(1R,2R,4S,6R)-1-methyl-2-(4-methoxybenzyloxy)-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane | 1048013-51-9

• 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: (1R,2R,4S,6R)-1-methyl-2-(4-methoxybenzyloxy)-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane
• CAS: 1048013-51-9
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: UBVWGZNAULMYMY-HPBDAGMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  30.99
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,6R)-1-methyl-2-(4-methoxybenzyloxy)-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane 在 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以2.31 g的产率得到1-{(1R,3S,5R,6R)-6-methyl-5-(4-methoxybenzyloxy)-7-oxabicyclo[4.1.0]heptan-3-yl}ethanone
  参考文献：
  名称：

  An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer

  摘要：

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.

  DOI：

  10.1021/jo800876u
• 作为产物：
  描述：

  4-甲氧基溴苄 、 (1S,2R,4S,6R)-4-iso-propenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (1R,2R,4S,6R)-1-methyl-2-(4-methoxybenzyloxy)-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  An Improved Asymmetric Synthesis of Malyngamide U and Its 2′-Epimer

  摘要：

  An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of I and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.

  DOI：

  10.1021/jo800876u

文献信息

• Regio-and Stereoselective Ring Opening of Epoxides with Sodium Phenylselenide under Phase Transfer Conditions
  作者：Reginaldo Bezerra dos Santos、Valdemar Lacerda Junior、Paulo Roberto Zanotto、Timothy John Brocksom、Ursula Brocksom

  DOI：10.3184/030823408x282659

  日期：2008.1

  and trisubstituted epoxides with the phenylselenide anion under PTC conditions provides a simple, mild and efficient method for preparation of β-hydroxy phenylselenides with high regio- and stereoselectivity in yields from 67 to 98%. The reactions are carried out in aqueous NaOH/ THF using aminoiminomethanesulfinic acid (thiourea dioxide, TDO) to generate sodium phenylselenide from diphenyldiselenide

  在 PTC 条件下，多种单、二和三取代环氧化物与苯硒阴离子的开环反应为制备具有高区域和立体选择性的 β-羟基苯硒提供了一种简单、温和和有效的方法，产率从 67 到98%。该反应在NaOH/THF水溶液中使用氨基亚氨基甲亚磺酸（二氧化硫脲，TDO）进行以从二苯基二硒化物生成苯基硒化钠。