5-phenyl-2,3-dihydro-1H-cyclopenta[a]naphthalene | 81396-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-phenyl-2,3-dihydro-1H-cyclopenta[a]naphthalene
• CAS: 81396-16-9
• 化学式: C₁₉H₁₆
• 分子量: 244.336
• InChiKey: TVKLBASIDHBBBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (1S,5R,6R)-7,7-diphenylbicyclo[3.2.0]hept-2-en-6-ol 以10%的产率得到
  参考文献：
  名称：

  LEE-RUFF, E.;HOPKINSON, A. C.;KAZARIANS-MOGHADDAM, H.;DUPERROUZEL, P.;GUP+, TETRAHEDRON LETT., 1981, 22, N 49, 4917-4920

  摘要：

  DOI：

文献信息

• A novel acid-catalyzed rearrangement of cyclobutanols
  作者：Edward Lee-Ruff、Alan C Hopkinson、Hira Kazarians-Moghaddam、Paul Duperrouzel、Brij Gupta、Morris Katz

  DOI：10.1016/s0040-4039(01)92381-0

  日期：1981.1

  Under acid-catalysis 7-arylbicyclo[3.2.0]hept-2-en-6-ols rearrange to diarylmethanes and cyclopenteno-annelated polycyclic aromatic hydrocarbons.

  在酸催化下，7-芳基双环[3.2.0] hept-2-en-6-ols重排为二芳基甲烷和环戊烯基退火的多环芳烃。
• Acid-catalyzed rearrangement of cyclobutanols. Syntheses of chrysenes, cyclopentenophenanthrenes, and diarylmethanes
  作者：Edward Lee-Ruff、Alan C. Hopkinson、Hira Kazarians-Moghaddam、Brij Gupta、Morris Katz

  DOI：10.1139/v82-026

  日期：1982.1.15

  Acid-catalyzed reactions of 8-aryl or 8,8-diarylbicyclo[4.2.0]oct-2-en-7-ols lead to tetrahydrophenanthrene derivatives. For example 8-(1-naphthyl)-bicyclo[4.2.0]oct-2-en-7-ols give substituted chrysenes in methanesulphonic acid. In the case of the homologous 7-aryl or 7,7-diarylbicyclo[3.2.0]hept-2-en-6-ols a novel transformation to diarlymethanes is observed. A mechanism is proposed which accounts

  8-芳基或8,8-二芳基双环[4.2.0] oct-2-en-7-ols 的酸催化反应生成四氢菲衍生物。例如，8-(1-萘基)-双环[4.2.0]oct-2-en-7-ols 在甲磺酸中产生取代的芘。在同源 7-芳基或 7,7-二芳基双环 [3.2.0]hept-2-en-6-ols 的情况下，观察到了向二芳基甲烷的新转化。提出了一种机制来解释在这些重排中观察到的产物分布。
• Rhenium-catalyzed synthesis of naphthalene derivatives via insertion of aldehydes into a C–H bond
  作者：Yoichiro Kuninobu、Yuta Nishina、Kazuhiko Takai

  DOI：10.1016/j.tet.2007.05.083

  日期：2007.8

  A rhenium complex, [ReBr(CO)3(THF)]2, catalyzed reactions of aromatic ketimines and aldehydes with dienophiles, followed by dehydration, to give naphthalene derivatives in good to excellent yields. This reaction proceeds via C–H bond activation, insertion of an aldehyde, intramolecular nucleophilic cyclization, reductive elimination, elimination of aniline and Diels–Alder reaction. After dehydration

  complex络合物[ReBr（CO）3（THF）] 2催化芳香族酮亚胺和醛与亲二烯体的反应，然后进行脱水，从而以良好或极佳的收率得到萘衍生物。该反应通过C–H键活化，醛的插入，分子内亲核环化，还原消除，苯胺消除和Diels–Alder反应进行。脱水后，形成萘衍生物。
• Formation of Benzo-Fused Carbocycles by Formal Radical Cyclization onto an Aromatic Ring
  作者：Derrick L. J. Clive、Rajesh Sunasee

  DOI：10.1021/ol070849l

  日期：2007.7.1

  An indirect method for effecting radical carbocyclization onto aromatic rings is described. Cross-conjugated dienones such as 13, readily prepared by Birch reduction of aromatic tert-butyl esters, in situ alkylation, and oxidation (10 --> 11 --> 12 --> 13), undergo radical cyclization; the products (14) are aromatized by silylation, Saegusa oxidation, and treatment with BiCl3.H2O. A noteworthy feature

  描述了一种实现自由基碳环化到芳族环上的间接方法。交联二烯酮（如13）可通过桦木还原芳香叔丁酯，原位烷基化和氧化（10-> 11-> 12-> 13）制得，并进行自由基环化。通过甲硅烷基化，Saegusa氧化和BiCl3.H2O处理将产品（14）芳香化。该路线的一个值得注意的特征是它提供了将额外的取代基连接到原始芳香环上的机会。
• Formal radical closure onto aromatic rings—a general route to carbocycles
  作者：Derrick L. J. Clive、Rajesh Sunasee、Zhenhua Chen

  DOI：10.1039/b803308k

  日期：——

  A general method is described for indirectly effecting radical carbocyclization of an alkyl chain onto an aromatic ring. Birch reductive-alkylation of aromatic tert-butyl esters with α,ω-dibromides, chromium(VI)-mediated oxidation of the resulting 1,4-dienes and Finkelstein displacement of Br− with NaI gives cross-conjugated ketones that undergo radical cyclization. The products are easily aromatized to phenols by silylation, Saegusa oxidation and treatment with BiCl3.H2O. A special feature of the route is that it allows attachment of a substituent to the original aromatic ring in place of the phenolic oxygen of the normal product.

  一种通用方法被描述用于间接地实现烷基链与芳环的自由基碳环化。通过使用α,ω-二溴化物对芳香叔丁基酯进行Birch还原烷基化，接着对所得的1,4-二烯进行铬(VI)介导的氧化，以及用NaI替代Br⁻的Finkelstein反应，可以得到交联共轭酮，这些酮随后经历自由基环化。这些产物可以通过硅化、Saegusa氧化以及与BiCl3·H2O处理，轻松芳香化为酚类化合物。这条路线的一个特殊之处在于，它允许将取代基附加到原始芳环上，以替代正常产物中的酚醇氧。