methyl 1-vinyl-3-naphthoate | 331281-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1-vinyl-3-naphthoate
• 英文别名: Methyl 4-ethenylnaphthalene-2-carboxylate
• CAS: 331281-95-9
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: PAOLWWGAOGJWPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1-vinyl-3-naphthoate 在 sodium tetrahydroborate 、 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 sodium hydride 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 4-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 5. Design, Synthesis, and SAR of a Highly Potent Inhibitor Series

  摘要：

  A highly potent AMP deaminase (AMPDA) inhibitor series was discovered by replacing the N3 substitutents of the two lead AMPDA inhibitor series with a conformationally restricted group. The most potent compound, 3-[2-(3-carboxy-4-bromo-5,6,7,8-tetrahydroaphthyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (24b), represents a 10- to 250-fold enhancement in AMPDA inhibitory potency without loss in the enzyme specificity. The potency of the inhibitor 24b (AMPDA K-i = 0.002 muM) is 10(5)-fold lower than the K-m for the substrate AMP. It represents the most potent nonnucleotide AMPDA inhibitor known.

  DOI：

  10.1021/jm000355t
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以68%的产率得到methyl 1-vinyl-3-naphthoate
  参考文献：
  名称：

  Controlled synthesis of 1-vinylnaphthalenes versus (E)-α-(1,3-enyn-4-yl)-α,β-unsaturated esters from Morita–Baylis–Hillman bromides: a sequential alkynylation and competitive 6π-electrocyclization versus conjugative transposition of a triple bond

  摘要：

  An expedient controlled synthesis of 1-vinylnaphthalenes and various dienyne derivatives has been carried out from the Morita-Baylis-Hillman bromides and propargyl acetate or p-nitrophenyl propargyl ether. By judicious choice of base, reaction temperature, and leaving group, a selective synthesis of 1-vinylnaphthalenes and dienynes, (E)-alpha-(1,3-enyn-4-yl)-alpha,beta-unsaturated esters, could be performed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.007

文献信息

• Controlled synthesis of 1-vinylnaphthalenes versus (E)-α-(1,3-enyn-4-yl)-α,β-unsaturated esters from Morita–Baylis–Hillman bromides: a sequential alkynylation and competitive 6π-electrocyclization versus conjugative transposition of a triple bond
  作者：Jin Woo Lim、Ko Hoon Kim、Se Hee Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2013.03.007

  日期：2013.5

  An expedient controlled synthesis of 1-vinylnaphthalenes and various dienyne derivatives has been carried out from the Morita-Baylis-Hillman bromides and propargyl acetate or p-nitrophenyl propargyl ether. By judicious choice of base, reaction temperature, and leaving group, a selective synthesis of 1-vinylnaphthalenes and dienynes, (E)-alpha-(1,3-enyn-4-yl)-alpha,beta-unsaturated esters, could be performed. (C) 2013 Elsevier Ltd. All rights reserved.
• AMP Deaminase Inhibitors. 5. Design, Synthesis, and SAR of a Highly Potent Inhibitor Series
  作者：Srinivas Rao Kasibhatla、Brett C. Bookser、Wei Xiao、Mark D. Erion

  DOI：10.1021/jm000355t

  日期：2001.2.1

  A highly potent AMP deaminase (AMPDA) inhibitor series was discovered by replacing the N3 substitutents of the two lead AMPDA inhibitor series with a conformationally restricted group. The most potent compound, 3-[2-(3-carboxy-4-bromo-5,6,7,8-tetrahydroaphthyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (24b), represents a 10- to 250-fold enhancement in AMPDA inhibitory potency without loss in the enzyme specificity. The potency of the inhibitor 24b (AMPDA K-i = 0.002 muM) is 10(5)-fold lower than the K-m for the substrate AMP. It represents the most potent nonnucleotide AMPDA inhibitor known.