trans-10-azido-9,10-dihydrophenanthren-9-ol | 53581-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: trans-10-azido-9,10-dihydrophenanthren-9-ol
• 英文别名: (9S,10S)-10-azido-9,10-dihydrophenanthren-9-ol
• CAS: 53581-32-1
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: BBWLKNHCRZAQMC-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-10-azido-9,10-dihydrophenanthren-9-ol 在 三甲氧基磷 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 菲
  参考文献：
  名称：

  Weitzberg, Moshe; Avnir, David; Aizenshtat, Zeev, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1019 - 1022

  摘要：

  DOI：
• 作为产物：
  描述：

  9,10-环氧-9,10-二氢菲 在 sodium azide 作用下， 以 乙醇 为溶剂， 生成 trans-10-azido-9,10-dihydrophenanthren-9-ol
  参考文献：
  名称：

  Nucleophilic displacement on the arene oxides of phenanthrene

  摘要：

  DOI：

  10.1021/ja00426a049

文献信息

• Zum Mechanismus der Aziridinsynthese aus 2-Azidoalkoholen und Triphenylphosphin
  作者：Peter Pöchlauer、Ernst Peter Müller、Paul Peringer

  DOI：10.1002/hlca.19840670510

  日期：1984.8.8

  On the Mechanism of the Aziridine Synthesis from 2-Azido-alcohols and Triphenylphosphine

  从2-叠氮基醇和三苯基膦合成氮丙啶的机理研究
• Reduction and Hydrocyanation of Aziridines with C−C Bond Cleavage
  作者：Yuki Kawamoto、Tomoyuki Yoshimura、Jun‐ichi Matsuo

  DOI：10.1002/ejoc.202400613

  日期：2024.10.14

  Unusual C−C bond cleavage of 2,3-diaryl aziridines took place to afford secondary amines by formal dihydrogenation and hydrocyanation. Formal dehydrogenation was performed by electrocyclic ring opening of N-Li or N-Na aziridines to azaallyl anions followed by reduction with NaBH4. Formal hydrocyanation was realized by treating azaallyl anions with Me3SiCN.

  2,3-二芳基氮丙啶的不寻常 C-C 键裂解通过正式的二氢化和氢氰化得到仲胺。通过将 N-Li 或 N-Na 氮杂环啶电循环开环化为氮杂烯丙基阴离子，然后用 NaBH4 还原来进行正式脱氢。通过用 Me3SiCN 处理氮杂烯丙基阴离子实现正式氢氰化。
• Synthesis and Assignment of Absolute Configuration to the N6-Deoxyadenosine Adducts Resulting from Cis and Trans Ring-Opening of Phenanthrene 9,10-Oxide
  作者：Mahesh K. Lakshman、Wei Xiao、Jane M. Sayer、Albert M. Cheh、Donald M. Jerina

  DOI：10.1021/jo00086a027

  日期：1994.4

  Reaction of calf thymus DNA with phenanthrene 9,10-oxide in vitro results in alkylation of the exocyclic amino groups of the purine bases. Adducts result from both cis and trans opening of the epoxide. In the present study, structures of the N-6-deoxyadenosine adducts have been unequivocally assigned by synthesis from optically pure cis- and trans-9-amino-10-hydroxy-9,10-dihydrophethrene. Resolution of trans-9-azido-10-hydroxy-9,10-dihydrophenanthrene as its acetate was achieved on a chiral. HPLC column. The early-eluting (-)-enantiomer was assigned (9R,10R)-absolute configuration based on a characteristic negative CD band at 232 nm due to the helicity of its biphenyl chromophore, in combination with a H-1 NMR coupling constant that indicated pseudodiaxial orientation of the substituents at C-9 and C-10. Aminolysis of the ester followed by reduction of the azido group provided the desired, optically active trans (9R,10R) amino alcohol. As a starting material for synthesis of the cis amino alcohol, trans-9-bromo-10-acetoxy-9,10-dihydrophe was resolved by chiral HPLC. As above, the early-eluting (-)-enantiomer was assigned (9R,10R)absolute configuration based on a characteristic negative CD band at 234 nm. Displacement of bromine with inversion of configuration by azide, aminolysis of the ester, and reduction provided optically pure cis-(9S,10R)-9-amino-10-hydroxy-9,10-dihydrophenanthrene. Coupling of the optically active amino alcohols with 6-fluoro-9-(2-deoxy-beta-D-erythro-pentofuranosyl) purine (the 6-fluoro analog of dA) yielded the corresponding N-6-deoxyadenosine adducts. Comparison of CD spectra and HPLC retention times of the synthetic adducts with those of the adducts obtained from calf thymus DNA make it possible to assign unambiguously the structures of the DNA adducts.
• Shtelzer, Sarah; Weitzberg, Moshe; Jeries, Juliette, Journal of Heterocyclic Chemistry, 1984, vol. 21, # 1, p. 1 - 3
  作者：Shtelzer, Sarah、Weitzberg, Moshe、Jeries, Juliette、Sheradsky, Tuvia、Aizenshtat, Zeev、Blum, Jochanan

  DOI：——

  日期：——
• Synthesis and antimalarial evaluation of 9,10-dihydrophenanthrene amino alcohols
  作者：Adrienne S. Dey、John L. Neumeyer

  DOI：10.1021/jm00256a015

  日期：1974.10