(+/-)-2-chloroacetoxy-2'-hydroxy-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-2-chloroacetoxy-2'-hydroxy-1,1'-binaphthyl
• 英文别名: [1-(2-hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-chloroacetate
• 化学式: C₂₂H₁₅ClO₃
• 分子量: 362.812
• InChiKey: KVRULGUYNRCNDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氯乙酸酐 、 S-1,1'-联-2-萘酚 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以15%的产率得到(+/-)-2-chloroacetoxy-2'-hydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  Inagaki, Minoru; Hiratake, Jun; Nishioka, Takaaki, Agricultural and Biological Chemistry, 1989, vol. 53, # 7, p. 1879 - 1884

  摘要：

  DOI：

文献信息

• Catalytic conjugate addition promoted by the copper(I)–monothiobinaphthol system. Part 2.1 Optimal ligand synthesis and initial catalytic results
  作者：Shamsudin M. Azad、Simon M. W. Bennett、Stephen M. Brown、Jason Green、Ekkehard Sinn、Chris M. Topping、Simon Woodward

  DOI：10.1039/a605620b

  日期：——

  Both racemic and (Ra)-1,1′-bi-2-naphthol react with Bu2SnO to provide an O,O-stannylene acetal which opens with Me2NC(S)Cl or RC(O)Cl [R = Ph, CCl3, OPr, 1-C10H7, 2-C10H7, SMe, CH2Cl and (-)-menthyl] to fashion monoacylated derivatives. Two of the products, 2-(N,N-dimethylthiocarbamoyloxy)-2′-hydroxy-1,1 ′-binaphthyl 6 and 2-hydroxy-2′-[(1R,3S,5R)-menthylcarbon yloxy]-1,1′-binaphthyl 14, have been crystallographically characterised. The former is converted to 2-(N,N-dimethylcarbamoyloxy)-2′-(N, N-dimethylthiocarbamoyloxy)-1,1′-binaphthyl 15 with Me2NC(O)Cl. This compound is directly available from 1,1′-bi-2-naphthol via a one-pot sequential reaction with Me2NC(S)Cl and Me2NC(O)Cl under NEt3–DMAP catalysis. Thermolysis of 15 followed by hydrolysis provides an efficient preparation of 2-hydroxy-2′-mercapto-1,1′-binaphthyl 3 (monothiobinaphthol). In the presence of [Cu(MeCN)4]BF4, 3 leads to a highly efficient catalyst for the 1,4-addition of BuLi and RMgX (R = Me, Bu, Ph; X = Cl, Br) to cyclic enones.

  无论是消旋的还是(R)-1,1'-双-2-萘酚都能与Bu2SnO反应，形成O,O'-锡烯缩醛，该缩醛可以与Me2NC(S)Cl或RC(O)Cl [R = Ph, CCl3, OPr, 1-C10H7, 2-C10H7, SMe, CH2Cl和(-)-menthyl]反应生成单酰化的衍生物。其中两种产物，即2-(N,N-二甲基硫代氨基甲酰氧基)-2'-羟基-1,1'-联萘6和2-羟基-2'-[(1R,3S,5R)-menthyl碳酸酯氧基]-1,1'-联萘14，已经通过晶体学进行了表征。前者可以被Me2NC(O)Cl转化为2-(N,N-二甲基氨基甲酰氧基)-2'-(N,N-二甲基硫代氨基甲酰氧基)-1,1'-联萘15。该化合物可以直接通过1,1'-双-2-萘酚与Me2NC(S)Cl和Me2NC(O)Cl在NEt3-DMAP催化下的一锅顺序反应制备。15的热分解和随后水解提供了高效制备2-羟基-2'-巯基-1,1'-联萘3 (单硫代联萘酚)的方法。在[Cu(MeCN)4]BF4的存在下，3可以作为催化剂，高效地催化BuLi和RMgX (R = Me, Bu, Ph; X = Cl, Br)对环状烯酮的1,4-加成反应。
• Inagaki, Minoru; Hiratake, Jun; Nishioka, Takaaki, Agricultural and Biological Chemistry, 1989, vol. 53, # 7, p. 1879 - 1884
  作者：Inagaki, Minoru、Hiratake, Jun、Nishioka, Takaaki、Oda, Jun'ichi

  DOI：——

  日期：——