5-chloro-2-nitrocinnamaldehyde | 193140-32-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 5-chloro-2-nitrocinnamaldehyde
• 英文别名: 3-(5-chloro-2-nitrophenyl)prop-2-enal
• CAS: 193140-32-8
• 化学式: C₉H₆ClNO₃
• 分子量: 211.605
• InChiKey: IVCVRROMYAESDS-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  383.5±37.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-2-nitrocinnamaldehyde 在 4-二甲氨基吡啶 、 溴 、 C₃₆H₄₈N₃O⁽¹⁺⁾*Cl^(1-) 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 25.5h， 生成 4-methoxyphenyl (S)-3-(5-chloro-2-nitrophenyl)-3-(diphenylphosphorothioyl)propanoate
  参考文献：
  名称：

  Carbene‐Catalyzed Enantioselective Hydrophosphination of α‐Bromoenals to Prepare Phosphine‐Containing Chiral Molecules

  摘要：

  AbstractDisclosed herein is the first carbene‐organocatalyzed asymmetric addition of phosphine nucleophiles to the in situ generated α,β‐unsaturated acyl azolium intermediates. Our reaction enantioselectively constructs carbon–phosphine bonds and prepares chiral phosphines with high optical purities. The phosphine products are suitable for transforming to chiral ligands or catalysts with applications in asymmetric catalysis. The diarylalkyl or trialkyl phosphine products from our catalytic reactions, air‐sensitive and reactive in nature, can be trapped (and stored) in their sulfur‐oxidized form for operational simplicities.

  DOI：

  10.1002/anie.202112860
• 作为产物：
  描述：

  5-氯-2-硝基苯甲醛 、 甲酰甲撑基三苯基磷 以 二氯甲烷 为溶剂， 以84%的产率得到5-chloro-2-nitrocinnamaldehyde
  参考文献：
  名称：

  Phenylpyrrole derivatives as neural and inducible nitric oxide synthase (nNOS and iNOS) inhibitors

  摘要：

  We have previously described a series of 3-phenyl-4,5-dihydro-1H-pyrazole derivatives as moderately potent nNOS inhibitors. As a follow up of these studies, several new 5-phenyl-1H-pyrrole-2-carboxamide derivatives have been synthesized, and their biological evaluation as in vitro inhibitors of both neural and inducible Nitric Oxide Synthase (nNOS and iNOS) is described. Some of these compounds show good iNOS/nNOS selectivity and the more potent compounds 5-(2-aminophenyl)-1H-pyrrole-2-carboxilic acid methylamide (QFF205) and cyclopentylamide (QFF212) have been tested as regulators of the in vivo nNOS and iNOS activity. Both compounds prevented the increment of the inducible NOS activity in both cytosol (iNOS) and mitochondria (i-mtNOS) observed in the MPTP model of Parkinson's disease. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.013

文献信息

• Domino C−S/C−N Bond Formation Using Well‐Defined Copper‐Phosphine Complex Catalyst: Divergent Approach to 3‐Sulfenylated Indoles
  作者：Ramuel John Inductivo Tamargo、Sung Hong Kim、Yong Rok Lee

  DOI：10.1002/adsc.201900612

  日期：2019.9.3

  3‐thioindoles in good‐to‐excellent yields involving sulfenylation between 2‐nitrocinnamaldehydes and various thiols using a well‐defined copper(I)‐phosphine complex catalyst. This unconventional divergent approach involves in situ generation of indoles via domino C−S/C−N bond formation initiated by sulfa‐Michael addition followed by intramolecular N‐heteroannulation. This protocol shows good chemoselectivity

  开发了一种协议，用于使用定义明确的铜（I）-膦络合物催化剂以良好的优异产率合成3-硫代吲哚，涉及2-硝基肉桂醛和各种硫醇之间的亚磺酰基化。这种非常规的发散方法涉及通过磺胺-迈克尔加成反应引发的多米诺骨牌CS / C-N键形成原位生成吲哚，然后分子内进行N-异环化。该方案显示出良好的化学选择性和广泛的底物范围。为简要说明该方法的价值，由市售的2-硝基查尔酮和硫醇制备了2-苯甲酰基-3-亚磺酰化的吲哚。