5-(2-propenyl)-2,3-dimethoxybenzoic acid | 263250-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-propenyl)-2,3-dimethoxybenzoic acid
• 英文别名: 5-Allyl-2,3-dimethoxybenzoic acid；2,3-dimethoxy-5-prop-2-enylbenzoic acid
• CAS: 263250-30-2
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: LDYILRISBAHEOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-propenyl)-2,3-dimethoxybenzoic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 5-(2-propenyl)-2,3-dimethoxybenzoyl chloride
  参考文献：
  名称：

  Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues

  摘要：

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.

  DOI：

  10.1016/s0223-5234(97)81676-5
• 作为产物：
  描述：

  2,3-dimethoxy-5-(2-propenyl)benzoic acid, methyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以81%的产率得到5-(2-propenyl)-2,3-dimethoxybenzoic acid
  参考文献：
  名称：

  Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues

  摘要：

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.

  DOI：

  10.1016/s0223-5234(97)81676-5

文献信息

• Iron-catalyzed oxidative C–C(vinyl) σ-bond cleavage of allylarenes to aryl aldehydes at room temperature with ambient air
  作者：Binbin Liu、Lu Cheng、Penghui Hu、Fangning Xu、Dan Li、Wei-Jin Gu、Wei Han

  DOI：10.1039/c9cc01995b

  日期：——

  heteroatoms to give aryl aldehydes is reported. The unstrained carbon–carbon single bond cleavage reaction uses ambient air as the sole oxidant, proceeds efficiently at room temperature, and allows for exceptional functional-group tolerance, which addresses the long-standing challenges of current C–C bond cleavage/functionalization. Notably, the method enables rapid late-stage oxidation of complex bioactive

  据报道，在没有杂原子的帮助下，烯丙基芳烃的一般和选择性铁催化烯丙基的C–C（乙烯基）σ键裂解可得到芳基醛。无应变的碳-碳单键裂解反应使用环境空气作为唯一氧化剂，在室温下有效进行，并具有出色的官能团耐受性，从而解决了当前C-C键裂解/官能化的长期挑战。值得注意的是，该方法能够使复杂的生物活性分子快速后期氧化，并可用于加速从容易获得的化学原料中合成天然产物（香兰素和葡糖香兰素）。
• ENTEROBACTIN CONJUGATES AND USES THEREOF
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：US20150105337A1

  公开（公告）日：2015-04-16

  The present invention provides novel enterobactin-cargo conjugates, such as compounds of Formula (I), and salts thereof, where X is the cargo and may be an antibiotic, a fluorophore, or biotin. The present invention also provides complexes, compositions, kits, and methods that involve the compounds of Formula (I) and are useful in delivering a cargo to a bacterium, treating a bacterial infection, cystic fibrosis, and/or inflammatory bowel disease in a subject, preventing a bacterial infection, cystic fibrosis, and/or inflammatory bowel disease in a subject, inhibiting the growth of or killing a bacterium, or determining the concentration of a bacterium in a biological sample. In certain embodiments, the bacterium is a Gram-negative bacterium.

  本发明提供了新型肠杆菌铁胞内载体共轭物，如式(I)化合物及其盐，其中X是载体，可以是抗生素、荧光素或生物素。本发明还提供了涉及式(I)化合物的络合物、组合物、试剂盒和方法，用于将载体传递给细菌，治疗受试者的细菌感染、囊性纤维化和/或炎症性肠病，预防受试者的细菌感染、囊性纤维化和/或炎症性肠病，抑制或杀死细菌的生长，或确定生物样品中细菌的浓度。在某些实施例中，细菌是革兰氏阴性细菌。
• PROCESS FOR PREPARING SYNTHETIC PARA-EUGENOL
  申请人：SABIC Global Technologies B.V.

  公开号：EP3027585A2

  公开（公告）日：2016-06-08
• US4036772A
  申请人：——

  公开号：US4036772A

  公开（公告）日：1977-07-19
• US9902986B2
  申请人：——

  公开号：US9902986B2

  公开（公告）日：2018-02-27