1-甲基-4-(1-羟基乙基)萘 | 58149-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-甲基-4-(1-羟基乙基)萘
• 英文名称: 1-methyl-4-(1-hydroxyethyl)naphthalene
• 英文别名: 1-(4-methylnaphthalen-1-yl)ethan-1-ol；1-methyl-4-(1-hydroxy-ethyl)-naphthalene；1-(4-Methyl-1-naphthyl)-ethanol；1-(4-Methylnaphthalen-1-yl)ethanol
• CAS: 58149-67-0
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: BZCMVGFPXPZLBO-UHFFFAOYSA-N

物化性质

• 熔点：
  78.6 °C
• 沸点：
  333.7±11.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-甲基-4-(1-羟基乙基)萘 在 三溴化磷 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以91%的产率得到1-(1-Bromoethyl)-4-methylnaphthalene
  参考文献：
  名称：

  手性萘衍生物与单线态氧的非对映选择性[4 + 2]环加成中的取代基作用

  摘要：

  由1-溴-4-甲基萘制备了八种在立体异构中心具有各种官能团的手性衍生物1，其与单线态氧导致立体电子起源的取代基依赖性π-面选择性中的相应的内过氧化物2。

  DOI：

  10.1016/s0040-4039(00)73346-6
• 作为产物：
  描述：

  4-甲基-1-萘乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以94%的产率得到1-甲基-4-(1-羟基乙基)萘
  参考文献：
  名称：

  仲醇硅烷化中的取代基作用：机理研究

  摘要：

  已测量了由9-氮杂唑烷（TCAP）催化的CD4 3中的叔丁基二甲基甲硅烷基氯（TBSCl）使C4取代的1-（萘-1-基）乙醇底物甲硅烷基化的相对速率。所得选择性数据的Hammett图分析得出两个相交的线性相关性。对于供体取代的醇，观察到较小的正斜率ρ = + 0.09，而对于受体取代的醇，甲硅烷基化速率与负斜率稍大相关（ρ = -0.48）。4-（N，N）催化甲醇与TBSCl的反应。二甲基氨基）吡啶（DMAP）已在氯仿溶液中以几种不同的理论水平进行了研究。甲硅烷基化的DMAP与甲醇之间的甲硅烷基转移发生在极其平坦的表面上，几乎没有定义最小和过渡态。TBSCl与C4取代的1-（萘-1-基）乙醇化合物的路易斯碱和一般碱催化的反应机理的反应途径计算预测了这两种途径的紧密竞争。

  DOI：

  10.1002/chem.201803014

文献信息

• The Substituent Effect. X. Solvolysis of 3- and 4-Substituted 1-(1-Naphthylethyl) Chlorides
  作者：Yuho Tsuno、Masami Sawada、Takahiro Fujii、Yasuhide Yukawa

  DOI：10.1246/bcsj.48.3347

  日期：1975.11

  Fourteen 5-, 6-, and 7-substituted 1-(1-naphthylethyl) chlorides were prepared and the solvolysis rates were determined in 80% (v/v) aqueous acetone at 45 °C. The effects of −R substituents at respective positions were treated on the basis of the equation, logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+). The position dependency of the inductive effect was given by Cij(=ρi⁄ρi,4α); C3α=1.37, C4α=1.00, C5α=0.75

  制备了 14 种 5-、6- 和 7-取代的 1-(1-萘基乙基) 氯化物，并在 45 °C 下在 80% (v/v) 丙酮水溶液中测定溶剂分解速率。各位置-R取代基的影响按等式处理，logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+)。感应效应的位置依赖性由 Cij(=ρi⁄ρi,4α) 给出；C3α=1.37、C4α=1.00、C5α=0.75、C6α=0.57、C7α=0.72。Cij 值似乎与杜瓦的简化场函数 1/rij 相关。由比率 ρπ+⁄ρi,4α=qr·ij+ 给出的 Pi 电子效应的位置依赖性与 MO 指数的预测一致，例如 Forsyth 的 Δqij(ArCH2+ 参数。同样的处理也适用于其他三种萘反应性、脱氚、α-萘甲酸的 pKa 和萘基铵离子的 pKa。线性 ρi-ρi 关系在这些反应之间成立，表明感应传输的反应独立方案。qr·ij+ 值在共轭位置随
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  公开号：US20120220629A1

  公开（公告）日：2012-08-30

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• Asymmetric Transfer Hydrogenation of 1-Naphthyl Ketones by an <i>ansa</i>-Ru(II) Complex of a DPEN-SO₂N(Me)-(CH₂)₂(η⁶-<i>p</i>-Tol) Combined Ligand
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  DOI：10.1021/ol400393j

  日期：2013.4.5

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  作者：Waldemar Adam、Eva Maria Peters、Karl Peters、Michael Prein、Hans Georg von Schnering

  DOI：10.1021/ja00130a006

  日期：1995.6

  A series of chiral naphthyl alcohol derivatives 1 was prepared and submitted to sensitized photooxygenation. The corresponding endoperoxides 2 were formed in high yields through [4 + 2] cycloaddition of singlet oxygen. The pi-facial selectivity of singlet oxygen attack was determined and the stereochemistry of the product assigned for representative cases (1a,h) by X-ray analysis of the triols 3 derived from the endoperoxides by reduction. In the photooxygenation of the alcohols 1a-g in nonpolar solvents, the (alpha R*,1R*,4S*)-configurated endoperoxides 2a-g were formed preferentially (diastereomeric ratio (dr) greater than or equal to 85:15). Increase in solvent polarity or protection of the hydroxy group as the acetate in 1i or as the silyl ether in 1j led to substantial loss of diastereoselectivity. Placement of a methyl group at C2, as in alcohol 1h, gave high but opposite pi-facile selectivity (dr = 94:6), i.e., (alpha R*,1S*,4R*)-2h was formed as major product. The observed substitution effects on the pi-facial selectivity are rationalized in terms of steric and electronic control. Thus, hydrogen bonding operates between the unprotected hydroxy group and the incoming singlet oxygen dienophile. Peri strain leads to an effective energy discrimination of the respective diastereomeric transition states and, consequently, high pi-facial selectivities. An alkyl substituent at C2, however, induces additional ortho strain of 1,3-allylic origin, which overrides the effect of peri strain to afford highly selectively the opposite stereoisomer.
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  DOI：10.1021/ja00383a029

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