1a,2,3,9c-四氢-菲并(3,4-b)环氧乙烯 | 66997-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 1a,2,3,9c-四氢-菲并(3,4-b)环氧乙烯
• 英文名称: 1,2,3,4-tetrahydrophenanthrene 3,4-oxide
• 英文别名: 1,2,3,4-tetrahydrophenanthrene-3,4-oxide；tetrahydrophenanthrene-3,4-epoxide；3,4-Epoxy-1,2,3,4-tetrahydrophenanthrene；14-oxatetracyclo[8.5.0.02,7.013,15]pentadeca-1(10),2,4,6,8-pentaene
• CAS: 66997-69-1
• 化学式: C₁₄H₁₂O
• 分子量: 196.249
• InChiKey: OEQLVOBTUGIXQP-UHFFFAOYSA-N

物化性质

• 沸点：
  293.14°C (rough estimate)
• 密度：
  1.0304 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1a,2,3,9c-四氢-菲并(3,4-b)环氧乙烯 在 N,N-二甲基硫代甲酰胺 、 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,2-二氢菲
  参考文献：
  名称：

  Synthesis and Characterization of Thermodynamically Unstable Polycyclic Aromatic Hydrocarbon Episulfides and Episulfoxides

  摘要：

  DOI：

  10.1021/jo000086e
• 作为产物：
  描述：

  3-bromo-1,2,3,4-tetrahydro-4-hydroxyphenanthrene 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以83%的产率得到1a,2,3,9c-四氢-菲并(3,4-b)环氧乙烯
  参考文献：
  名称：

  Synthesis and Characterization of Thermodynamically Unstable Polycyclic Aromatic Hydrocarbon Episulfides and Episulfoxides

  摘要：

  DOI：

  10.1021/jo000086e

文献信息

• Synthesis and site-specific incorporation of a bay-region cis ring-opened tetrahydro epoxide-deoxyadenosine adduct into a DNA oligomer
  作者：Mahesh K. Lakshman、Jane M. Sayer、Donald M. Jerina

  DOI：10.1021/jo00038a037

  日期：1992.6

  Chemical synthesis of the 1,2,3,4-tetrahydrophenanthrene 3,4-epoxide adducts resulting from benzylic, cis ring-opening of the epoxide by the exocyclic amino group of 2'-deoxyadenosine (dA) is described. The approach taken consists of coupling (+/-)-cis-3-hydroxy-4-amino-1,2,3,4-tetrahydrophenanthrene with a 6-fluoro analogue of dA in which the furanose hydroxyl groups are protected. The required amino alcohol was obtained by reaction of 1,2-dihydrophenanthrene with osmium tetraoxide to form the cis 3,4-diol, conversion to the trans chlorohydrin benzoate via its orthobenzoate, displacement of the benzylic chloride by azide, hydrolysis to the cis azido alcohol, and reduction to the racemic cis amino alcohol. Coupling of the amino alcohol with the 3',5'-bis-O-(tert-butyldimethylsilyl) derivative of 6-fluoro-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine results in a pair of diastereomers that are readily separated by HPLC on silica gel. Replacement of the previously used pyridine by 2,6-lutidine significantly improved the yield for the coupling step. Both adducts were acetylated on the hydroxyl group of the hydrocarbon and then desilylated on the sugar. Absolute configurations were assigned to the adducts on the basis of the shapes of their CD spectra. The 3S,4R diastereomer (derived from the more polar, late-eluting adduct) was blocked at the 5'-sugar hydroxyl group with the 4,4'-dimethoxytrityl group and allowed to react with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite to produce the desired activated nucleoside. Incorporation into the deoxynucleotide TpGpA*pGpT as the central base proceeded in good yield with minor modifications to the standard DNA synthesizer protocol.
• Laksman, Mahesh K.; Sayer, Jane M.; Jerina, Donald M., Journal of the American Chemical Society, 1991, vol. 113, # 17, p. 6589 - 6594
  作者：Laksman, Mahesh K.、Sayer, Jane M.、Jerina, Donald M.

  DOI：——

  日期：——
• Synthesis and Characterization of Thermodynamically Unstable Polycyclic Aromatic Hydrocarbon Episulfides and Episulfoxides
  作者：Uri Zoller、Fa-Pu Chen

  DOI：10.1021/jo000086e

  日期：2000.11.1