methyl 2-(bromomethyl)-3-(2-bromophenyl)prop-2-enoate | 1246014-43-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 2-(bromomethyl)-3-(2-bromophenyl)prop-2-enoate
• CAS: 1246014-43-6
• 化学式: C₁₁H₁₀Br₂O₂
• 分子量: 334.007
• InChiKey: NJJCKIHBFPJBSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  methyl 2-(bromomethyl)-3-(2-bromophenyl)prop-2-enoate 在 indium 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 (4S,5S)-4-(2-bromophenyl)-5-(3-methoxy-4-phenylmethoxyphenyl)-3-(piperidin-1-ylmethyl)oxolan-2-one
  参考文献：
  名称：

  WO2023/150719

  摘要：

  公开号：
• 作为产物：
  描述：

  methyl 2-((2-bromophenyl)(hydroxy)methyl)acrylate 在 氢溴酸 作用下， 以 水 为溶剂， 以92%的产率得到methyl 2-(bromomethyl)-3-(2-bromophenyl)prop-2-enoate
  参考文献：
  名称：

  Synthesis of dihydroindenofuran scaffold via a Pd-catalyzed 5-endo-trig cyclization/enolate O-alkylation cascade

  摘要：

  An efficient synthesis of dihydroindenofurans was carried out starting from the Baylis-Hillman adducts via a Pd-catalyzed 5-endo-trig-carbopalladation and enolate O-alkylation cascade as a key step. This is the first example of enolate O-alkylation with a C(sp(3))-bound palladium intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.127

文献信息

• A straightforward and convenient synthesis of functionalized allyl thiosulfonates and allyl disulfanes
  作者：Raju Jannapu Reddy、Md. Waheed、Jangam Jagadesh Kumar

  DOI：10.1039/c8ra06938g

  日期：——

  eco-friendly method has been developed for the synthesis of allyl thiosulfonates using Morita–Baylis–Hillman (MBH) allyl bromides and sodium arylthiosulfonates, which were readily assembled without any reagent/catalyst. Moreover, the allyl thiosulfonates were successfully transformed into a set of two synthetically viable diallyl disulfanes and unsymmetrical allyl disulfanes in the presence of Cs2CO3. The present

  已经开发出一种实用、高度灵活且环保的方法，用于使用 Morita-Baylis-Hillman (MBH) 烯丙基溴和芳基硫代磺酸钠合成烯丙基硫代磺酸盐，无需任何试剂/催化剂即可轻松组装。此外，在Cs 2 CO 3存在下，烯丙基硫代磺酸盐成功地转化为一组两种合成可行的二烯丙基二硫烷和不对称烯丙基二硫烷。本协议在操作上简单方便，可生成多种功能化的烯丙基硫代磺酸盐和烯丙基二硫烷，产率良好。
• Regioselective Synthesis of Functionalized Oxime Ethers
  作者：Jun Liu、Dafeng Li、Jian Li、Chunju Li、Xueshun Jia

  DOI：10.2174/157017810791824874

  日期：2010.9.1

  We report in this paper the regioselective synthesis of functionalized oxime ethers 3 in good yields from the reaction of readily available starting material oximes with allyl bromides, derived from Baylis-Hillman adducts, in the presence of sodium hydride and triethyl amine under mild condition.

  我们在本文中报告了在氢化钠和三乙胺的存在下，利用易得的起始材料肟与烯丙基溴（从 Baylis-Hillman 加合物中提取）在温和条件下的反应，以良好的收率选择性地合成了官能化的肟醚 3。
• Ester-directed orthogonal dual C–H activation and <i>ortho</i> aryl C–H alkenylation <i>via</i> distal weak coordination
  作者：Manickam Bakthadoss、Tadiparthi Thirupathi Reddy、Vishal Agarwal、Duddu S. Sharada

  DOI：10.1039/d1cc06097j

  日期：——

  of two same molecules via dual C–H bond activation in an intermolecular fashion has been developed using a distal ester-directing group. This new coupling reaction led to the synthesis of the highly functionalized 1,3-diaryl molecular architecture in very good yields and with high chemo- and regioselectivities. In addition, using ester as the distal directing group, ortho C–H olefination of α-methyl

  使用远端酯导向基团，通过分子间方式的双 C-H 键活化，在两个相同分子的芳族 C(sp 2 ) 和脂族烯烃 C(sp 2 ) 碳之间进行了前所未有的正交交叉偶联。这种新的偶联反应导致以非常好的收率和高化学和区域选择性合成高度官能化的 1,3-二芳基分子结构。此外，使用酯作为远端导向基团， α-甲基芳基丙烯酸酯和肉桂酸酯与各种烯烃的邻位C-H 烯化反应以非常好的收率和广泛的底物范围实现。
• One‐Pot Synthesis of α‐Diazo‐γ,δ‐unsaturated Esters as Versatile Building Blocks for Functionalized Dienes, Cyclopentenes, and 5,7‐Fused Bicycles
  作者：Theo V. C. Russo、Marcus M. Sá

  DOI：10.1002/ejoc.202100797

  日期：2021.8.6

  The synthesis of novel allylic α-diazo carbonyl compounds was readily achieved through a one-pot strategy involving base-catalyzed allylation of 1,3-dicarbonyls followed by the deacylative diazo transfer reaction. The synthetic versatility of α-diazo esters was demonstrated through rhodium-catalyzed transformations, where the type of product formed (cyclopentene, 5,7-fused bicycle, diene) is dependent

  新型烯丙基 α-重氮羰基化合物的合成很容易通过一锅法实现，包括碱催化 1,3-二羰基的烯丙基化，然后是脱酰基重氮转移反应。α-重氮酯的合成多功能性通过铑催化的转化得到证明，其中形成的产物类型（环戊烯、5,7-稠合双烯、二烯）取决于所用的底物和催化剂。
• Natural product inspired design and synthesis of β-carboline and γ-lactone based molecular hybrids
  作者：Dharmender Singh、Nisha Devi、Vipin Kumar、Chandi C. Malakar、Saloni Mehra、Sunita Rattan、Ravindra K. Rawal、Virender Singh

  DOI：10.1039/c6ob01216g

  日期：——

  to execute single-step tandem Barbier type allylation–lactonisation process has been devised in order to afford the targeted molecular architectures. It is anticipated that aqueous medium plays the key role in allylation as well as in the subsequent lactonisation process for the diastereo-selective synthesis of these conjugates. It is believed that water drives the reaction pathway through dual activation

  β-Carboline和γ-lactone部分已被自然界选作特有的支架，并具有广泛的药理特性。根据自然界，我们设想了结合了这两个药效基团的新型基于β-咔啉和γ-内酯的分子杂合物的制备。在这方面，已经设计了一种水辅助的介导的环境良性且易于执行的单步串联Barbier型烯丙基化-内酯化工艺，以提供目标分子结构。预期水性介质在烯丙基化以及随后的内酯​​化过程中对于这些缀合物的非对映选择性合成起关键作用。人们相信水会通过双重激活来驱动反应路径，原位分子内凝结。重要的是，在该合成策略中，在任何阶段都不需要柱色谱纯化。