1-bromo-2-(1-(4-methoxyphenyl)prop-1-en-1-yl)benzene | 1214272-63-5

• 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-methoxyphenyl)prop-1-en-1-yl)benzene
• 英文别名: 1-bromo-2-[1-(4-methoxyphenyl)prop-1-enyl]benzene
• CAS: 1214272-63-5
• 化学式: C₁₆H₁₅BrO
• 分子量: 303.198
• InChiKey: FPHNRACCTVJBDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 1-bromo-2-(1-(4-methoxyphenyl)prop-1-en-1-yl)benzene 在 正丁基锂 、 盐酸 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以75%的产率得到3-ethyl-3-(4-methoxyphenyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  New, Facile Synthesis of 3,3-Disubstituted Phthalides Based on the Reaction of α-Substituted 2-Lithiostyrenes with Carbon Dioxide

  摘要：

  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.

  DOI：

  10.3987/com-09-11837
• 作为产物：
  描述：

  (2-溴苯基)(4-甲氧基苯基)甲酮 、 亚乙基三苯基膦 以 四氢呋喃 为溶剂， 以61%的产率得到1-bromo-2-(1-(4-methoxyphenyl)prop-1-en-1-yl)benzene
  参考文献：
  名称：

  New, Facile Synthesis of 3,3-Disubstituted Phthalides Based on the Reaction of α-Substituted 2-Lithiostyrenes with Carbon Dioxide

  摘要：

  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.

  DOI：

  10.3987/com-09-11837

文献信息

• Cobalt-Catalyzed Enantio- and Diastereoselective Intramolecular Hydroacylation of Trisubstituted Alkenes
  作者：Junfeng Yang、Alice Rérat、Yang Jie Lim、Corinne Gosmini、Naohiko Yoshikai

  DOI：10.1002/anie.201611518

  日期：2017.2.20

  Enantio‐ and diastereoselective synthesis of trans‐2,3‐disubstituted indanones is achieved by intramolecular hydroacylation of 2‐alkenylbenzaldehydes bearing trisubstituted alkenyl groups under cobalt‐chiral diphosphine catalysis. Notably, a high level of enantioselectivity is induced regardless of the stereochemistry (E/Z ratio) of the alkenyl group of the starting material. Deuterium‐labeling experiments

  对映体和非对映体选择性合成反式-2,3-二取代的茚满酮是通过在钴-手性二膦催化下将带有三取代烯基的2-烯基苯甲醛分子内加氢酰化而实现的。值得注意的是，无论原料的烯基的立体化学（E / Z比）如何，都诱导出高水平的对映选择性。氘标记实验阐明了E和Z异构体的有效反应途径。
• Pd-catalyzed intermolecular consecutive double Heck reaction “on water” under air: facile synthesis of substituted indenes
  作者：Dong Wei、Han-Yu Lu、Han-Zhe Miao、Chen-Guo Feng、Guo-Qiang Lin、Yingbin Liu

  DOI：10.1039/d3ra03510g

  日期：——

  An efficient and environmentally benign method for the preparation of substituted indene derivatives has been developed by using water as the sole solvent. This reaction proceeded under air, tolerated a wide range of functional-groups and was easily scaled up. Bioactive natural products like indriline were synthesized via the developed protocol. Preliminary results demonstrate that the enantioselective

  通过使用水作为唯一溶剂，开发了一种有效且环境友好的制备取代茚衍生物的方法。该反应在空气下进行，可耐受多种官能团，并且很容易扩大规模。通过开发的方案合成了像 indriline 这样的生物活性天然产物。初步结果表明，也可以实现对映选择性变体。
• Convenient Synthesis of 1,3-Dihydroisobenzofurans by Hydriodic Acid-Catalyzed Cyclization of 2-Vinylbenzyl Alcohols
  作者：Kazuhiro Kobayashi、Kazuaki Shikata、Yuri Fujii、Shuhei Fukamachi、Miyuki Tanmatsu、Hisatoshi Konishi

  DOI：10.3987/com-10-11947

  日期：——

  A new and short process has been developed for the preparation of 1,1,3-tri- and 1,1,3,3-tetra-substituted 1,3-dihydroisobenzofurans (phthalanes) from alpha-substituted 2-bromostyrenes. The method involves addition of a-substituted 2-lithiostyrenes, generated by the bromine-lithium exchange between alpha-substituted 2-bromostyrenes and butyllithium, to aliphatic aldehydes or ketones, followed by hydriodic acid catalyzed cyclization of the resulting 2-vinylbenzyl alcohols.