1-bromo-2-(3-oxopropyl)naphthalene | 153165-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-2-(3-oxopropyl)naphthalene
• 英文别名: 3-(1-bromo-2-naphthalyl)propanal；1-Bromo-2-naphthalenepropanal；3-(1-Bromonaphthalen-2-yl)propanal
• CAS: 153165-17-4
• 化学式: C₁₃H₁₁BrO
• 分子量: 263.134
• InChiKey: QGYPRPQGISPHQR-UHFFFAOYSA-N

物化性质

• 沸点：
  369.3±17.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-2-(3-oxopropyl)naphthalene 在 偶氮二异丁腈 、 三正丁基氢锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 甲苯 为溶剂， 反应 0.25h， 生成 2,3-dihydro-1-((methoxycarbonyl)methyl)benzindene
  参考文献：
  名称：

  Synthetic studies of the tandem enediyne-mono- and bisradical cyclizations

  摘要：

  The readily synthesized enediynes 12a-j possessing a tethered olefin radical acceptor can participate in a tandem enediyne-radical cyclization to yield dibydrobenzindene derivatives 14a-j. In the present study, the scope of this reaction was expanded to include a wide variety of olefin acceptors. Substitution at both ends of olefin leads to the formation of two diastereomers 14b and 14c in a 3.5:1 ratio when R3 is Me and R2 is CO2Me. The structures of the dihydrobenzindene products 14b and 14c were confirmed by generating a radical from 25 by a tributyltin hydride reaction which undergoes radical cyclization; this radical is similar to the enediyne-generated radical, which also cyclizes. It was shown that, in 14i and 14j, a substituent at R1 slowed the reaction but still resulted in a good to excellent yield of product. A tandem enediyne-6-exo-radical cyclization of 16 was also carried out but did not work as well as its 5-exo counterpart 12a. Finally, an enediyne 33 containing two olefinic tethers was cyclized in a process to form tetracycle 34 where three rings were formed in one synthetic operation.

  DOI：

  10.1021/ja00078a013
• 作为产物：
  描述：

  β-(1-Bromo-2-naphthyl)propionic Acid 在 2,2,6,6-四甲基哌啶氧化物 、 dimethyl sulfide borane 、 三氯异氰尿酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.42h， 生成 1-bromo-2-(3-oxopropyl)naphthalene
  参考文献：
  名称：

  通过Gold（I）催化轻松制得的氢乙炔。

  摘要：

  基于Au（I）催化的1,7-烯炔的环化反应，已经开发了一种合成部分饱和并苯衍生物的新策略。该方法可直接获得具有并苯系列骨架（直至并苯）的稳定多环产物。

  DOI：

  10.1002/anie.201604952

文献信息

• The tandem bergman-radical cyclization: a new method for ring annulation
  作者：Janet Wisniewski Grissom、Trevor L. Calkins

  DOI：10.1016/s0040-4039(00)74199-2

  日期：1992.4

  Heading of enediynes 1a, 1b and 2 at 210° C in a sealed tube in the presence of a hydrogen atom source yields naphthalene derivatives 3a, 3b and 4 in yields of 53-72%.

  在氢原子源的存在下，在密封管中于210℃下对苯二炔1a，1b和2的抽头，得到萘衍生物3a，3b和4，产率为53-72％。
• Synthesis and Photochemical Investigations of Tetrasubstituted Alkenes as Molecular Switches-The Effect of Substituents
  作者：Lutz F. Tietze、M. Alexander Düfert、Tim Hungerland、Kawon Oum、Thomas Lenzer

  DOI：10.1002/chem.201003559

  日期：2011.7.18

  Molecular switches based on helical tetrasubstituted alkenes, substituted with either electron‐withdrawing (CF3, F, CN; 2 a–c, 3 a,c) or ‐donating substituents (Me, OMe; 2 d,e), have been synthesized from acyclic precursors 4 and 5 in a domino carbopalladation/Stille reaction. This palladium‐catalyzed process allowed the rapid assembly of two CC bonds, two six‐membered rings, and the tetrasubstituted

  合成了基于螺旋四取代烯烃的分子开关，这些分子被吸电子（CF 3，F，CN; 2 a – c，3 a，c）或给体取代基（Me，OMe; 2 d，e）取代在多米诺骨腕/ Stille反应中由无环前体4和5合成。此钯催化的过程允许的两个C快速组装C键，两个六元环和完全取代的非对映选择性方式的四取代双键。通过交替照射两个不同的波长区域，研究了取代基对整个转换过程的电子效应。尽管取代基对吸收最大值的影响很小，但观察到开关行为的巨大差异。
• Synthesis of Chiroptical Molecular Switches by Pd-Catalyzed Domino Reactions
  作者：Lutz F. Tietze、Alexander Düfert、Florian Lotz、Lars Sölter、Kawon Oum、Thomas Lenzer、Tobias Beck、Regine Herbst-Irmer

  DOI：10.1021/ja906260x

  日期：2009.12.16

  New photochromic switches based on helical alkenes can quickly and efficiently be accessed by Pd-catalyzed domino reactions using a modular approach; this allows a wide variability in product formation with the advantages of a convergent synthetic route. The alkenes have been synthesized in excellent enantioselectivity and their switching properties assessed by stimulation with nanosecond laser pulses

  基于螺旋烯烃的新型光致变色开关可以使用模块化方法通过 Pd 催化的多米诺反应快速有效地获得；这允许具有收敛合成路线的优势的产品形成的广泛可变性。烯烃以优异的对映选择性合成，并通过在超过 1000 次开关循环中使用两种不同波长的纳秒激光脉冲进行刺激来评估它们的开关特性。
• Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors
  作者：Janet Wisniewski Grissom、Detlef Klingberg、Sabine Meyenburg、Brenda L. Stallman

  DOI：10.1021/jo00104a053

  日期：1994.12

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.
• Hydroacenes Made Easy by Gold(I) Catalysis
  作者：Ruth Dorel、Paul R. McGonigal、Antonio M. Echavarren

  DOI：10.1002/anie.201604952

  日期：2016.9.5

  A novel strategy for the synthesis of partially saturated acene derivatives has been developed based on a Au(I) -catalyzed cyclization of 1,7-enynes. This method provides straightforward access to stable polycyclic products featuring the backbone of the acene series, up to nonacene.

  基于Au（I）催化的1,7-烯炔的环化反应，已经开发了一种合成部分饱和并苯衍生物的新策略。该方法可直接获得具有并苯系列骨架（直至并苯）的稳定多环产物。