2003, vol. 53, # 1, p. 44 - 52

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Alapha-萘异氰酸酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 作用下， 生成 N-cinnamoyl-1-naphthylamine
  参考文献：
  名称：

  Angiotensin-Converting Enzyme Inhibitor Angioedema of the Intestine: A Case Report and Review of the Literature

  摘要：

  Visceral angioedema is a rare complication of angiotensin-converting enzyme (ACE) inhibitor use. To date, 15 cases have been reported in the literature. Common presentation is that of a middle-aged woman with abdominal pain, emesis, and diarrhea who has recently begun taking an ACE inhibitor. Signs include leukocytosis, ascites, and edematous small bowel seen on computed tomography. Diagnosis is elusive, and frequently invasive procedures, including surgery, are pursued. These can be avoided if the astute physician recognizes the association and withdraws the offending medication. We present the typical diagnostic dilemma faced in the evaluation of a patient with ACE inhibitor angioedema of the intestine, and review the current available literature.

  DOI：

  10.1097/00000441-200208000-00011

文献信息

• Selective Reduction of Quinolinones Promoted by a SmI₂/H₂O/MeOH System
  作者：Dengbing Xie、Songlin Zhang

  DOI：10.1021/acs.joc.2c00389

  日期：2022.7.1

  The selective reduction of quinolin-2(1H)-ones promoted by a SmI2/H2O/MeOH system is reported for the first time. The reaction is effectively carried out to afford 3,4-dihydroquinoline-2(1H)-ones under mild conditions in a one-pot fashion with good to excellent yields.

  首次报道了由 SmI 2 /H 2 O/MeOH 体系促进 quinolin-2(1 H )-ones的选择性还原。该反应在温和条件下以一锅法有效地进行，得到 3,4-二氢喹啉-2(1 H )-酮，产率从良好到优异。
• Palladium-catalyzed alkyne hydrocarbonylation under atmospheric pressure of carbon monoxide in the presence of hydrosilane
  作者：Yu Luo、Xilong Wang、Qianwen Liu、Yimiao He、Jing Li、Shuang Luo、Qiang Zhu

  DOI：10.1039/d2gc04689j

  日期：——

  which is performed under atmospheric pressure of CO in the absence of acids, has been developed. Palladium hydride (Pd-H) generated from triethylsilane (Et3SiH) rather than the traditionally used strong acid (HX) is applied for the first time in this transformation. In addition, an unusual counteranion-controlled linear and branch selectivity for terminal alkynes is observed under otherwise identical

  已经开发出一种用于炔烃烃基化的超温和反应条件，该反应条件是在 CO 大气压下在不存在酸的情况下进行的。由三乙基硅烷 (Et 3 SiH) 而不是传统上使用的强酸 (HX)生成的氢化钯 (Pd-H)首次应用于该转化中。此外，在其他相同条件下观察到不寻常的抗衡阴离子控制的末端炔烃的线性和支化选择性。广泛的 1,1-、1,2- 和 1,2,2-取代的 α,β-不饱和硫酯或酰胺可以区域选择性地从末端和内部炔烃中以中等到极好的收率获得。此外，当使用 2-(叔-丁基）- N -（2-炔基苯基）苯胺作为底物，在 TMS-SYNPHOS 作为手性配体存在下。
• The Triflic Acid-Mediated Cyclization Reactions of <i>N</i>-Cinnamoyl-1-Naphthylamines
  作者：Frank D. King、Abil E. Aliev、Stephen Caddick、Derek A. Tocher

  DOI：10.1021/jo4018827

  日期：2013.11.1

  N-Cinnamoyl-1-naphthylamines undergo a cyclization reaction with triflic acid to form 4-pheny1-3,4-dihydro-1H-naphth[1,8-bc] azepin-2- ones and 4-phenyl-3,4-dihydro-1H-benzo [It] quinolin-2-ones. However, the N-benzyl analogues also undergo a unique cascade reaction to form novel heptacyclic structures via a 1,2-addition followed by a 4-addition to the naphthalene. With an electron-rich N-benzyl substituent, the heptacycle is the sole product.
• Albrecht, Monatshefte fur Chemie, 1914, vol. 35, p. 1503
  作者：Albrecht

  DOI：——

  日期：——
• Palladium(II)-catalyzed regioselective carbonylative coupling of aniline derivatives with terminal aryl acetylenes to give acrylamides under syngas conditions
  作者：B. El Ali、A. El-Ghanam、M. Fettouhi、J. Tijani

  DOI：10.1016/s0040-4039(00)00899-6

  日期：2000.7

  The carbonylative coupling of aniline derivatives (la-h) with terminal aryl acetylenes (2a, b) catalyzed by Pd(OAc)(2) and 1,4-bis(diphenylphosphino)butane (dppb) under syngas conditions affords acrylamide derivatives 3 or 3' in excellent yields and selectivities. (C) 2000 Published by Elsevier Science Ltd.