3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one | 792-07-4

• 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: 3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one
• 英文别名: 15,16-dihydro-3-methoxycyclopentaphenanthren-17-one；3-Methoxy-15,16-dihydro-cyclopentaphenanthren-17-on；3-Methoxy-15,16-dihydro-cyclopenta[a]phenanthren-17-on；17H-Cyclopenta(a)phenanthren-17-one, 15,16-dihydro-3-methoxy-；3-methoxy-15,16-dihydrocyclopenta[a]phenanthren-17-one
• CAS: 792-07-4
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: NENWDIKRKLJSOX-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  479.7±14.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

SDS

反应信息

• 作为反应物：
  描述：

  3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one 在 platinum(IV) oxide 氢气 作用下， 生成 16,17-二氢-3-甲氧基-17-甲基-15H-环戊二烯并(a)菲
  参考文献：
  名称：

  潜在致癌的环戊并[ a ]菲（1,2-环戊烯并菲）。第二部分 环D中含有进一步不饱和键的衍生物

  摘要：

  通过格氏反应从相应的15,16-二氢-17-酮制备了取代的17-甲基-15 H-环戊[ a ]菲，并将其还原为Diels烃的类似物。通过Witting反应获得15，16-二氢-17-亚甲基衍生物（未取代）。消除从17甲苯p在170 -sulphonyloxy化合物°得到Δ 15 - 17 ħ -化合物（A），但在100℃的Δ 16 - 15 ħ形成异构体。（A）与丙酮和芳基醛的碱催化缩合产生17-取代的亚甲基衍生物。列出了这些化合物中连接在环D上的质子的化学位移。

  DOI：

  10.1039/j39660000963
• 作为产物：
  描述：

  16,17-dihydro-3-methoxy-15H-cyclopentaphenanthren-17-one 在 palladium on activated charcoal palladium on activated charcoal 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 溶剂黄146 为溶剂， 生成 3-methoxy-16,17-dihydro-15H-cyclopenta-phenanthren-17-one
  参考文献：
  名称：

  环戊达[a]菲及其致癌衍生物的新合成

  摘要：

  描述了环戊[a]菲及其致癌的11-甲基和17-酮衍生物的新颖合成。

  DOI：

  10.1016/0040-4039(88)85123-2

文献信息

• Potentially carcinogenic cyclopenta[a]phenanthrenes (1,2-cyclopentenophenanthrenes). Part I. A new synthesis of 15,16-dihydro-17-oxocyclopenta[a]phenanthrene and the phenanthrene analogue of 18-norœstrone methyl ether
  作者：M. M. Coombs

  DOI：10.1039/j39660000955

  日期：——

  15,16-Dihydro-17-oxocyclopenta[a]phenanthrene and its 3-methoxy, 11- and 12-methyl, and 11,12-dimethyl, derivatives have been synthesised by aromatisation of the 3-unsubstituted and 3-methoxy-11,17-diketones in which rings C and D are both saturated; the mechanism of the aromatisation is discussed.

  通过将3-未取代的和3-甲氧基-11芳构化，合成了15,16-二氢-17-氧代环戊[ a ]菲及其3-甲氧基，11-和12-甲基以及11,12-二甲基衍生物。C，D环均饱和的，17-二酮；讨论了芳构化的机理。
• New synthetic approaches to cyclopenta[a]phenanthrenes and their carcinogenic derivatives
  作者：Hongmee Lee、Ronald G. Harvey

  DOI：10.1021/jo00253a017

  日期：1988.9
• Synthesis of the putative active metabolites of the cyclopenta[a]phenanthrenes. Synthesis of the trans-3,4-dihydro-3,4-diol and syn-3,4-diol 1,2-epoxide derivatives of the mutagen 15,16-dihydrocyclopenta[a]phenanthren-17-one
  作者：Stephen A. Woski、Masato Koreeda

  DOI：10.1021/jo00047a030

  日期：1992.10

  The first synthesis of the trans-dihydro diol and syn-diol epoxide derivatives of a biologically active cyclopenta[a]phenanthrene is described. The cyclopenta[a]phenanthrene skeleton is rapidly and efficiently assembled utilizing the Lewis acid-catalyzed Diels-Alder reaction of 1,2-dihydro-7-methoxy-4-vinylnaphthalene (5) with an alpha-heterosubstituted cyclopentenone, a "cyclopentynone" equivalent. It was found that the Diels-Alder reaction of alpha-(phenylselenenyl)- (6a) or alpha-bromocyclopentenone (6b) with 5 in the presence of 1.5 euqiv of SnCl4 followed by elimination with hydrogen peroxide or DBU produced the key intermediate 15,16-dihydro-3-methoxycyclopenta[a]phenanthren-17-one (10) in 28% or 59% overall yield, respectively. The synthesis of the A-ring metabolites features the use of a unique methoxime protecting group for the 17-ketone. The deprotection of the 17-methoxime group of the highly acid-sensitive 3,4-trans-dihydro 3,4-diol bis(TBDMS) ether 15b was achieved through the use of the low-valent titanium reagent produced upon reduction of TiCl3.3THF by DIBAL-H (51%). Treatment of bis-(TBDMS) ether 16 with TBAF in THF provided the desired 3,4-trans-dihydro 3,4-diol (3) (83%), thus achieving the synthesis of 3 in 10 steps in 9.6% overall yield from 6b. In addition, the bay-region syn-3,4-diol 1,2-epoxide (4a) was also synthesized from 3 in two steps [(1) NBA in 1:5 H2O/DMSO, (2) NaOMe/THF] in 59% overall yield.
• LEE, HOMGMEE;HARVEY, RONALD G., TETRAHEDRON. LETT., 29,(1988) N 26, 3207-3210
  作者：LEE, HOMGMEE、HARVEY, RONALD G.

  DOI：——

  日期：——
• LEE, HONGMEE;HARVEY, RONALD G., J. ORG. CHEM., 53,(1988) N 18, C. 4253-4256
  作者：LEE, HONGMEE、HARVEY, RONALD G.

  DOI：——

  日期：——