1-(4-Butyloxy-phenyl)-ethanol-(1) | 91763-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-Butyloxy-phenyl)-ethanol-(1)
• 英文别名: 1-(4-n-Butoxyphenyl)ethanol；1-(4-butoxyphenyl)ethanol
• CAS: 91763-92-7
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: BPCDNYDWSDNPJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-(4-Butyloxy-phenyl)-ethanol-(1) 在 草酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 生成 5-[1-(4-Butoxyphenyl)ethyl]-6-methoxy-1,3-benzodioxole
  参考文献：
  名称：

  In vivo antitumor activity of 6-benzyl-1,3-benzodioxole derivatives against the P388, L1210, B16, and M5076 murine models

  摘要：

  A series of 6-benzyl-1,3-benzodioxoles have been synthesized and evaluated against the in vivo ip P388 murine lymphocytic leukemia. Selected activities against this system were tested against the additional in vivo systems L1210, B16, M5076, and MX1. The most active of the 6-benzyl-1,3-benzodioxoles tested were as effective as podophyllotoxin as experimental antitumor agents in vivo, but larger doses were required. Three of the P388-active series members were active against the in vitro astrocytoma assay, which detects compounds that interfere with or bind to tubulin.

  DOI：

  10.1021/jm00393a012
• 作为产物：
  描述：

  4-(正丁氧基)苯乙酮 在 硼酸三甲酯 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以99%的产率得到1-(4-Butyloxy-phenyl)-ethanol-(1)
  参考文献：
  名称：

  温度对恶唑硼烷催化的酮不对称还原的对映选择性的影响。非催化硼烷还原，在还原体系中不可忽略的因素。

  摘要：

  使用具有各种官能团的烷基芳基酮和衍生自硼酸三甲酯和（S）-α，α-二苯基脯氨酸的B-甲氧基恶唑硼烷仔细研究了温度对恶唑硼烷催化的不对称硼烷还原酮的对映选择性的影响。作为催化剂。在有或没有催化剂的情况下，在THF和甲苯中的一定温度范围内进行还原。通过GC分析确定酮向醇的转化率，还原速率随着有或没有催化剂的反应温度的升高而增加。但是，催化还原的速率比没有催化剂的速率增加得更快。结果表明，非催化硼烷还原是还原中对映选择性的重要因素。

  DOI：

  10.1021/jo035203v

文献信息

• DMSO-catalyzed chlorination of alcohols using N-phenylbenzimidoyl chloride
  作者：Qiang Wang、Jian Xu、Zhou-Qing Xu、Ji-Dan Yan

  DOI：10.1007/s11164-012-0738-z

  日期：2013.5

  N-phenylbenzimidoyl chloride has been demonstrated as an efficient chlorination reagent catalyzed by dimethyl sulfoxide (DMSO) in conversion of alcohols to corresponding chlorides. The reaction conditions were mild, and most of the substrates gave satisfactory yields. The configuration inversion of the chlorination was proved using optically active phenyl alcohols. The amount of DMSO can be as low as

  N-苯基苯甲酰氯已被证明是由二甲亚砜（DMSO）催化的高效氯化试剂，可将醇转化为相应的氯化物。反应条件温和，并且大多数底物给出令人满意的产率。使用旋光性苯醇证明了氯化的构型转化。在不降低氯化效率的情况下，DMSO的量可以低至0.001当量。提出了合理的反应机理，并通过实验证明。该反应在伯苄醇，仲苄醇和未活化的脂族醇中是立体选择性的，并且可能是化学选择性的。
• Chemoselective Etherification of Benzyl Alcohols Using 2,4,6-Trichloro-1,3,5-triazine and Methanol or Ethanol Catalyzed by Dimethyl Sulfoxide
  作者：Chunbao Li、Lili Sun、Yuping Guo、Guisheng Peng

  DOI：10.1055/s-0028-1083184

  日期：——

  An efficient method for the transformation of benzyl alcohols into their methyl or ethyl ethers has been established using 2,4,6-trichloro-1,3,5-triazine (TCT) and dimethyl sulfoxide in methanol or ethanol. This procedure chemoselectively converts benzylic hydroxys into their methyl or ethyl ethers in the presence of aliphatic or phenolic hydroxys.

  一种高效的方法已利用2,4,6-三氯-1,3,5-三嗪（TCT）与二甲基亚砜在甲醇或乙醇中的反应，实现了苄醇向其甲基或乙基醚的转化。该方法能在脂肪族或酚羟基存在下，化学选择性地将苄位羟基转化为甲基或乙基醚。
• ROHMANN; MEISEL, Archiv der Pharmazie, 1961, vol. 294 /66, p. 538 - 549
  作者：ROHMANN、MEISEL

  DOI：——

  日期：——
• Effect of Temperature on the Enantioselectivity in the Oxazaborolidine-Catalyzed Asymmetric Reduction of Ketones. Noncatalytic Borane Reduction, a Nonneglectable Factor in the Reduction System
  作者：Xu、Wei、Zhang

  DOI：10.1021/jo035203v

  日期：2003.12.1

  The effect of temperature on the enantioselectivity of the oxazaborolidine-catalyzed asymmetric borane reduction of ketones has been investigated carefully using alkyl aryl ketones with a variety of functional groups and a B-methoxyoxazaborolidine derived from trimethyl borate and (S)-alpha,alpha-diphenylprolinol as a catalyst. The reductions were carried out over a range of temperatures in THF and

  使用具有各种官能团的烷基芳基酮和衍生自硼酸三甲酯和（S）-α，α-二苯基脯氨酸的B-甲氧基恶唑硼烷仔细研究了温度对恶唑硼烷催化的不对称硼烷还原酮的对映选择性的影响。作为催化剂。在有或没有催化剂的情况下，在THF和甲苯中的一定温度范围内进行还原。通过GC分析确定酮向醇的转化率，还原速率随着有或没有催化剂的反应温度的升高而增加。但是，催化还原的速率比没有催化剂的速率增加得更快。结果表明，非催化硼烷还原是还原中对映选择性的重要因素。
• In vivo antitumor activity of 6-benzyl-1,3-benzodioxole derivatives against the P388, L1210, B16, and M5076 murine models
  作者：Leonard Jurd、V. L. Narayanan、Kenneth D. Paull

  DOI：10.1021/jm00393a012

  日期：1987.10

  A series of 6-benzyl-1,3-benzodioxoles have been synthesized and evaluated against the in vivo ip P388 murine lymphocytic leukemia. Selected activities against this system were tested against the additional in vivo systems L1210, B16, M5076, and MX1. The most active of the 6-benzyl-1,3-benzodioxoles tested were as effective as podophyllotoxin as experimental antitumor agents in vivo, but larger doses were required. Three of the P388-active series members were active against the in vitro astrocytoma assay, which detects compounds that interfere with or bind to tubulin.