methyl 4-bromo-2-methyl-but-2-enoate | 99968-60-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-bromo-2-methyl-but-2-enoate
• 英文别名: 4-bromo-2-methyl-but-2-enoic acid methyl ester；4-brom-2-methylbut-2-enoate；4-bromo-2-methyl-2-butenoic acid methyl ester；Methyl 4-bromo-2-methylbut-2-enoate
• CAS: 99968-60-2
• 化学式: C₆H₉BrO₂
• 分子量: 193.04
• InChiKey: RYSPSQWXGPGQBI-UHFFFAOYSA-N

物化性质

• 沸点：
  86-90 °C(Press: 8 Torr)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  methyl 4-bromo-2-methyl-but-2-enoate 在 草酰氯 、 水 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (E)-4-(3-methoxyphenoxy)-2-methylbut-2-enoyl chloride
  参考文献：
  名称：

  通过还原性偶联，Nazarov环化序列从α，β-不饱和酰氯和炔烃聚合获得多环环戊烷类化合物

  摘要：

  α，β-不饱和酰氯A与炔基B的还原偶联提供了Nazarov环化前体α-羧基二乙烯基酮C的聚合通道。C的环化产生中间体羟基烯丙基阳离子中间体D，该中间体可被束缚的芳烃（Ar）捕集。所得产物可通过拴系的OH基团通过合适的离去基团X的亲核取代而进一步环化，以得到内酯（在随后的步骤中）。当X是合适的手性助剂（例如恶唑烷酮）时，该策略提供了获得同手性环戊烷的途径。

  DOI：

  10.1021/jo500040b
• 作为产物：
  描述：

  惕格酸 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 四氯化碳 为溶剂， 反应 44.0h， 生成 methyl 4-bromo-2-methyl-but-2-enoate
  参考文献：
  名称：

  Didehydrogeranylgeranyl (ΔΔGG):  A Fluorescent Probe for Protein Prenylation

  摘要：

  The first intrinsically fluorescent analog of geranylgeraniol, (2E,6E,8E,10E,12E,14E)-geranylgeraniol (all-trans-DeltaDeltaGGOH.1) has been synthesized stereoselectively and shown to substitute for the geranylgeranyl (GG) moiety in prenyl transferase reactions and in protein-ligand binding assays. All-trans-DeltaDeltaGGOH 1 showed blue fluorescence in methanol, with lambdaex = 310 nm and lambdaem = 410 nm (epsilon310 = 2.4 x 104 M-1 cm-1), but was only weakly fluorescent in aqueous solution. The prenyl transferase efficiency for DeltaDeltaGGPP 2 as a substrate for yeast protein geranylgeranyl transferase (PGGTase-I) was 60% relative to that for GGPP. The binding of DeltaDeltaGG-AcCysMe 3 to the recombinant Rho GTPase dissociation inhibitor (RhoGDI) had a KD of 15.1 +/- 1.2 muM, 6-fold lower than the affinity of GG-AcCysMe. Thus, the DeltaDeltaGG moiety is a novel fluorophore suitable for studying the interaction and subcellular localization of prenylated small GTPase proteins in signaling complexes.

  DOI：

  10.1021/ja0119144

文献信息

• BROMINATION OF ORGANIC ALLYLIC COMPOUNDS BY USING <i>N</i>,<i>N′</i>-DIBROMO-<i>N</i>,<i>N′-</i>1,2-ETHANE DIYL <i>BIS</i>(2,5-DIMETHYL BENZENE SULPHONYL)AMINE
  作者：Ardeshir Khazaei、Ramin Ghorbani Vaghei、Ebrahim Karkhanei

  DOI：10.1081/scc-120005417

  日期：2002.1.1

  ABSTRACT N,N′-Dibromo-N,N′-1,2-ethane diyl bis(2,5-dimethyl benzene sulphonyl)amine is an efficient brominating agent for bromination of allylic positions of different organic compounds. This reagent in presence of benzoyl peroxide can brominates the allylic positions of organic compounds in ambient conditions in carbon tetrachloride.

  摘要 N,N'-二溴-N,N'-1,2-乙烷二基双（2,5-二甲基苯磺酰基）胺是一种有效的溴化剂，用于溴化不同有机化合物的烯丙基位。该试剂在过氧化苯甲酰存在下可以在四氯化碳环境条件下溴化有机化合物的烯丙基位置。
• Total syntheses of smenothiazoles A and B
  作者：Xiao Ma、Yajie Chen、Sigui Chen、Zhengshuang Xu、Tao Ye

  DOI：10.1039/c7ob01818e

  日期：——

  Concise total syntheses of smenothiazoles A (1) and B (2), two distinguished vinyl chloride containing natural products isolated from the marine sponge S. aurea, have been developed. Silastannation, Stille reaction and a carefully controlled desilylchlorination were employed as key steps to construct unique polyketide acid fragments, and the optimized reaction conditions avoided migration of 2,5-diene

  简明的总合成smenothiazoles A（1）和B（2），即从海洋海绵金黄色葡萄球菌中分离得到的两种不同的含氯乙烯的天然产物。甲硅烷基化，斯蒂勒反应和精心控制的脱甲硅烷基氯反应被用作构建独特的聚酮酸片段的关键步骤，并且优化的反应条件避免了2,5-二烯向2,4-共轭体系的迁移。该报告明确证实了两种天然产物的结构。
• Copper-Catalyzed Asymmetric Kinugasa/Michael Addition Cascade Reactions for the Synthesis of Chiral Spiro β-Lactams
  作者：Yunlin Ao、Haowen Ma、Binghan Gan、Wenjing Wang、Jiehao Zhang、Wei Zhou、Xiaoqi Zhang、Qian Cai

  DOI：10.1021/acs.orglett.4c01568

  日期：2024.6.7

  A mild copper-catalyzed asymmetric Kinugasa/Michael addition cascade process is developed. The reaction of α, β-unsaturated ester-tethered propiolamides with nitrones provides an efficient protocol for the construction of functionalized chiral 2,6-diazaspiro[3.4]octane-1,5-dione products in satisfactory yields and with high enantio- and diastereoselectivities.

  开发了一种温和的铜催化不对称 Kinugasa/Michael 加成级联工艺。 α, β-不饱和酯系丙炔酰胺与硝酮的反应为构建官能化手性 2,6-二氮杂螺[3.4]辛烷-1,5-二酮产物提供了一种有效的方案，其收率令人满意，并且具有高对映体和非对映选择性。
• Synthesis of 1R-1H-Imidazo[1,2-a]pyridin-4-ium-8-olate Derivatives
  作者：Andriy V. Shelepyuk、Lyudmyla M. Potikha、Volodymyr O. Kovtunenko、Roman I. Zubatyuk、Oleg V. Shishkin

  DOI：10.1002/jhet.2094

  日期：2015.3

  A new method based on reaction of 4‐bromobut‐2‐enoates with N‐alkylimidazoles was proposed for obtaining 1R‐1H‐imidazo[1,2‐a]pyridin‐4‐ium‐8‐olate and 1‐R‐8‐methoxy‐1H‐imidazo[1,2‐a]pyridin‐4‐ium derivatives. The structures of synthesized compounds were confirmed by 1H, 13C NMR, elemental analysis, and X‐ray data.
• CN116082154
  申请人：——

  公开号：——

  公开（公告）日：——