2-(cyclobutylidenemethyl)naphthalene | 123752-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(cyclobutylidenemethyl)naphthalene
• CAS: 123752-02-3
• 化学式: C₁₅H₁₄
• 分子量: 194.276
• InChiKey: VZYZKIDEMGGAKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(cyclobutylidenemethyl)naphthalene 在 Iron(III) nitrate nonahydrate 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 乙腈 为溶剂， 以30%的产率得到naphthalen-2-yl(1-nitrocyclobutyl)methyl nitrate
  参考文献：
  名称：

  亚烷基环丙烷和亚烷基环丁烷的氧化官能化：获得硝化环丙烷和环丁烷的多功能平台

  摘要：

  Fe(NO 3 ) 3 ·9H 2 O 或 AgNO 2对亚烷基环丙烷 (ACPs) 和亚烷基环丁烷 (ACBs) 进行了不同的自由基硝化反应，得到 β-硝基醇、α-硝基酮和硝基亚硝化三类产品产率高达 90% 的产品。特别是，环丙基和环丁基环在产物中是保守的。通过放大实验和将硝基还原为氨基，证明了该方法的适用性。初步的机理研究表明，硝基自由基参与了反应过程。

  DOI：

  10.1039/d2ob01426b
• 作为产物：
  描述：

  环丁酮 、 (2-萘甲基)(三苯基)溴化膦 在 正丁基锂 作用下， 生成 2-(cyclobutylidenemethyl)naphthalene
  参考文献：
  名称：

  Photochemistry of axially chiral (arylmethylene)cycloalkanes: a search for suitable photoswitchable liquid crystalline materials

  摘要：

  A series of chiral (arylmethylene)cycloalkanes was synthesized in racemic and optically active form to examine their suitability for incorporation in a liquid crystal-based optical switch. Irradiation of these compounds with UV light leads to their rapid photoracemization and, in some cases, their simultaneous destruction. The absorption spectra and circular dichroism spectra of these optically active compounds were determined. Chiral exciton coupling theory proves to be a good guide for predicting the magnitude of DELTAepsilon and glambda, (the Kuhn anisotropy factor). Addition of the optically active (arylmethylene)cycloalkanes to nematic liquid crystal materials induces cholesteric behavior. The helical twisting power (beta(M)) was determined for each compound, and a limit of 90 mum was established for the detection of a long-pitch cholesteric liquid crystal. Irradiation of the cholesteric liquid crystals formed by addition of the optically active (arylmethylene)cycloalkanes induces the transition to a compensated nematic phase that is readily sensed by optical microscopy.

  DOI：

  10.1021/jo00053a021

文献信息

• Transition metal promoted reactions. 30. Cyclopropyl anion as an allyl anion synthon. Novel synthesis of butadienes by nickel-catalyzed coupling of cyclopropyl Grignard reagents with dithioacetals
  作者：Dennis K. P. Ng、Tien Yau Luh

  DOI：10.1021/ja00207a029

  日期：1989.12

  Resolution of the reaction mixture and isolation of the triester product can be accomplished by using HPLC (4.6 X 250 mm Hypersil-ODS with 0.02 M KH2P04, pH 5.5, and a methanol gradient). Modification of the phosphorothioate was observed to be more efficient for the single-stranded d[CGCA(s)AAAAAGCG] fragment than the self-complementary eicosomer, d[CGTACTAGTT(s)AACTAGTACG] . This difference in reactivity

  反应混合物的拆分和三酯产物的分离可以通过使用HPLC（4.6 X 250 mm Hypersil-ODS，具有0.02 M KH 2 PO 4 ，pH 5.5和甲醇梯度）来完成。观察到硫代磷酸酯的修饰对于单链 d[CGCA(s)AAAAAGCG] 片段比自身互补的低分子异构体 d[CGTACTAGTT(s)AACTAGTACG] 更有效。当反应混合物在 50 ℃加热时，这种反应性差异被部分克服。在不存在硫代磷酸二酯的情况下，使用天然寡脱氧核苷酸的对照反应不会产生任何显着的标记。'2未标记的十二聚体螺旋，d [CGCA(s) AAAAAGCG].d[CGCTTTTTTGCG]，表现出的 T 为 55" C，这与 T 无法区分，PROXYL 标记（图 1 中的 a）或药物标记（图 1 中的 b）螺旋获得的值。与未标记的片段（T ，= 67”C）相比，具有两个标记的自身互补的ε-异构体 d[CG
• Fluorination of alkylidenecyclopropanes and alkylidenecyclobutanes: divergent synthesis of fluorinated cyclopropanes and cyclobutanes
  作者：Jin-Bo Wu、Shuang Li、Shuai Han、Yue Wang、Wei Zhang、Zhen Wang、Yao-Fu Zeng

  DOI：10.1039/d3ob00785e

  日期：——

  A divergent fluorination of alkylidenecyclopropanes (ACPs) and alkylidenecyclobutanes (ACBs) with selectfluor has been achieved. Four different types of products including fluorohydrins, fluoroethers, fluoroesters and fluoroketones could be prepared in moderate to excellent yields. In particular, the cyclopropanes and cyclobutanes were not destroyed during the transformations which involved a radical

  亚烷基环丙烷 (ACP) 和亚烷基环丁烷 (ACB) 与 selectflu 的不同氟化反应已经实现。可以以中等至优异的产率制备四种不同类型的产品，包括氟代醇、氟代醚、氟代酯和氟代酮。特别是，环丙烷和环丁烷在涉及自由基途径的转化过程中没有被破坏。通过产品的各种转化证明了该方法的适用性。
• Enantioselective Synthesis of 2-Aryl Cyclopentanones by Asymmetric Epoxidation and Epoxide Rearrangement
  作者：Yu-Mei Shen、Bin Wang、Yian Shi

  DOI：10.1002/anie.200501520

  日期：2006.2.20
• Photochemistry of axially chiral (arylmethylene)cycloalkanes: a search for suitable photoswitchable liquid crystalline materials
  作者：Robert P. Lemieux、Gary B. Schuster

  DOI：10.1021/jo00053a021

  日期：1993.1

  A series of chiral (arylmethylene)cycloalkanes was synthesized in racemic and optically active form to examine their suitability for incorporation in a liquid crystal-based optical switch. Irradiation of these compounds with UV light leads to their rapid photoracemization and, in some cases, their simultaneous destruction. The absorption spectra and circular dichroism spectra of these optically active compounds were determined. Chiral exciton coupling theory proves to be a good guide for predicting the magnitude of DELTAepsilon and glambda, (the Kuhn anisotropy factor). Addition of the optically active (arylmethylene)cycloalkanes to nematic liquid crystal materials induces cholesteric behavior. The helical twisting power (beta(M)) was determined for each compound, and a limit of 90 mum was established for the detection of a long-pitch cholesteric liquid crystal. Irradiation of the cholesteric liquid crystals formed by addition of the optically active (arylmethylene)cycloalkanes induces the transition to a compensated nematic phase that is readily sensed by optical microscopy.
• Oxidative functionalization of alkylidenecyclopropanes and alkylidenecyclobutanes: a versatile platform to access nitrated cyclopropanes and cyclobutanes
  作者：Yao-Fu Zeng、Jin-Bo Wu、Jin-Tao Chen、Yu Guo、Zhen Wang

  DOI：10.1039/d2ob01426b

  日期：——

  including β-nitro alcohol, α-nitro ketone and nitro nitratosation products with yields up to 90%. Particularly, the cyclopropyl and cyclobutyl rings were conserved in the products. The applicability of this method was demonstrated by the scale-up experiment and reduction of the nitro into an amino group. Preliminary mechanistic studies suggested that the nitro radical was involved in the reaction process.

  Fe(NO 3 ) 3 ·9H 2 O 或 AgNO 2对亚烷基环丙烷 (ACPs) 和亚烷基环丁烷 (ACBs) 进行了不同的自由基硝化反应，得到 β-硝基醇、α-硝基酮和硝基亚硝化三类产品产率高达 90% 的产品。特别是，环丙基和环丁基环在产物中是保守的。通过放大实验和将硝基还原为氨基，证明了该方法的适用性。初步的机理研究表明，硝基自由基参与了反应过程。