1-bromo-2-[1-(4-chlorophenyl)ethenyl]-4-methoxybenzene | 1134949-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-bromo-2-[1-(4-chlorophenyl)ethenyl]-4-methoxybenzene
• 英文别名: 1-Bromo-2-[1-(4-chlorophenyl)ethenyl]-4-methoxybenzene
• CAS: 1134949-17-9
• 化学式: C₁₅H₁₂BrClO
• 分子量: 323.617
• InChiKey: CMIVUHCLSYFCGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-2-[1-(4-chlorophenyl)ethenyl]-4-methoxybenzene 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.41h， 生成 2-[1-(4-chlorophenyl)ethenyl]-4-methoxy-1-(methylsulfonyl)benzene
  参考文献：
  名称：

  An Efficient Synthesis of 4-Mono- and 4,4-Di-substituted 3,4-Dihydro-2H-1-benzothiopyran 1,1-Dioxides by LDA-Mediated Cyclization of o-(Methylsulfonyl)styrenes

  摘要：

  A new and efficient method for the preparation of 3,4-dihydro-2H-1-benzothiopyran 1,1-dioxide derivatives has been developed. alpha-Substituted o-(methylsulfonyl)styrenes, which can be derived from alpha-substituted o-bromostyrenes by an easily operated two-step sequence, are cyclized on treatment with lithium diisopropylamide (LDA) to give, after aqueous workup, the corresponding 4-monosubstituted 3,4-dihydro-2H-1-benzothiopyran 1,1-dioxides. Addition of electrophiles prior to aqueous workup provides 4,4-disubstituted derivatives.

  DOI：

  10.3987/com-18-13959
• 作为产物：
  描述：

  (2-溴-5-甲氧基苯基)(4-氯苯基)甲酮 、 亚甲基三苯基膦烷 以 四氢呋喃 为溶剂， 以90%的产率得到1-bromo-2-[1-(4-chlorophenyl)ethenyl]-4-methoxybenzene
  参考文献：
  名称：

  Synthesis of 2-Benzothiophene-1(3H)-thione and Isothiochromene-1-thione Derivatives by Iodine-Mediated Cyclization of Lithium 2-(Vinyl)dithiobenzoate Derivatives

  摘要：

  DOI：

  10.3987/com-08-11514

文献信息

• New, Facile Synthesis of 3,3-Disubstituted Phthalides Based on the Reaction of α-Substituted 2-Lithiostyrenes with Carbon Dioxide
  作者：Kazuhiro Kobayashi、Taketoshi Kozuki、Shuhei Fukamachi、Hisatoshi Konishi

  DOI：10.3987/com-09-11837

  日期：——

  A new method to prepare 3,3-disubstituted phthalides [isobenzofuran-1(3H)-ones] from alpha-substituted 2-bromostyrenes has been developed. The reaction of alpha-substituted 2-lithiostyrenes, generated in situ by bromine-lithium exchange between alpha-substituted 2-bromostyrenes and butyllithium, with carbon dioxide gave the corresponding lithium 2-vinylbenzoates, which upon treatment with concentrated hydrochloric acid afforded the desired products in one pot.
• Synthesis of 2H-Benzo[b]thietes by TFA-Mediated Cyclization of O-tert-Butyl S-(2-Vinylphenyl) Carbonothioates via 4H-3,1-Benzoxathiin-2-one Intermediates
  作者：Kazuhiro Kobayashi、Takuma Ueyama

  DOI：10.3987/com-18-14021

  日期：——

  An efficient method for the preparation of 2H-benzo[b]thiete derivatives under mild conditions has been developed. The reaction of 2-(1-arylethenyl)phenyl bromides with butyllithium at -78 degrees C generates 2-(1-arylethenyl)phenyllithiums, which are successively treated with sulfur and Boc(2)O at the same temperature to afford S-[2-(1-arylethenyl)phenyl] O-tert-butyl carbonothioates. These compounds are then treated with TFA at 0 or 20 degrees C to yield 2-aryl-2-methyl-2H-benzo[b]thietes via formation of the 4-aryl-4-methyl-4H-3,1-benzoxathiin-2-ones followed by decarboxylation.
• Synthesis of 2-Benzothiophene-1(3H)-thione and Isothiochromene-1-thione Derivatives by Iodine-Mediated Cyclization of Lithium 2-(Vinyl)dithiobenzoate Derivatives
  作者：Kazuhiro Kobayashi、Shuhei Fukamachi、Hisatoshi Konishi

  DOI：10.3987/com-08-11514

  日期：——
• An Efficient Synthesis of 4-Mono- and 4,4-Di-substituted 3,4-Dihydro-2H-1-benzothiopyran 1,1-Dioxides by LDA-Mediated Cyclization of o-(Methylsulfonyl)styrenes
  作者：Kazuhiro Kobayashi、Takuma Ueyama

  DOI：10.3987/com-18-13959

  日期：——

  A new and efficient method for the preparation of 3,4-dihydro-2H-1-benzothiopyran 1,1-dioxide derivatives has been developed. alpha-Substituted o-(methylsulfonyl)styrenes, which can be derived from alpha-substituted o-bromostyrenes by an easily operated two-step sequence, are cyclized on treatment with lithium diisopropylamide (LDA) to give, after aqueous workup, the corresponding 4-monosubstituted 3,4-dihydro-2H-1-benzothiopyran 1,1-dioxides. Addition of electrophiles prior to aqueous workup provides 4,4-disubstituted derivatives.