(7R,8S,10bS)-7,8-Dihydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one | 200638-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (7R,8S,10bS)-7,8-Dihydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one
• 英文别名: (7R,8S,10bS)-7,8-dihydroxy-1,5,6,7,8,9,10,10b-octahydro-[1,3]oxazolo[4,3-a]isoquinolin-3-one
• CAS: 200638-10-4
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: CEFXEQCPPUBRKJ-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (7R,8S,10bS)-7,8-Dihydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one 在 咪唑 、 三丁基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (7S,8S,10bS)-7-(2-Bromo-6-methoxyphenoxy)-8-[tert-butyl(dimethyl)silyloxy]-5,6,7,8,9,10-hexahydro-1H-oxazolo[4,3-a]isoquinolin-3-one
  参考文献：
  名称：

  Model Study for a General Approach to Morphine and Noroxymorphone via a Rare Heck Cyclization

  摘要：

  [GRAPHICS]beta-Bromoethylbenzene was converted to the pentacycle 6 in 11 steps. The key features of this model were the toluene dioxygenase catalyzed production of diol 13 and the stereospecific Heck closure of 5 to 6.

  DOI：

  10.1021/ol991135g
• 作为产物：
  描述：

  (5S,6S)-5,6-Di(benzoyloxy)-1-(2-bromoethyl)cyclohex-1-ene 在 lithium hydroxide 、 sodium tetrahydroborate 、 1,1,2,3-四甲基胍 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (7R,8S,10bS)-7,8-Dihydroxy-1,5,6,7,8,9,10,10b-octahydro-oxazolo[4,3-a]isoquinolin-3-one
  参考文献：
  名称：

  Model Study for a General Approach to Morphine and Noroxymorphone via a Rare Heck Cyclization

  摘要：

  [GRAPHICS]beta-Bromoethylbenzene was converted to the pentacycle 6 in 11 steps. The key features of this model were the toluene dioxygenase catalyzed production of diol 13 and the stereospecific Heck closure of 5 to 6.

  DOI：

  10.1021/ol991135g

文献信息

• Chemoenzymatic synthesis of the morphine skeleton via radical cyclization and a C10C11 closure
  作者：Gabor Butora、Tomas Hudlicky、Stephen P. Fearnley、Andrew G. Gum、Michele R. Stabile、Khalil Abboud

  DOI：10.1016/0040-4039(96)01867-9

  日期：1996.11

  A short synthesis of a morphinan skeleton has been accomplished. The key steps involve enzymatic dihydroxylation of β-bromoethyl benzene, vinyl and aryl radical cyclizations, and Friedel-Crafts closure of an aziridinium ion or an acid-catalyzed closure of an aldehyde to form the C10C11 bond.

  吗啡骨架的简短合成已完成。的关键步骤涉及β溴乙基苯，乙烯基的酶促二羟基和芳基的环化反应，以及吖丙啶鎓离子或醛的酸催化闭合的Friedel-Crafts闭合以构成C 10 C 11键。
• Model Study for a General Approach to Morphine and Noroxymorphone via a Rare Heck Cyclization
  作者：Dean A. Frey、Caiming Duan、Tomas Hudlicky

  DOI：10.1021/ol991135g

  日期：1999.12.1

  [GRAPHICS]beta-Bromoethylbenzene was converted to the pentacycle 6 in 11 steps. The key features of this model were the toluene dioxygenase catalyzed production of diol 13 and the stereospecific Heck closure of 5 to 6.