3,4-Phenanthrenediol, 1,2,3,4-tetrahydro-, trans- | 60967-96-6

• 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: 3,4-Phenanthrenediol, 1,2,3,4-tetrahydro-, trans-
• 英文别名: 3,4-Phenanthrenediol, 1,2,3,4-tetrahydro-, (3R-cis)-；(+)-trans-3,4-dihydroxy-1,2,3,4-tetrahydrophenanthrene；(+/-)-cis-3,4-dihydroxy-1,2,3,4-tetrahydrophenanthrene；(+/-)-cis-1,2,3,4-tetrahydro-phenanthrene-3,4-diol；(+/-)-cis-1,2,3,4-Tetrahydro-phenanthren-3,4-diol；(+)-(3R,4S)-cis-3,4-dihydroxy-1,2,3,4-tetrahydrophenanthrene；1,2,3,4-Tetrahydrophenanthren-cis-3,4-diol
• CAS: 60967-96-6；64069-90-5；78549-57-2；89772-82-7；89772-84-9；141193-98-8；147200-21-3
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: MJYGNFMCMVMALV-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,4-Phenanthrenediol, 1,2,3,4-tetrahydro-, trans- 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以63%的产率得到3,4-菲醌
  参考文献：
  名称：

  由环酮合成多环芳烃的非k区醌

  摘要：

  多环芳烃的非K区醌是由环酮通过四氢二醇与2,3-二氯-5,6-二氰基-1,4-苯醌的脱氢反应从四环酮中分四个步骤制得的。

  DOI：

  10.1016/s0040-4039(00)86775-1
• 作为产物：
  描述：

  1,2-二氢菲 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到3,4-Phenanthrenediol, 1,2,3,4-tetrahydro-, trans-
  参考文献：
  名称：

  菲，联苯，苯并[ a，c ]蒽和苯并[ a，h ]蒽的氧化芳烃代谢产物的合成和异构化

  摘要：

  由对映纯的二溴MTPA前体9A RRS *合成的Dibenz [ a，h ]蒽3,4-氧化物5A RS被发现已完全消旋，并伴随有苯并[5,6]蒽[1,2- b ]奥沙平 11A。菲3,4-氧化物5B RS，从对映纯细菌中获得代谢物 观察到，通过涉及氯醇酯16B的改进的合成方法，顺式-3,4-二羟基-3,4-二氢菲12B在环境温度下自发消旋。Dibenz [ a，h ]蒽3,4-氧化物5A RS / 5A SR，菲3,4-氧化物5B RS / 5B SR，联苯1,2-氧化物5C RS / 5C SR和dibenz [ a，c ]蒽1,2-氧化物5D RS / 5D SR通过新方法从相应的外消旋顺式-四氢二醇前体14A - 14D获得的，没有任何证据表明形成了苯并[5,6]蒽[1,2- b ]奥沙平 11A，萘[1,2- b ]奥西平 11B，菲咯[10,9- b ]奥沙平 分别为11C或苯并[3

  DOI：

  10.1039/b009712h

文献信息

• Regio and stereocontrolled synthesis of aryl cis aminoalcohols from cis glycols
  作者：Mahesh K. Lakshman、Barbara Zajc

  DOI：10.1016/0040-4039(96)00334-6

  日期：1996.4

  Reaction of aryl substituted cis diols with α-acetoxyisobutyryl chloride results in the formation of trans vicinal chlorohydrin acetates where the halide is benzylic. Displacement of chloride with azide ion, deprotection of the ester and reduction of the azide furnishes the requisite cis aminoalcohols. This facile four-step procedure results in the exclusive replacement of a benzylic hydroxyl with

  芳基取代的顺式二醇与α-乙酰氧基异丁酰氯的反应导致反式邻氯氯代乙酸酯的形成，其中卤化物是苄基的。用叠氮化物离子置换氯离子，使酯脱保护并还原叠氮化物，提供了必需的顺式氨基醇。这种简便的四步操作程序可将苄基羟基专门替换为氨基，并保留了立体化学结构。这组转化通常适用于多种顺式二醇，并且总收率非常好。
• Dannenberg; Dannenberg-v. Dresler, Zeitschrift fur Naturforschung, 1952, vol. 7b, p. 265,267
  作者：Dannenberg、Dannenberg-v. Dresler

  DOI：——

  日期：——
• Balani, Suresh K.; Boyd, Derek R.; Cassidy, E. Sally, Journal of the Chemical Society. Perkin transactions I, 1983, # 11, p. 2751 - 2756
  作者：Balani, Suresh K.、Boyd, Derek R.、Cassidy, E. Sally、Devine, Gregory I.、Malone, John F.、et al.

  DOI：——

  日期：——
• 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.
• Synthesis and isomerization of arene oxide metabolites of phenanthrene, triphenylene, dibenz[a,c]anthracene and dibenz[a,h]anthracene
  作者：Suresh K. Balani、I. N. Brannigan、Derek R. Boyd、Narain D. Sharma、Francis Hempenstall、Allison Smith

  DOI：10.1039/b009712h

  日期：——

  phenanthro[10,9-b]oxepine 11C, or benz[3,4]anthra[1,2-b]oxepine 11D isomers respectively. The total racemization of arene oxide 5ARS and formation of oxepine 11A from the bromoMTPA precursor 8ARRS* are in accord with earlier PMO predictions based on resonance energy considerations. Photoisomerization of arene oxides 5ARS/5ASR, 5CRS/5CSR, and 5DRS/5DSR was found to yield the corresponding oxepines 11A, 11C,

  由对映纯的二溴MTPA前体9A RRS *合成的Dibenz [ a，h ]蒽3,4-氧化物5A RS被发现已完全消旋，并伴随有苯并[5,6]蒽[1,2- b ]奥沙平 11A。菲3,4-氧化物5B RS，从对映纯细菌中获得代谢物 观察到，通过涉及氯醇酯16B的改进的合成方法，顺式-3,4-二羟基-3,4-二氢菲12B在环境温度下自发消旋。Dibenz [ a，h ]蒽3,4-氧化物5A RS / 5A SR，菲3,4-氧化物5B RS / 5B SR，联苯1,2-氧化物5C RS / 5C SR和dibenz [ a，c ]蒽1,2-氧化物5D RS / 5D SR通过新方法从相应的外消旋顺式-四氢二醇前体14A - 14D获得的，没有任何证据表明形成了苯并[5,6]蒽[1,2- b ]奥沙平 11A，萘[1,2- b ]奥西平 11B，菲咯[10,9- b ]奥沙平 分别为11C或苯并[3