1-(p-methoxyphenyl)ethanol-2,2,2-d3 | 75295-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(p-methoxyphenyl)ethanol-2,2,2-d3
• 英文别名: 4-methoxy-α-trideuteriomethyl-benzyl alcohol；2,2,2-Trideuterio-1-(4-methoxyphenyl)ethanol
• CAS: 75295-98-6
• 化学式: C₉H₁₂O₂
• 分子量: 155.169
• InChiKey: IUUULXXWNYKJSL-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(p-methoxyphenyl)ethanol-2,2,2-d3 在 五氟化锑 、 氟磺酸 作用下， 以 various solvent(s) 为溶剂， 生成
  参考文献：
  名称：

  Deuterium isotope effects on the carbon-13 chemical shifts of carbocations

  摘要：

  DOI：

  10.1021/ja00544a010
• 作为产物：
  描述：

  p-methoxyacetophenone-2,2,2-d3 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-(p-methoxyphenyl)ethanol-2,2,2-d3
  参考文献：
  名称：

  Effects of deuterium substitution on the rates of organic reactions. XI. .alpha.- and .beta.-Deuterium effects on the solvolysis rates of a series of substituted 1-phenylethyl halides

  摘要：

  DOI：

  10.1021/ja01004a037

文献信息

• Mechanism of the [2 + 2] Photocycloaddition of Fullerene C₆₀ with Styrenes
  作者：Georgios Vassilikogiannakis、Maria Hatzimarinaki、Michael Orfanopoulos

  DOI：10.1021/jo0006223

  日期：2000.12.1

  op-1-ene-3,3,3-d(3) (trans-5-d(3)) to C(60) is attributed to a steric kinetic isotope effect (k(H)/k(D) = 0.78). The loss of stereochemistry in the cyclobutane ring excludes a concerted addition and is consistent with a stepwise mechanism. Intermolecular secondary kinetic isotope effects of the [2 + 2] photocycloaddition of 3-d(0) vs 3-d(1), and 3-d(6) as well as 5-d(0) vs 5-d(1), and 5-d(6) to C(60)

  立体化学研究[2 + 2]光加成的顺式/反式-4-丙烯基茴香醚（顺式-1和反式1）和顺式-1-（对甲氧基苯基）乙烯-2-d（1）（顺式-3- d（1））到C（60）在前者中表现出立体特异性，而反式2环加合物表现出立体选择性。在光化学添加（E）-1-（对甲氧基苯基）-2-甲基-丙氧基的情况下，观察到的立体选择性有利于cis-6-d（3）[2 + 2]非对映异构体12％。 C（60）的1-ene-3,3,3-d（3）（trans-5-d（3））归因于空间动力学同位素效应（k（H）/ k（D）= 0.78） 。环丁烷环中立体化学的损失排除了一致的加成，并且与逐步机理一致。3-d（0）与3-d（1）和3-d（6）以及5-d（0）与5-d（1）的[2 + 2]光环加成的分子间二级动力学同位素效应），还测量了5-d（6）至C（60）。由于两个乙烯基氢在3的β-碳原子上被氘取代而引起的分子间竞争表现出实质性的反向α-次级同位素效应k（H）/
• The Ei Reaction of Substituted<i>threo</i>- and<i>erythro</i>-1-Phenylethyl Phenyl Sulfoxides
  作者：Toshiaki Yoshimura、Eiichi Tsukurimichi、Yukihiko Iizuka、Hironobu Mizuno、Hiroshi Isaji、Choichiro Shimasaki

  DOI：10.1246/bcsj.62.1891

  日期：1989.6

  Substituted (RS,SR)-1-phenylethyl phenyl sulfoxides (threo) (XC6H4S(O)CH(CH3)C6H4Y) and some substituted (RR,SS)-sulfoxides (erythro) were prepared and kinetic investigation for the thermal decomposition was carried out at 80.0, 90.0, and 100.0 °C in dioxane. Hammett plots for threo-XC6H4S(O)CH(CH3)C6H5 gave positive ρ-values (ρX=0.60–0.64 at three temperatures), while those for threo- and erythro

  制备了取代的 (RS,SR)-1-苯乙基苯基亚砜 (threo) (XC6H4S(O)CH(CH3)C6H4Y) 和一些取代的 (RR,SS)-亚砜 (erythro) 并进行了热分解动力学研究在二恶烷中分别在 80.0、90.0 和 100.0 °C 下进行测试。苏式-XC6H4S(O)CH(CH3)C6H5 的哈米特图给出了正 ρ 值（三种温度下的 ρX=0.60–0.64），而苏式和赤式 C6H5S(O)CH(CH3)C6H4Y 的哈米特图给出了正的 ρ 值（ρX=0.60–0.64）尽管取代基的影响很小，但在 m-OCH3 取代基处形成带有底部的线条。同时，在所有温度下都观察到苏-和赤-C6H5S(O)CH(CD3)C6H4Y（Y=H，p-OMe，m-Cl）（kH⁄kD=4-6）的大动力学同位素效应。所有亚砜的活化能在 104-121 kJ mol-1 的范围内，而激活熵相对较大（7-37
• Solvolysis of 1-alkyl-1-chloro-1-(4-methyl)phenylmethanes. Nucleophilic solvent intervention and extendedYBnCl scale
  作者：Kwang-Ting Liu、Lih-Wie Chang、Der-Gann Yu、Png-Shao Chen、Ju-Ta Fan

  DOI：10.1002/(sici)1099-1395(199712)10:12<879::aid-poc879>3.0.co;2-k

  日期：1997.12

  The solvolysis of 1-alkyl-1-chloro-1-(4-methyl)phenylmethanes (4a-d) in aqueous acetone, aqueous ethanol, aqueous methanol and ethanol-trifluoroethanol was studied. Grunwald-Winstein-type correlation analysis using the Y-BnCl scale suggests significant nucleophilic solvent intervention in the ease of 1-chloro-1-(4-methyl)phenylethane (4a). Increasing bulkiness of the 1-alkyl substituent from methyl (4a) to ethyl (4b), to isopropyl (4c) and to tert-butyl (4d) resulted in a gradual change to limiting S(N)1 mechanisms. The observed excellent linear correlations with Y-BnCl and the good solubility in high-water-containing binary solvents made 4d a suitable reference standard For deriving more Y-BnCl values. A positive azide salt effect was realized in the solvolysis of 4a but not 4d. A small decrease in the beta-deuterium kinetic Isotope effect from 4a to 1-chloro-1-(4-methoxyphenyl)propane (5) suggested the presence of additional stabilization of the benzylic cationic transition state. However, no relationship between k(CH3)/k(CD3) and the solvent effect was found. The superiority of employing the Y-BnCl scale over the combination of Y-Cl and I scales in the mehanistic study was observed. (C) 1997 John Wiley & Sons, Ltd.
• Effects of deuterium substitution on the rates of organic reactions. XI. .alpha.- and .beta.-Deuterium effects on the solvolysis rates of a series of substituted 1-phenylethyl halides
  作者：V. J. Shiner、W. E. Buddenbaum、B. L. Murr、G. Lamaty

  DOI：10.1021/ja01004a037

  日期：1968.1
• Stereochemistry and Isotope Effects of the [2 + 2] Photocycloadditions of Arylalkenes to C₆₀. A Stepwise Mechanism
  作者：Georgios Vassilikogiannakis、Michael Orfanopoulos

  DOI：10.1021/ja970916e

  日期：1997.8.1