1-苄基-2-乙烯基苯 | 132884-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苄基-2-乙烯基苯
• 英文名称: 1-benzyl-2-vinylbenzene
• 英文别名: Benzene, 1-ethenyl-2-(phenylmethyl)-；1-benzyl-2-ethenylbenzene
• CAS: 132884-19-6
• 化学式: C₁₅H₁₄
• 分子量: 194.276
• InChiKey: SDRWHLXPMAUNPK-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1-苄基-2-乙烯基苯 在 potassium tert-butylate 、 甲基锂 作用下， 以 乙醚 、 正己烷 、 叔丁醇 、 正戊烷 为溶剂， 生成 1-(o-benzylphenyl)allene
  参考文献：
  名称：

  Photochemistry of 1-phenyl-1,2-dihydronaphthalene in methanol

  摘要：

  The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated. The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclo[3.1.0]hex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular [4 + 2] photocycloaddition reaction leading to exo-2. The experimental results can be rationalized by assuming that this photoprocess involves a concerted pi-4a + pi-2a-type electrocyclic reaction. cis-Dibenzobicyclo[3.3.0]octa-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement. On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1. The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions. Irradiation of 1 at 254 nm yields 8 as the only photoproduct. Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level. A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.

  DOI：

  10.1021/jo00007a033
• 作为产物：
  描述：

  2-苄基苯甲酸 在 正丁基锂 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 0.02h， 生成 1-苄基-2-乙烯基苯
  参考文献：
  名称：

  Photochemistry of 1-phenyl-1,2-dihydronaphthalene in methanol

  摘要：

  The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated. The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclo[3.1.0]hex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular [4 + 2] photocycloaddition reaction leading to exo-2. The experimental results can be rationalized by assuming that this photoprocess involves a concerted pi-4a + pi-2a-type electrocyclic reaction. cis-Dibenzobicyclo[3.3.0]octa-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement. On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1. The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions. Irradiation of 1 at 254 nm yields 8 as the only photoproduct. Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level. A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.

  DOI：

  10.1021/jo00007a033

文献信息

• A Convenient Method for the Synthesis of 2-Arylaziridines from Styrene Derivatives via 2-Arylethenyl(diphenyl)sulfonium Salts
  作者：Jun-ichi Matsuo、Hiroyuki Yamanaka、Asahi Kawana、Teruaki Mukaiyama

  DOI：10.1246/cl.2003.392

  日期：2003.4

  Styrene derivatives reacted with diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1) at low temperature to afford 2-arylethenyl(diphenyl)sulfonium triflates (2). Treatment of 2 with primary amines gave the corresponding 2-arylaziridines in high yields. One-pot synthesis of various aziridines was also successfully carried out without isolation of the intermediate 2.

  苯乙烯衍生物在低温下与二苯基（三氟甲磺酰氧基）锍三氟甲磺酸盐（1）反应，生成2-芳基乙烯基（二苯基）锍三氟甲磺酸盐（2）。将2与一级胺反应，可高产率地得到相应的2-芳基氮杂环丙烷。多种氮杂环丙烷的一锅法合成也成功实现，无需分离中间体2。
• [EN] SECOND GENERATION GRP94-SELECTIVE INHIBITORS<br/>[FR] INHIBITEURS SÉLECTIFS DE GRP94 DE SECONDE GÉNÉRATION
  申请人：UNIV KANSAS

  公开号：WO2019040792A1

  公开（公告）日：2019-02-28

  The present technology provides compounds selective for the Grp94 isoform, as well as compositions including such compounds, that are useful for treatment of multiple myeloma, melanoma, lung cancer, hepatocellular carcinoma, breast cancer, prostate cancer, and/or glaucoma. Methods using the compounds are also provided.

  目前的技术提供了选择性作用于Grp94亚型的化合物，以及包括这些化合物的组合物，这些化合物对于治疗多发性骨髓瘤、黑色素瘤、肺癌、肝细胞癌、乳腺癌、前列腺癌和/或青光眼等疾病是有用的。同时还提供了使用这些化合物的方法。
• Second Generation Grp94-Selective Inhibitors Provide Opportunities for the Inhibition of Metastatic Cancer
  作者：Vincent M. Crowley、Dustin J. E. Huard、Raquel L. Lieberman、Brian S. J. Blagg

  DOI：10.1002/chem.201703398

  日期：2017.11.7

  the 90 kDa heat shock protein (Hsp90) family and its inhibition represents a promising therapeutic target for the treatment of many diseases. Modification of the first generation cis‐amide bioisostere imidazole to alter the angle between the resorcinol ring and the benzyl side chain via cis‐amide replacements produced compounds with improved Grp94 affinity and selectivity. Structure–activity relationship

  葡萄糖调节蛋白94（Grp94）是90 kDa热休克蛋白（Hsp90）家族的内质网（ER）常驻同工型，其抑制作用代表了治疗许多疾病的有希望的治疗靶标。修改第一代顺式酰胺生物同工甾醇咪唑，通过顺式酰胺替代来改变间苯二酚环与苄基侧链之间的夹角，从而制得了具有改善的Grp94亲和力和选择性的化合物。结构-活性关系研究导致发现化合物30，该化合物表现为540 n m对Grp94的亲和力和73倍的选择性。Grp94负责与细胞信号传导和运动相关的蛋白质（包括选定的整联蛋白）的成熟和运输。研究表明，Grp94选择性抑制剂30对多种侵袭性和转移性癌症表现出有效的抗迁移作用。
• Palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehydes
  作者：Lan Lei、Ping Wu、Zhuqing Liu、Jiang Lou

  DOI：10.1016/j.tetlet.2021.152865

  日期：2021.3

  The palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehyde derivatives was achieved utilizing 2-dimethylaminoethylamine as a novel transient directing group. The γ-C(sp3)–H arylation reaction efficiently afforded a variety of arylated o-alkylbenzaldehydes and polycyclic aromatic hydrocarbons (PAHs) in one pot, exhibiting high functional group tolerance with broad substrate scope. The

  钯催化的邻烷基苯甲醛衍生物的苄基C（sp 3）-H芳基化反应是利用2-二甲基氨基乙胺作为新型的瞬态导向基团实现的。的γ -C（SP 3）-H的芳基化反应有效地得到各种芳基化Ó以一个锅煮-alkylbenzaldehydes和多环芳香烃（PAHs），表现出与广泛的底物范围高的官能团耐受性。脂族二胺助剂代表用于C H活化的简单，廉价，易于获得和可除去的导向基团。结果o在温和的条件下，可以将苄基苯甲醛产品多样化地转化为潜在重要的合成中间体。
• Tf2O-catalyzed Friedel–Crafts alkylation to synthesize dibenzo[a,d]cycloheptene cores and application in the total synthesis of Diptoindonesin D, Pauciflorial F, and (±)-Ampelopsin B
  作者：Gang-Wei Wang、Hong-Li Wang、David A. Capretto、Qi Han、Rong-Bin Hu、Shang-Dong Yang

  DOI：10.1016/j.tet.2012.03.073

  日期：2012.7

  By using Tf2O as a catalyst, we have developed a protocol for the preparation of various dibenzo[a,d]cycloheptene cores via Friedel–Crafts alkylation. Using this method as the key step, we also present concise and useful routes to synthesize the natural products Diptoindonesin D, Pauciflorial F, and (±)-Ampelopsin B. Notably, this process exhibited following very attractive features: (i) the process

  通过使用Tf 2 O作为催化剂，我们已经开发了通过Friedel-Crafts烷基化反应制备各种二苯并[ a，d ]环庚烯核的方案。使用此方法作为关键步骤，我们还提供了简洁实用的途径来合成天然产物Diptoindonesin D，洋紫苏F和（±）-AmpelopsinB。值得注意的是，该过程具有以下非常吸引人的特征：不含金属，仅使用催化量的Tf 2 O，并且（ii）该方法简单且环保，避免使用过量的碱，氧化剂或其他添加剂。