(7R)-3,5-dimethoxy<7-2H1>benzyl alcohol | 86728-51-0

• 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: (7R)-3,5-dimethoxy<7-2H1>benzyl alcohol
• 英文别名: (7R)-3,5-dimethoxy<7-²H1>benzyl alcohol；3,5-Dimethoxy-(7R)-<7-(2)H>benzyl alcohol；3,5-Dimethoxy-(7R)-(7-(2)H)benzyl alcohol
• CAS: 86728-51-0
• 化学式: C₉H₁₂O₃
• 分子量: 169.185
• InChiKey: AUDBREYGQOXIFT-MUFQJMLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 在 <9-(2)H>-9-BBN 、 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(7R)-3,5-dimethoxy<7-2H1>benzyl alcohol
  参考文献：
  名称：

  A simple and efficient synthesis of chiral acetic acid of high optical purity

  摘要：

  DOI：

  10.1021/jo00168a027

文献信息

• Cryptic stereochemistry of berberine alkaloid biosynthesis
  作者：Jeffrey A. Bjorklund、Thomas Frenzel、Martina Rueffer、Motomasa Kobayashi、Ursula Mocek、Christina Fox、John M. Beale、Stefan Groeger、Meinhart H. Zenk、Heinz G. Floss

  DOI：10.1021/ja00110a009

  日期：1995.2

  The cryptic stereochemistry of one-carbon transformations in berberine biosynthesis has been elucidated by the chiral methyl group methodology and tritium NMR spectroscopy. The transfer of the methyl group of AdoMet to oxygen and nitrogen occurs with complete inversion of configuration. The oxidative formation of the berberine bridge from the N-methyl group of reticuline involves removal of a methyl hydrogen with a primary kinetic isotope effect k(H)/k(D) = 4.0 and its replacement by the phenyl group in an inversion mode. The subsequent aromatization catalyzed by (S)-tetrahydroprotoberberine oxidase (STOX) involves nonstereospecific hydrogen removal from C-8 with little or no isotope effect. In the formation of the methylenedioxy bridge, a hydrogen is removed from the methoxy group with k(H)/k(D) > 5 and replaced by the adjacent phenolic oxygen with apparent retention, accompanied by substantial racemization. The subsequent reductive opening of the methylenedioxy bridge of berberine to the methoxy group of jatrorrhizine proceeds stereospecifically, apparently in an inversion mode. Mechanistic interpretations of these findings are discussed.
• KOBAYASHI, KOJI;JADHAV, P. K.;ZYDOWSKY, T. M.;FLOSS, H. G., J. ORG. CHEM., 1983, 48, N 20, 3510-3512
  作者：KOBAYASHI, KOJI、JADHAV, P. K.、ZYDOWSKY, T. M.、FLOSS, H. G.

  DOI：——

  日期：——