(+)-(3S,4R)-3,4-dihydroxy-3,4-dihydrochrysene | 193553-19-4

• 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: (+)-(3S,4R)-3,4-dihydroxy-3,4-dihydrochrysene
• 英文别名: (3S,4R)-3,4-dihydrochrysene-3,4-diol
• CAS: 193553-19-4
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: XOKPMCWSKPASGO-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4R)-3,4-dihydroxy-3,4-dihydrochrysene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (-)-(3S,4R)-cis-3,4-dihydroxy-1,2,3,4-tetrahydrochrysene
  参考文献：
  名称：

  Boyd, Derek R.; Sharma, Narain D.; Agarwal, Rajiv, Journal of the Chemical Society. Perkin transactions I, 1997, # 11, p. 1715 - 1723

  摘要：

  DOI：
• 作为产物：
  描述：

  屈 在 potassium phosphate buffer 、 丙酮酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (+)-(3S,4R)-3,4-dihydroxy-3,4-dihydrochrysene
  参考文献：
  名称：

  Boyd, Derek R.; Sharma, Narain D.; Agarwal, Rajiv, Journal of the Chemical Society. Perkin transactions I, 1997, # 11, p. 1715 - 1723

  摘要：

  DOI：

文献信息

• Enantiopurity and absolute configuration determination of arene<i>cis</i>-dihydrodiol metabolites and derivatives using chiral boronic acids
  作者：Derek R. Boyd、Narain D. Sharma、Peter A. Goodrich、John F. Malone、Gareth McConville、John S. Harrison、Paul J. Stevenson、Christopher C.R. Allen

  DOI：10.1002/chir.22764

  日期：2018.1

  cis‐dihydrodiol, cyclohex‐2‐en‐1‐one cis‐diol, heteroarene cis/trans‐2,3‐diol, and catechol metabolites in estimating their ee values, and 2) new chiral phenylboronic acids, 2‐[1‐methoxy‐2,2‐dimethylpropyl]phenyl boronic acid (MDPBA) and 2‐[1‐methoxy‐1‐phenylmethyl]phenyl boronic acid (MPPBA) and their advantages over MEPBA, as reagents for stereochemical analysis of arene and alkene cis‐diol metabolites, are presented

  的用于确定对映体过量（方法相对优点EE）值和手性芳烃绝对构型和烯烃的顺式-1,2-二醇的代谢物，包括硼酸酯的形成，使用外消旋或对映纯的（+）和（ - ） - 2-讨论了（1-甲氧基乙基）苯基硼酸（MEPBA）。的进一步的应用：1）衍生MEPBA手性的单-和多环芳烃的硼酸盐顺式-dihydrodiol，环己-2-烯-1-酮的顺式-二醇，杂芳烃顺/反式-2,3-二醇，和儿茶酚代谢物在估计他们的ee值； 2）新的手性苯基硼酸，2- [1- [1-甲氧基-2,2-二甲基丙基]苯基硼酸（MDPBA）和2- [1-甲氧基-1-苯基甲基]苯基硼酸（MPPBA）及其优势介绍了在MEPBA上作为芳烃和烯烃顺式-二醇代谢物的立体化学分析试剂。
• <i>bis-cis</i>-Dihydrodiols:  A New Class of Metabolites Resulting from Biphenyl Dioxygenase-Catalyzed Sequential Asymmetric <i>cis</i>-Dihydroxylation of Polycyclic Arenes and Heteroarenes
  作者：Derek R. Boyd、Narain D. Sharma、Francis Hempenstall、Martina A. Kennedy、John. F. Malone、Christopher C. R. Allen、Sol M. Resnick、David T. Gibson

  DOI：10.1021/jo982517n

  日期：1999.5.1

  The biphenyl dioxygenase-catalyzed asymmetric mono-cis-dihydroxylation of the tetracyclic arenes chrysene 1A, benzo[c]phenanthridine 1B, and benzo[b]naphtho[2,1-d]thiophene 1C, has been observed to occur exclusively at the bay or pseudo-bay region using the bacterium Sphingomonas yanoikuyae B8/36. The mono-cis-dihydrodiol derivatives 2A and 2C, obtained from chrysene 1A by oxidation at the 3,4-bond (2A) and benzo[b]naphtho[2,1-d]thiophene 1C by oxidation at the 1,2-bond (2C), respectively, have been observed to undergo a further dioxygenase-catalyzed asymmetric cis-dihydroxylation at a second bay or pseudo-bay region bond to yield the corresponding bis-cis-dihydrodiols (cis-tetraols) 4A and 4C, the first members of a new class of microbial metabolites in the polycyclic arene series. The enantiopurities and absolute configurations of the new mono-cis-dihydrodiols 2B, 2C, and 3B were determined by H-1 NMR analyses of the corresponding (R)- and (S)-2-(1-methoxyethyl)benzeneboronate (MPBA) ester derivatives. The structure and absolute configurations of the bis-cis-dihydrodiols 4A and 4C were unambiguously determined by spectral analyses, stereochemical correlations, and, for the metabolite 4C, X-ray crystallographic analysis of the bis-acetonide derivative 7C. These results illustrate the marked preference of biphenyl dioxygenase for the cis-di- and tetra-hydroxylations of polycyclic arenes, at the more hindered bay or pseudo-bay regions, by exclusive addition from the same (si:si) face, to yield single enantiomers containing two and four chiral centers.
• Boyd, Derek R.; Sharma, Narain D.; Agarwal, Rajiv, Journal of the Chemical Society. Perkin transactions I, 1997, # 11, p. 1715 - 1723
  作者：Boyd, Derek R.、Sharma, Narain D.、Agarwal, Rajiv、Resnick, Sol M.、Schocken, Mark J.、Gibson, David T.、Sayer, Jane M.、Yagi, Haruhiko、Jerina, Donald M.

  DOI：——

  日期：——