(+)-(1R,2S)-1,2-epoxy-1,2-dihydroacridine | 159700-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+)-(1R,2S)-1,2-epoxy-1,2-dihydroacridine
• 英文别名: (1R,2S)-(+)-1,2-Epoxy-1,2-dihydroacridine；(1R,2S)-acridine-1,2-oxide；Acridine 1,2-oxide；(1aS,9bR)-1a,9b-dihydrooxireno[2,3-a]acridine
• CAS: 159700-54-6
• 化学式: C₁₃H₉NO
• 分子量: 195.221
• InChiKey: FJRTWUDZFLUIHA-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(1R,2S)-1,2-epoxy-1,2-dihydroacridine 在 氢氧化钾 作用下， 以 叔丁醇 为溶剂， 生成 (+)-(1S,2S)-trans-1,2-dihydroacridine-1,2-diol 、 (-)-(1R,2R)-trans-1,2-dihydroacridine-1,2-diol
  参考文献：
  名称：

  Chemical synthesis of the (1R,2S) and (1S,2R) arene oxide metabolites of acridine

  摘要：

  Enantiopure samples of (+)-(1R,2S) and (-)-(1S,2R)-1,2-epoxy-1,2-dihydroacridine 4 have been obtained from the corresponding trans-2-bromo-1,2,3,4-tetrahydroacridin-1-ol MTPA esters 7a and b. Absolute configurations were deduced by stereochemical correlation to (+)-(1R,2R)-trans-2-bromo-1-(2-methoxy-2-phenyl-2-trifluoroacetoxy)-1,2,3,4-acridine 7a which was unequivocally assigned by X-ray crystal structure analysis. (-)-(1R,2R)-trans-1,2-Dihydroacridine-1,2-diol 2 was obtained by alkaline hydrolysis of (+)-(1R,2S) -acridine 1,2-oxide 4.

  DOI：

  10.1039/p19940002711
• 作为产物：
  描述：

  吖啶 在 biphenyl dioxygenase from Sphingomonas yanoikuyae B₈/36 、 氧气 、 sodium methylate 作用下， 生成 (+)-(1R,2S)-1,2-epoxy-1,2-dihydroacridine
  参考文献：
  名称：

  Multiple site dioxygenase-catalysed cis-dihydroxylation of polycyclic azaarenes to yield a new class of bis-cis-diol metabolites

  摘要：

  三环氮杂烯类新的单顺式二氢二醇细菌代谢物的稳定性增强，促进了二氧化酶催化的相应双顺式二氢二醇（顺式四醇）的形成和分离，以及衍生的氧化炔哺乳动物代谢物的三步化学酶法途径。

  DOI：

  10.1039/a902427a

文献信息

• Multiple site dioxygenase-catalysed cis-dihydroxylation of polycyclic azaarenes to yield a new class of bis-cis-diol metabolites
  作者：Derek R. Boyd、Narain D. Sharma、Jonathan G. Carroll、Christopher C. R. Allen、David A. Clarke、David T. Gibson

  DOI：10.1039/a902427a

  日期：——

  The enhanced stability of new mono-cis-dihydrodiol bacterial metabolites of tricyclic azaarenes has facilitated the dioxygenase-catalysed formation and isolation of the corresponding bis-cis-dihydrodiols (cis-tetraols) and a three step chemoenzymatic route to the derived arene oxide mammalian metabolites.

  三环氮杂烯类新的单顺式二氢二醇细菌代谢物的稳定性增强，促进了二氧化酶催化的相应双顺式二氢二醇（顺式四醇）的形成和分离，以及衍生的氧化炔哺乳动物代谢物的三步化学酶法途径。
• Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids
  作者：Derek R. Boyd、Narain D. Sharma、Jonathan G. Carroll、Pui L. Loke、Colin R. O'Dowd、Christopher C. R. Allen

  DOI：10.1039/c3ra42026d

  日期：——

  Biotransformation of acridine, dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings. cis-Dihydroxylation of the furan ring in dictamnine and 4-chlorofuro[2,3-b]quinoline, followed by ring opening and reduction, yielded two exocyclic

  yan啶鞘氨醇单胞菌B8 / 36的全细胞对a啶，三氢嘧啶和4-氯呋喃并[2,3- b ]喹诺酮进行生物转化，由联苯双加氧酶催化的碳环的二羟基化反应产生了五个对映体纯的环状顺式-二氢二醇。胺和4-氯呋喃并[2,3- b ]喹啉中呋喃环的顺式-二羟基化，然后开环还原，生成了两种环外二醇。代谢物的结构和绝对构型已通过光谱学和立体化学相关方法确定。从相应的顺式合成了a啶和三氢萘胺的对映体纯的氧化芳烃代谢物-二氢二醇。非手性呋喃喹啉生物碱强健碱，γ-甘氨酸，单倍体，异单倍体3,3'-二甲基烯丙基醚和蝶呤已从顺苯二胺的顺式-二氢二醇，儿茶酚或氧化芳烃代谢物获得。
• Chemical synthesis of the (1R,2S) and (1S,2R) arene oxide metabolites of acridine
  作者：Derek R. Boyd、Michael R. J. Dorrity、Lynne Hamilton、John F. Malone、Allison Smith

  DOI：10.1039/p19940002711

  日期：——

  Enantiopure samples of (+)-(1R,2S) and (-)-(1S,2R)-1,2-epoxy-1,2-dihydroacridine 4 have been obtained from the corresponding trans-2-bromo-1,2,3,4-tetrahydroacridin-1-ol MTPA esters 7a and b. Absolute configurations were deduced by stereochemical correlation to (+)-(1R,2R)-trans-2-bromo-1-(2-methoxy-2-phenyl-2-trifluoroacetoxy)-1,2,3,4-acridine 7a which was unequivocally assigned by X-ray crystal structure analysis. (-)-(1R,2R)-trans-1,2-Dihydroacridine-1,2-diol 2 was obtained by alkaline hydrolysis of (+)-(1R,2S) -acridine 1,2-oxide 4.