(Z)-3-bromoacrylaldehyde | 117291-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-bromoacrylaldehyde
• 英文别名: (Z)-bromoacrolein；3-Brom-propenal；(Z)-3-bromoprop-2-enal
• CAS: 117291-85-7
• 化学式: C₃H₃BrO
• 分子量: 134.96
• InChiKey: DYKZSUCEYQFDRC-UPHRSURJSA-N

物化性质

• 沸点：
  149.2±23.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-bromoacrylaldehyde 、 (1R,2S,4R,5R,8R,9S,11R)-9-formyl-5-methyl-2-[[(2R,5R)-5-methylmorpholin-2-yl]oxymethyl]-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid 在 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties

  摘要：

  The synthesis and antifungal activity of 5- and 5'-6'-substituted azasordarin derivatives are described. Modification of the 5'-position led to the discovery of the spirocyclopentyl analogue 7g, which is the first azasordarin to register single-digit MIC values versus Aspergillus spp. Further investigation identified the 5'-i-Pr derivative 7b, which displays superior pharmacokinetic properties compared to other azasordarins. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00161-6
• 作为产物：
  描述：

  顺-3-溴丙烯酸乙酯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-3-bromoacrylaldehyde
  参考文献：
  名称：

  Synthesis of the C1−C13 Tetraenoate Subunit of the Chivosazoles

  摘要：

  Using a combination of asymmetric vinylogous Mukaiyama aldol and Stifle cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated (2E,4Z,6E,8Z)-tetraenoate motif and anti-configured C10 and C11 stereocenters of the chivosazoles, terminates in a (Z)-vinyl bromide for the planned cross-coupling to a northern hemisphere fragment.

  DOI：

  10.1021/ol101630p

文献信息

• Identification of a broad-Spectrum azasordarin with improved pharmacokinetic properties
  作者：Michael H. Serrano-Wu、Denis R.St. Laurent、Tina M. Carroll、Marco Dodier、Qi Gao、Patrice Gill、Claude Quesnelle、Anne Marinier、Charles E. Mazzucco、Alicia Regueiro-Ren、Terry M. Stickle、Dedong Wu、Hyekyung Yang、Zheng Yang、Ming Zheng、Mary E. Zoeckler、Dolatrai M. Vyas、Balu N. Balasubramanian

  DOI：10.1016/s0960-894x(03)00161-6

  日期：2003.4

  The synthesis and antifungal activity of 5- and 5'-6'-substituted azasordarin derivatives are described. Modification of the 5'-position led to the discovery of the spirocyclopentyl analogue 7g, which is the first azasordarin to register single-digit MIC values versus Aspergillus spp. Further investigation identified the 5'-i-Pr derivative 7b, which displays superior pharmacokinetic properties compared to other azasordarins. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of the C1−C13 Tetraenoate Subunit of the Chivosazoles
  作者：Ian Paterson、S. B. Jennifer Kan、Lisa J. Gibson

  DOI：10.1021/ol101630p

  日期：2010.8.20

  Using a combination of asymmetric vinylogous Mukaiyama aldol and Stifle cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated (2E,4Z,6E,8Z)-tetraenoate motif and anti-configured C10 and C11 stereocenters of the chivosazoles, terminates in a (Z)-vinyl bromide for the planned cross-coupling to a northern hemisphere fragment.