optically inactive 2-acetoxy-3-phenyl-butane | 58577-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: optically inactive 2-acetoxy-3-phenyl-butane
• 英文别名: Opt.-inakt. 2-Acetoxy-3-phenyl-butan；3-phenylbutan-2-yl acetate
• CAS: 58577-62-1
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: RRPZBUZEYVUSEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  optically inactive 2-acetoxy-3-phenyl-butane 生成 反式-2-苯基-2-丁烯
  参考文献：
  名称：

  Ionic Polymerization. Reactions of α-Ethylstyrene and cis- and trans-α,β-Dimethylstyrene with Stannic Chloride¹

  摘要：

  DOI：

  10.1021/ja01540a064
• 作为产物：
  描述：

  3-phenyl-2-butanol 、 乙酸酐 在 4-二甲氨基吡啶 、 sodium carbonate 作用下， 以 乙酸乙酯 为溶剂， 生成 optically inactive 2-acetoxy-3-phenyl-butane
  参考文献：
  名称：

  Enantiopreference of Lipase from Pseudomonas cepacia toward Primary Alcohols

  摘要：

  We propose an empirical rule that predicts which enantiomer of a primary alcohol reacts faster in reactions catalyzed by lipase from Pseudomonas cepacia (PCL). This rule, based on the size of the substituents at the stereocenter, shows an 89% reliability (correct for 54 of 61 examples). This rule is not reliable for primary alcohols that have an oxygen atom attached to the stereocenter; we excluded these alcohols from the tally above. Surprisingly, the sense of enantiopreference of PCL toward primary alcohols is opposite to its enantiopreference toward secondary alcohols. That is, the OH of secondary alcohols and the CH2OH of primary alcohols point in opposite directions. We suggest, however, that this opposite orientation does not imply a different position of the substituents in the active site of the lipase. Instead, PCL accommodates the extra CH2 in primary alcohols as a kink between the stereocenter and the oxygen which allows a similar position of the alcohol oxygen in both. We tried to increase the enantioselectivity of PCL toward primary alcohols by increasing the difference in the size of the substituents but did not find a consistent increase in enantioselectivity. We suggest that high enantioselectivity toward primary alcohols requires not only a significant difference in the size of the substituents, but also control of the conformation along the C(1)-C(2) bond.

  DOI：

  10.1021/jo00126a056

文献信息

• Enantioselectivity and diastereoselectivity in the hydrolysis of acylals and structurally related esters of secondary alcohols with Candida rugosa lipase
  作者：Yiannis S. Angelis、Ioulia Smonou

  DOI：10.1016/s0040-4039(98)00256-1

  日期：1998.4

  Comparative studies of enantioselectivities and diastereoselectivities in the hydrolysis reactions of acylals and 50:50 threo-erythro mixtures of the esters of related secondary alcohols with Candida rugosa lipase gave significant information about the reactivity order in the enzymatic hydrolysis of acylals.

  对酰基和相关仲醇的酯与皱纹假丝酵母脂肪酶的50:50的苏-赤混合物的水解反应中的对映选择性和非对映选择性的比较研究提供了有关酰基酶水解反应顺序的重要信息。
• Un nouvel aspect de la reactivite des trihalogenomethyltrialkyletains: l'addition aux aldehydes
  作者：Christian Furet、Christian Servens、Michel Pereyre

  DOI：10.1016/s0022-328x(00)89386-9

  日期：1975.12

  Trichloromethyl- and tribromomethyl-tributyltin give adducts with aldehydes. On acidolysis the corresponding trichloromethyl- and tribromomethylcarbinols are obtained in good yields. The stereochemistry of the addition reaction with hydratropic aldehyde was investigated and the substituent effects were determined by means of competitive experiments with substituted benzaldehydes. The inefficiency of

  三氯甲基-和三溴甲基-三丁基锡与醛形成加合物。在酸解中，以良好的产率获得相应的三氯甲基和三溴甲基甲醇。研究了与亲水醛加成反应的立体化学，并通过竞争性实验确定了取代苯甲醛的取代基效果。自由基反应引发剂和抑制剂的效率低下，再加上不存在重排产物，似乎排除了自由基的作用机理。该反应可能是离子性的，并且羰基上三卤甲基的亲核攻击。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Comp.12, 1.4.1.1.1.5.2.1.7, page 69 - 97
  作者：

  DOI：——

  日期：——
• Kinoshita, Tomomi; Takemoto, Masaki; Shibayama, Koichi, Journal of Chemical Research, Miniprint, 1993, # 8, p. 2153 - 2174
  作者：Kinoshita, Tomomi、Takemoto, Masaki、Shibayama, Koichi、Takeuchi, Ken'ichi

  DOI：——

  日期：——