2-tert-butyl-dimethylsilyloxymethyl-6-methyl phenol | 185302-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-tert-butyl-dimethylsilyloxymethyl-6-methyl phenol
• 英文别名: 2-[[Tert-butyl(dimethyl)silyl]oxymethyl]-6-methylphenol
• CAS: 185302-70-9
• 化学式: C₁₄H₂₄O₂Si
• 分子量: 252.429
• InChiKey: RUDLYTZGISBJGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2-tert-butyl-dimethylsilyloxymethyl-6-methyl phenol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二甲酸二异丙酯 、 氟化氢吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2R)-ethyl 2-(2’-bromomethyl-6’-methylphenoxy)propanoate
  参考文献：
  名称：

  Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C–O Axis

  摘要：

  A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.

  DOI：

  10.1021/ja4018122
• 作为产物：
  描述：

  邻甲酚 在 咪唑 、 sodium tetrahydroborate 、 三乙胺 、 magnesium chloride 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.25h， 生成 2-tert-butyl-dimethylsilyloxymethyl-6-methyl phenol
  参考文献：
  名称：

  Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C–O Axis

  摘要：

  A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.

  DOI：

  10.1021/ja4018122

文献信息

• Chiral synthesis of (+)-8′-demethyl abscisic acid
  作者：Patricia A. Rose、Bo Lei、Angela C. Shaw、Suzanne R. Abrams、M. K. Walker-Simmons、Scott Napper、J. Wilson Quail

  DOI：10.1139/v96-205

  日期：1996.10.1

  An enantioselective synthesis of (+)-8′-demethyl ABA (2) is described. The chiral intermediate 7 was prepared by yeast reduction of a substituted monoprotected cyclohexa-2,5-dien-1,4-dione (9) synthesized through a phenol oxidation. The scope and limitations of the phenol oxidation is described. 8′-Demethyl ABA shows ABA-like activity in wheat embryo germination inhibition, showing that the 8′-methyl group is not essential for biological activity. Key words: abscisic acid, phenol oxidation, yeast reduction.

  一个选择性合成(+)-8'-去甲基ABA (2)的手性合成方法被描述。手性中间体7是通过酵母还原经酚氧化合成的取代单保护的环己二烯-1,4-二酮(9)制备的。描述了酚氧化的范围和限制。8'-去甲基ABA在小麦胚芽发芽抑制中显示出类似ABA的活性，表明8'-甲基基团对生物活性并非必要。关键词：脱落酸，酚氧化，酵母还原。
• Retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：US05905068A1

  公开（公告）日：1999-05-18

  A compound of the formula: ##STR1## is disclosed as a retroviral protease inhibitor compound. Also disclosed are methods and compositions for inhibiting an HIV infection.

  一种化合物的化学式为：##STR1##，被披露为一种逆转录病毒蛋白酶抑制剂化合物。还披露了用于抑制HIV感染的方法和组合物。
• Asymmetric Induction via Short-Lived Chiral Enolates with a Chiral C–O Axis
  作者：Tomoyuki Yoshimura、Keisuke Tomohara、Takeo Kawabata

  DOI：10.1021/ja4018122

  日期：2013.5.15

  A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be similar to 1 s at -78 degrees C.