isopropyl 1-bromonaphthalene-2-carboxylate | 719278-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: isopropyl 1-bromonaphthalene-2-carboxylate
• 英文别名: isopropyl 1-bromo-2-naphthoate；propan-2-yl 1-bromonaphthalene-2-carboxylate
• CAS: 719278-25-8
• 化学式: C₁₄H₁₃BrO₂
• 分子量: 293.16
• InChiKey: CVQHRPLXWXSIGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  isopropyl 1-bromonaphthalene-2-carboxylate 在 正丁基锂 、 ethylene diamine tetraacetic acid tetrasodium salt 、 sodium hydride 、 碳酸氢钠 、 magnesium 、 丙酮 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 70.83h， 生成 1-[1'-(9"-fluorenyl)-2'-naphthyl]-3-cyclopentenol
  参考文献：
  名称：

  Zirconocene dichloride complexes with a 1,2-naphthylidene bridge as catalysts for the polymerisation of ethylene and propylene

  摘要：

  Ansa-zirconocene dichloride complexes containing a 9-fluorenyl group at the 1-position of naphthalene and a 2-indenyl 12, 1-indenyl 13, or cyclopentadienyl 14 group at the 2-position of the naphthalene were synthesised and characterised. The molecular structures of the complexes have been determined by single crystal X-ray diffraction studies. After activation with excess methyl-alumoxane (MAO). the complexes were used as homogeneous catalysts for the homopolymerisation of ethylene and propylene. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.03.021
• 作为产物：
  描述：

  1-溴-2-萘甲酸 在 吡啶 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 isopropyl 1-bromonaphthalene-2-carboxylate
  参考文献：
  名称：

  Asymmetric Suzuki–Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos

  摘要：

  通过使用单手螺旋聚合物配体PQXphos，通过苯基硼酸与2,4-二甲基戊烷-3-基-1-卤代-2-萘酸酯进行Suzuki–Miyaura交叉偶联合成了轴向手性的1,1'-联苯基-2-羧酸酯。

  DOI：

  10.1039/c5cc01074h

文献信息

• Asymmetric Suzuki–Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos
  作者：Yuto Akai、Laure Konnert、Takeshi Yamamoto、Michinori Suginome

  DOI：10.1039/c5cc01074h

  日期：——

  Axially chiral 1,1′-biaryl-2-carboxylates were synthesized via Suzuki–Miyaura cross-coupling of 2,4-dimethylpentan-3-yl 1-halo-2-naphthoates with arylboronic acids with single-handed helical polymer ligands PQXphos.

  通过使用单手螺旋聚合物配体PQXphos，通过苯基硼酸与2,4-二甲基戊烷-3-基-1-卤代-2-萘酸酯进行Suzuki–Miyaura交叉偶联合成了轴向手性的1,1'-联苯基-2-羧酸酯。
• Enantiospecific synthesis of a planar chiral fluorenylzirconium ansa-metallocene: synthesis and structures of [1-(9-fluorenyl)- and [1-(1-methyl-9-fluorenyl)-2-(2-indenyl)naphthalene]zirconium dichloride
  作者：Robert W. Baker、Michael A. Foulkes、Peter Turner

  DOI：10.1039/a910246i

  日期：——

  an axially chiral fluorenyl ligand, (a-S)-10, which on reaction with ZrCl4 enantiospecifically provides the planar chiral ansa-zirconocene (p-S)-[1-(1-methyl-9-fluorenyl)-2-(2-indenyl)naphthalene]zirconium dichloride, (p-S)-8; single crystal X-ray structures have been determined for the racemic ansa-zirconocene rac-8 and the related Cs-symmetric ansa-zirconocene 7.

  Di-lithiation of +ac(R)-1-methyl-9-[2-(2-indenyl)-1-naphthyl]fluorene, +ac(R)-6, generates an axially chiral fluorenyl ligand, (a-S)-10, which on reaction with ZrCl4enantiospecifically提供平面手性柄型-zirconocene（对小号） - [1-（1-甲基- 9-芴基）-2-（2-茚基）萘]二氯化锆，（对小号） - 8 ; 已被确定为外消旋单晶X射线结构安莎-zirconocene外消旋- 8和相关Ç小号-对称安莎-锆茂 7。
• Palladium-Catalyzed [3 + 2] Annulation of Aryl Halides with 7-Oxa- and 7-Azabenzonorbornadienes via C(sp² or sp³)–H Activation
  作者：Xiaojiao Li、Xianting Pan、Zisong Qi、Xingwei Li

  DOI：10.1021/acs.orglett.2c03422

  日期：2022.12.16

  epoxy-5H-benzo[b]fluorenes, and their aza analogues have been accessed via palladium-catalyzed exo-selective [3 + 2] annulation between aryl halides and 7-oxa- and 7-azabenzonorbornadienes. The reaction is initiated by the oxidative addition of a carbon–halogen bond, with intramolecular C(sp2 or sp3)–H activation being a key step. The enantioselective version of the reaction was also briefly explored.

  通过钯催化的芳基卤化物和 7-oxa- 和 7 之间的外选择性 [3 + 2] 环化，获得了一系列环氧苯并 [ k ] 荧蒽、环氧 -5 H -苯并 [ b ] 芴及其氮杂类似物-氮杂苯并降冰片二烯。该反应由碳-卤键的氧化加成引发，分子内 C(sp 2或 sp 3 )-H 活化是关键步骤。还简要探讨了该反应的对映选择性版本。
• Zirconocene dichloride complexes with a 1,2-naphthylidene bridge as catalysts for the polymerisation of ethylene and propylene
  作者：Helmut G Alt、Robert W Baker、Mahmoud Dakkak、Michael A Foulkes、Marc O Schilling、Peter Turner

  DOI：10.1016/j.jorganchem.2004.03.021

  日期：2004.6

  Ansa-zirconocene dichloride complexes containing a 9-fluorenyl group at the 1-position of naphthalene and a 2-indenyl 12, 1-indenyl 13, or cyclopentadienyl 14 group at the 2-position of the naphthalene were synthesised and characterised. The molecular structures of the complexes have been determined by single crystal X-ray diffraction studies. After activation with excess methyl-alumoxane (MAO). the complexes were used as homogeneous catalysts for the homopolymerisation of ethylene and propylene. (C) 2004 Elsevier B.V. All rights reserved.
• Enantioselective Synthesis of Both Axially and Planar Chiral Ferrocenes via Axial-to-Planar Diastereoinduction
  作者：Yang An、Xiao-Yan Zhang、Ya-Nan Ding、Yuke Li、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/acs.orglett.2c02707

  日期：2022.10.14

  Ferrocenes with planar chirality have emerged as an important class of scaffolds for ligands in asymmetric catalysis; however, ferrocene molecules with polychiral structures have not been well explored. Herein, both axially and planar chiral ferrocenes were synthesized via palladium/chiral norbornene cooperative catalysis and axial-to-planar diastereoinduction. In this work, chiral norbornene was used

  具有平面手性的二茂铁已成为不对称催化中配体的重要一类支架。然而，具有多手性结构的二茂铁分子尚未得到很好的探索。在此，轴向和平面手性二茂铁均通过钯/手性降冰片烯协同催化和轴向-平面非对映诱导合成。在这项工作中，手性降冰片烯用于立体选择性地控制芳族轴向手性，并进一步选择性诱导二茂铁平面手性的 C(sp 2 )-H 活化。基于密度泛函理论计算，证实了手性降冰片烯与底物的催化模型和轴向-平面非对映诱导过程。