(1'S,3'R)-1-(3-hydroxy-1-methylbutoxy)-4-methylnaphthalene | 216008-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1'S,3'R)-1-(3-hydroxy-1-methylbutoxy)-4-methylnaphthalene
• 英文别名: (2R,4S)-4-(4-methylnaphthalen-1-yl)oxypentan-2-ol
• CAS: 216008-52-5
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: NPKZCBKGXKDQTD-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'S,3'R)-1-(3-hydroxy-1-methylbutoxy)-4-methylnaphthalene 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,6R)-1'-hydroperoxy-1',4,6-trimethylspiro[1,3-dioxane-2,4'-naphthalene]
  参考文献：
  名称：

  分子内醇用单线态氧氧化富电子萘过程中两性离子中间体的有效捕集

  摘要：

  在富电子萘与单线态氧的氧化过程中，两性离子中间体的存在通过亲核反应清洁有效地形成氢过氧化物得到澄清。

  DOI：

  10.1246/cl.1999.139
• 作为产物：
  描述：

  4-甲基-1-萘 、 (2R,4R)-pentanediol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(1'S,3'R)-1-(3-hydroxy-1-methylbutoxy)-4-methylnaphthalene
  参考文献：
  名称：

  Asymmetric Addition of an Electrophile to Naphthalenes Promoted and Stereodirected by Alcohol

  摘要：

  4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) reacts with 1 -methoxy-4-methylnaphthalene to give the 1,4-addition product in the presence of methanol; the reaction does not proceed in the absence of the alcohol. Methoxy exchange (with CD3OD) was also observed during the reaction. Reactions of PTAD with 1-(3-hydroxypropoxy)-4-methylnaphthalene and related naphthalenes afford stereoselectively 1,4-adducts (70-98% of the major diastereomer). The stereoface-selective addition of PTAD at C-4 with concurrent formation of an acetal at C-1 takes place in a syn manner, which is induced by the hydrogen-bonding interaction between PTAD and the hydroxy group. The alpha -methyl substitution on the propoxy side chain strongly enhances the stereodifferentiation (90% de) and accelerates the cyclization by the Thorpe-Ingold effect. The alkoxy moiety of the adduct is easily removed to give 4-methyl-4-amino-4H-naphthalen-1-one with high enantiomeric excess. The gamma -methyl group of the side chain also affects the stereodifferentiation. Thus, the two stereogenic centers of the (1S,3R)-3-hydroxy-1-methylbutoxy side chain work together to achieve the high stereodifferentiating 1,4-addition from the Si-Re face (up to 96% ee). Epimerization of the cyclic acetal of a minor adduct was observed during the reaction of 1-(3-hydroxybutoxy)-4-methylnaphthalene, indicating that the minor component of the final products is derived from the initial minor syn adduct formed from the opposite face. The syn selectivity of the addition is achieved completely in the initial stage of formation of both the major and the minor adducts.

  DOI：

  10.1021/ja0029477

文献信息

• Asymmetric Addition of an Electrophile to Naphthalenes Promoted and Stereodirected by Alcohol
  作者：Morifumi Fujita、Hironori Matsushima、Takashi Sugimura、Akira Tai、Tadashi Okuyama

  DOI：10.1021/ja0029477

  日期：2001.4.1

  4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) reacts with 1 -methoxy-4-methylnaphthalene to give the 1,4-addition product in the presence of methanol; the reaction does not proceed in the absence of the alcohol. Methoxy exchange (with CD3OD) was also observed during the reaction. Reactions of PTAD with 1-(3-hydroxypropoxy)-4-methylnaphthalene and related naphthalenes afford stereoselectively 1,4-adducts (70-98% of the major diastereomer). The stereoface-selective addition of PTAD at C-4 with concurrent formation of an acetal at C-1 takes place in a syn manner, which is induced by the hydrogen-bonding interaction between PTAD and the hydroxy group. The alpha -methyl substitution on the propoxy side chain strongly enhances the stereodifferentiation (90% de) and accelerates the cyclization by the Thorpe-Ingold effect. The alkoxy moiety of the adduct is easily removed to give 4-methyl-4-amino-4H-naphthalen-1-one with high enantiomeric excess. The gamma -methyl group of the side chain also affects the stereodifferentiation. Thus, the two stereogenic centers of the (1S,3R)-3-hydroxy-1-methylbutoxy side chain work together to achieve the high stereodifferentiating 1,4-addition from the Si-Re face (up to 96% ee). Epimerization of the cyclic acetal of a minor adduct was observed during the reaction of 1-(3-hydroxybutoxy)-4-methylnaphthalene, indicating that the minor component of the final products is derived from the initial minor syn adduct formed from the opposite face. The syn selectivity of the addition is achieved completely in the initial stage of formation of both the major and the minor adducts.
• Effective Trap of Zwitterionic Intermediate during Oxygenation of Electron-Rich Naphthalenes with Singlet Oxygen by the Intramolecular Alcohol
  作者：Morifumi Fujita、Masaki Ohshiba、Yayoi Yamasaki、Takashi Sugimura、Akira Tai

  DOI：10.1246/cl.1999.139

  日期：1999.2

  The presence of a zwitterionic intermediate during the oxygenation of electron-rich naphthalenes with singlet oxygen is clarified by the clean and efficient formation of hydroperoxide via nucleophi...

  在富电子萘与单线态氧的氧化过程中，两性离子中间体的存在通过亲核反应清洁有效地形成氢过氧化物得到澄清。