3-bromo-2-methyl-acrylic acid tert-butyl ester | 912809-59-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 3-bromo-2-methyl-acrylic acid tert-butyl ester
• 英文别名: 7,8-dimethyl-3-oxodeca-7,9-dienenitrile；tert-butyl (E)-3-bromo-2-methylacrylate；tert-butyl (2E)-3-bromo-2-methylprop-2-enoate；tert-butyl (E)-3-bromo-2-methylprop-2-enoate
• CAS: 912809-59-7
• 化学式: C₈H₁₃BrO₂
• 分子量: 221.094
• InChiKey: BLZTUHDREVWFEC-AATRIKPKSA-N

物化性质

• 沸点：
  218.8±23.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-2-methyl-acrylic acid tert-butyl ester 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 copper(l) iodide 、 palladium diacetate 、 silver carbonate 、 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.0h， 生成 (2E,4E)-6-hydroxy-2,4-dimethyl-hepta-2,4-dienoic acid t-butyl ester
  参考文献：
  名称：

  Sequential transhalogenation and Heck reaction for efficient access to dioxo-tetrasubstituted 2,4 E,E-dienes: synthesis of segment C1–C6 of apoptolidin

  摘要：

  Efficient access to dioxo-tetrasubstituted 2,4 E,E-dienes is developed in three steps from commercially available starting materials via sequential trans halogenation and Heck reaction, which provides potentially useful synthons for the synthesis of a tetrasubstituted conjugated diene structure in complex molecules. Thereby, segment C1-C6 of apoptolidin is synthesized. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.058
• 作为产物：
  描述：

  甲基丙烯酸叔丁酯 在 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 3-bromo-2-methyl-acrylic acid tert-butyl ester
  参考文献：
  名称：

  PET探针[ 11 C]脱氢普伐他汀的合成，可能对研究肝脏中的OATP1B1和MRP2转运蛋白有用

  摘要：

  毒品运输者在各个器官中介导毒品的吸收和消灭；因此，了解转运蛋白在体内的功能将对确保体内系统的药物功效起关键作用。在这种情况下，我们基于钯（0）介导的快速C -[ [ C] [[ 11 C] dehydropravastatin）的设计和合成，这是一种新颖的PET探针，可用于评估OATP1B1和MRP2转运蛋白的功能。11 C]甲基化（即[ 11 C]甲基碘与硼中间体之间的快速交叉偶联）。

  DOI：

  10.1016/j.bmc.2012.04.051

文献信息

• Single‐Flask Multicomponent Palladium‐Catalyzed α,γ‐Coupling of Ketone Enolates: Facile Preparation of Complex Carbon Scaffolds
  作者：Michael Grigalunas、Per‐Ola Norrby、Olaf Wiest、Paul Helquist

  DOI：10.1002/anie.201505895

  日期：2015.9.28

  A three‐component palladium‐catalyzed reaction sequence has been developed in which γ‐substituted α,β‐unsaturated products are obtained in a single flask by an α‐alkenylation with either a subsequent γ‐alkenylation or γ‐arylation of a ketone enolate. Coupling of a variety of electronically and structurally different components was achieved in the presence of a Pd/Q‐Phos catalyst (2 mol %), usually

  已开发出一种三组分钯催化的反应序列，其中在单个烧瓶中通过α-烯基化以及随后的γ-烯基化或酮烯酸酯的γ-芳基化在单个烧瓶中获得γ-取代的α，β-不饱和产物。在Pd / Q-Phos催化剂（2 mol％）的存在下，通常在22°C时，各种电子和结构上不同的组件可以实现偶联，收率最高为85％。最重要的是，通过一种简单的操作即可代替使用多个反应，从而获得这些产品。
• α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation
  作者：Roger R. Nani、Sarah E. Reisman

  DOI：10.1021/ja401610p

  日期：2013.5.15

  An investigation of the intramolecular cyclopropanation reactions of alpha-diazo-beta-ketonitriles is reported. These studies reveal that alpha-diazo-beta-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor acceptor-substituted diazo substrates instead produce mixtures of C-H insertion and dimerization products. alpha-Diazo-beta-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the alpha-cyano-alpha-ketocyclopropane products are demonstrated to serve as substrates for S(N)2, S(N)2', and aldehyde cycloaddition reactions.
• Synthesis of [11C]dehydropravastatin, a PET probe potentially useful for studying OATP1B1 and MRP2 transporters in the liver
  作者：Ryosuke Ijuin、Tadayuki Takashima、Yasuyoshi Watanabe、Yuichi Sugiyama、Masaaki Suzuki

  DOI：10.1016/j.bmc.2012.04.051

  日期：2012.6

  efficacy in in vivo systems. In this context, we designed and synthesized [11C]dehydropravastatin, a novel PET probe that would be potentially useful for evaluation of the functions of the OATP1B1 and MRP2 transporters, based on the use of palladium(0)-mediated rapid C-[11C]methylation (viz., the rapid cross-coupling between [11C]methyl iodide and a boron intermediate).

  毒品运输者在各个器官中介导毒品的吸收和消灭；因此，了解转运蛋白在体内的功能将对确保体内系统的药物功效起关键作用。在这种情况下，我们基于钯（0）介导的快速C -[ [ C] [[ 11 C] dehydropravastatin）的设计和合成，这是一种新颖的PET探针，可用于评估OATP1B1和MRP2转运蛋白的功能。11 C]甲基化（即[ 11 C]甲基碘与硼中间体之间的快速交叉偶联）。
• Sequential transhalogenation and Heck reaction for efficient access to dioxo-tetrasubstituted 2,4 E,E-dienes: synthesis of segment C1–C6 of apoptolidin
  作者：Xiaojin Li、Xingzhong Zeng

  DOI：10.1016/j.tetlet.2006.07.058

  日期：2006.9

  Efficient access to dioxo-tetrasubstituted 2,4 E,E-dienes is developed in three steps from commercially available starting materials via sequential trans halogenation and Heck reaction, which provides potentially useful synthons for the synthesis of a tetrasubstituted conjugated diene structure in complex molecules. Thereby, segment C1-C6 of apoptolidin is synthesized. (c) 2006 Elsevier Ltd. All rights reserved.