ethyl 3-chrysenecarboxylate | 96403-22-4

• 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: ethyl 3-chrysenecarboxylate
• 英文别名: ethyl chrysene-3-carboxylate
• CAS: 96403-22-4
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: NGOOILKVBOXCLE-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  503.5±19.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3-chrysenecarboxylate 在 sodium tetrahydroborate 、 锂硼氢 、 barium permanganate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 2-((3-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol
  参考文献：
  名称：

  2-[(Arylmethyl)amino]-2-methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding

  摘要：

  The effects of variation of aromatic ring size, shape, and side-chain position on antitumor activity and DNA binding in a series of carbocyclic 2-[(arylmethyl)amino]-2-methyl-1,3-propanediols (AMAPs) were examined. In general, the interaction of AMAPs with DNA increases as the intercalating ring system grows in area, with three distinct binding levels evident. Isomers from a specific ring system appear to bind DNA similarly. DNA binding is not the sole criterion for antitumor activity for the AMAPs studied; the magnitude of the DELTA-T(m) does not correlate with the antitumor activity observed. Significant in vivo P388 activity was seen for AMAP congeners from several tetracyclic ring systems. However, isomers from each of the specific ring systems produced a wide range of in vivo P388 activity. Thus, AMAP antitumor activity is not a function of the ring system per se, but rather appears to be related to the shape of the specific molecule. Three AMAP congeners (crisnatol (770U82, 773U82, and 502U83) are currently in clinical trials.

  DOI：

  10.1021/jm00111a010
• 作为产物：
  描述：

  屈 在 sodium hydroxide 、 sodium hypochlorite 、 三氯化铝 、 硫酸 作用下， 以 水 、 硝基苯 为溶剂， 反应 96.0h， 生成 ethyl 3-chrysenecarboxylate
  参考文献：
  名称：

  2-[(Arylmethyl)amino]-2-methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding

  摘要：

  The effects of variation of aromatic ring size, shape, and side-chain position on antitumor activity and DNA binding in a series of carbocyclic 2-[(arylmethyl)amino]-2-methyl-1,3-propanediols (AMAPs) were examined. In general, the interaction of AMAPs with DNA increases as the intercalating ring system grows in area, with three distinct binding levels evident. Isomers from a specific ring system appear to bind DNA similarly. DNA binding is not the sole criterion for antitumor activity for the AMAPs studied; the magnitude of the DELTA-T(m) does not correlate with the antitumor activity observed. Significant in vivo P388 activity was seen for AMAP congeners from several tetracyclic ring systems. However, isomers from each of the specific ring systems produced a wide range of in vivo P388 activity. Thus, AMAP antitumor activity is not a function of the ring system per se, but rather appears to be related to the shape of the specific molecule. Three AMAP congeners (crisnatol (770U82, 773U82, and 502U83) are currently in clinical trials.

  DOI：

  10.1021/jm00111a010

文献信息

• Crysene compound
  申请人：Burroughs Wellcome Co.

  公开号：US04719048A1

  公开（公告）日：1988-01-12

  The present invention relates to compounds of formula (I) ArCH.sub.2 R.sup.1 (I) or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a chrysene or substituted chrysene ring system; R.sup.1 contains not more than eight carbon atoms and is a group ##STR1## wherein m is 0 or 1; R.sup.5 is hydrogen; R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy; R.sup.8 and R.sup.9 are the ame or different and each is hydrogen or C.sub.1-3 alkyl; ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl; R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl; R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.

  本发明涉及通式(I)ArCH₂R¹(I)的化合物或其单甲基或单乙基醚(通式(I)的化合物包括这些醚，其总共含有不超过30个碳原子); 醚、酯及其酸加成盐; 其中Ar是晕苯或取代晕苯环系; R¹含有不超过八个碳原子，是如下所示的基团##STR1##其中m是0或1; R⁵是氢; R⁶和R⁷相同或不同，各自是氢或C₁-₃烷基，可选择性地被羟基取代; R⁸和R⁹相同或不同，各自是氢或C₁-₃烷基; ##STR2##是一个五元或六元饱和碳环; R¹⁰是氢、甲基或羟甲基; R¹¹、R¹²和R¹³相同或不同，各自是氢或甲基; R¹⁴是氢、甲基、羟基或羟甲基。
• Crysene derivatives
  申请人：Burroughs Wellcome Co.

  公开号：US04719046A1

  公开（公告）日：1988-01-12

  The present invention relates to compounds of formula (I) ArCH.sub.2 R.sup.1 (I) or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a chrysene or substituted chrysene ring system; R.sup.1 contains not more than eight carbon atoms and is a group ##STR1## wherein m is 0 or 1; R.sup.5 is hydrogen; R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy; R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl, ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl; R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl; R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.

  本发明涉及式(I)ArCH.sub.2 R.sup.1(I)的化合物或其单甲基或单乙基醚(式(I)化合物包括这些醚，可能总共含有不超过30个碳原子);其醚、酯;其酸加成盐;其中Ar是晕苯或取代晕苯环系;R.sup.1包含不超过八个碳原子，并且是如下所示的基团##STR1##其中m是0或1;R.sup.5是氢;R.sup.6和R.sup.7相同或不同，各自为氢或C.sub.1-3烷基，任选被羟基取代;R.sup.8和R.sup.9相同或不同，各自为氢或C.sub.1-3烷基，##STR2##是五元或六元饱和碳环;R.sup.10是氢、甲基或羟甲基;R.sup.11、R.sup.12和R.sup.13相同或不同，各自为氢或甲基;R.sup.14是氢、甲基、羟基或羟甲基。
• Chrysene compound
  申请人：Burroughs Wellcome Co.

  公开号：US04810727A1

  公开（公告）日：1989-03-07

  The present invention relates to compounds of formula (I) ArCH.sub.2 R.sup.1 (I) or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a chrysene or substituted chrysene ring system; R.sup.1 contains not more than eight carbon atoms and is a group ##STR1## wherein m is 0 or 1; R.sup.5 is hydrogen; R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy; R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl; --C--C-- is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl; R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl; R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.

  本发明涉及式(I) ArCH.sub.2R.sup.1(I)化合物或其单甲基或单乙基醚（式(I)化合物包括这些醚，总碳原子数不超过30）；醚，酯；其酸加成盐；其中Ar是蒽或取代蒽环系统；R.sup.1不超过八个碳原子，是一个基团##STR1##其中m为0或1；R.sup.5是氢；R.sup.6和R.sup.7相同或不同，每个是氢或C.sub.1-3烷基，可选地被羟基取代；R.sup.8和R.sup.9相同或不同，每个是氢或C.sub.1-3烷基；--C--C--是一个五元或六元饱和碳环；R.sup.10是氢，甲基或羟甲基；R.sup.11，R.sup.12和R.sup.13相同或不同，每个是氢或甲基；R.sup.14是氢，甲基，羟基或羟甲基。
• Chrysene derivatives
  申请人：Burroughs Wellcome Co.

  公开号：US04829090A1

  公开（公告）日：1989-05-09

  The present invention relates to compounds of formula (I) ArCH.sub.2 R.sup.1 (I) or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a chrysene or substituted chrysene ring system; R.sup.1 contains not more than eight carbon atoms and is a group ##STR1## wherein m is 0 or 1; R.sup.5 is hydrogen; R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy; R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl; ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl; R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl; R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.

  本发明涉及式(I)的化合物 ArCH.sub.2 R.sup.1(I)或其甲基或乙基单醚（包括这些醚的式(I)化合物总共不超过30个碳原子）；它们的醚、酯；它们的酸加成盐；其中Ar是蒽或取代蒽环系统；R.sup.1不含超过八个碳原子，是一个基团##STR1##其中m为0或1；R.sup.5为氢；R.sup.6和R.sup.7相同或不同，每个都是氢或C.sub.1-3烷基，可选地被羟基取代；R.sup.8和R.sup.9相同或不同，每个都是氢或C.sub.1-3烷基；##STR2##是一个五元或六元饱和碳环；R.sup.10为氢、甲基或羟甲基；R.sup.11、R.sup.12和R.sup.13相同或不同，每个都是氢或甲基；R.sup.14为氢、甲基、羟基或羟甲基。
• Cascade Synthesis of Phenanthrenes under Photoirradiation
  作者：Yongkang Li、Dan E. Wise、Joshua K. Mitchell、Marvin Parasram

  DOI：10.1021/acs.joc.2c02202

  日期：2023.1.6

  We report a photoinduced phenanthrene synthesis from aryl iodides and styrenes through an arylation/cyclization cascade. Compared to prior methods, this approach obviates the need for hazardous reagents and provides access to unsymmetrical phenanthrenes with good functional group tolerance. Mechanistic studies revealed that photoexcitation of aryl iodides leads to homolytic C–I bond cleavage. Arylation

  我们通过芳基化/环化级联报告了芳基碘化物和苯乙烯的光诱导菲合成。与以前的方法相比，这种方法避免了对危险试剂的需要，并提供了获得具有良好官能团耐受性的不对称菲的途径。机理研究表明，芳基碘化物的光激发会导致均裂的 C-I 键断裂。苯乙烯与形成的芳基自由基物种的芳基化提供二苯乙烯衍生物，其经历由原位产生的碘促进的光诱导环化以产生菲产物。