3-(2-iodo-5-methoxyphenyl)propanoic acid | 99254-50-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(2-iodo-5-methoxyphenyl)propanoic acid
• 英文别名: 2-Iodo-5-methoxybenzenepropanoic acid
• CAS: 99254-50-9
• 化学式: C₁₀H₁₁IO₃
• 分子量: 306.1
• InChiKey: BMIFCJUUATYOHS-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))
• 沸点：
  391.5±32.0 °C(Predicted)
• 密度：
  1.705±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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-iodo-5-methoxyphenyl)propanoic acid 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 N-<2-(3,4-dimethoxyphenyl)ethyl>-2-iodo-5-methoxy-N-methylbenzenepropanamide
  参考文献：
  名称：

  2-Ethynylbenzenealkanamines. A new class of calcium entry blockers

  摘要：

  A series of 2-(aryl- or alkylethynyl)benzenealkanamines were synthesized. They exhibit antihypertensive activity in spontaneously hypertensive rats and coronary vasodilator activity with minimal negative inotropic activity in the "Langendorff" guinea pig heart in vitro. They have been shown to exert their activity by inhibition of Ca2+ influx across cell membranes. Optimal activity is found among the N-(arylethyl)-5-methoxy-alpha-methyl-2-(phenylethynyl)ben zeneethanamines and -propanamines.

  DOI：

  10.1021/jm00398a023
• 作为产物：
  描述：

  (2-碘-5-甲氧基苯基)甲醇 在 重铬酸吡啶 、 甲酸 、 silica gel 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-(2-iodo-5-methoxyphenyl)propanoic acid
  参考文献：
  名称：

  Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C–N Bond Formation

  摘要：

  A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and, are present in bioactive, molecules. This work highlights the challenge Of competing intra-vs intermolecular palladium-catalyzed processes.

  DOI：

  10.1021/acs.orglett.7b03577

文献信息

• Synthesis of <i>N</i>-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars
  作者：Boris Letribot、Wafa Redjdal、Belkacem Benmerad、Franck Le Bideau、Mouâd Alami、Samir Messaoudi

  DOI：10.1021/acs.orglett.0c01262

  日期：2020.6.5

  An efficient intramolecular Pd-catalyzed N-arylation of o-iodo-amidosugars for the synthesis of N-glycosylated oxindoles has been reported. The coupling reaction takes place in toluene and involves Pd(OAc)2/RuPhos catalytic systems in the presence of K2CO3. This versatile approach was extended successfully to the synthesis of other N-glycosylated heterocycles.

  已经报道了用于合成N-糖基化的羟吲哚的有效的分子内Pd催化的O-碘-氨基糖的N-芳基化。偶联反应在甲苯中进行，并且涉及在K 2 CO 3存在下的Pd（OAc）2 / RuPhos催化体系。这种通用方法已成功扩展到其他N-糖基化杂环的合成。
• Aralykyl (arylethynyl)aralkyl amines and their use as vasodilators and
  申请人：McNeilab, Inc.

  公开号：US04661635A1

  公开（公告）日：1987-04-28

  Acetylenes of the formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2 q, Alk, R.sup.3, n and R.sup.4 are as defined herein and Ar.sup.1 and Ar.sup.2 are aromatic, including the salts and ammonium derivatives of formula (I), in treating angina, hypertension and cardiac arrhythmias. Pharmaceutical compositions, methods of use and synthesis and novel intermediates are also part of the invention.

  公式（I）的乙炔化合物：##STR1## 其中Y，m，R.sup.1，R.sup.2，q，Alk，R.sup.3，n和R.sup.4如本文所定义，Ar.sup.1和Ar.sup.2是芳香族，包括公式（I）的盐和铵衍生物，在治疗心绞痛、高血压和心律不齐方面具有作用。药物组合物、使用方法、合成方法和新颖中间体也是该发明的一部分。
• Acetylene amines and their use as vasodilators and antihypertensives
  申请人：McNeilab, Inc.

  公开号：US04725602A1

  公开（公告）日：1988-02-16

  Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.

  以下式(I)的乙炔化合物：##STR1## 其中Y、m、R.sup.1、R.sup.2、R.sup.3、n和R.sup.4的定义见下文，R.sup.5是氢、烷基、环烷基或取代烷基，是有用的血管扩张剂和降压药物。
• Methods for the treatment of hypertension
  申请人：McNeilab, Inc.

  公开号：US04898889A1

  公开（公告）日：1990-02-06

  Acetylene compounds of the formula (I): ##STR1## wherein Y, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as described herein, m is 0-3, n is 0-2 and Ar is phenyl or an aromatic heterocycle are disclosed. The compounds possess antihypertensive and anti-anginal properties and may be used in the treatment of humans. Methods for the preparation and use of such acetylene compounds are also disclosed.

  公开了化学式（I）的乙炔化合物：##STR1##其中Y、R.sub.1、R.sub.2、R.sub.3和R.sub.4如本文所述，m为0-3，n为0-2，Ar为苯或芳香杂环。这些化合物具有降压和抗心绞痛的特性，可用于人类的治疗。还公开了制备和使用这种乙炔化合物的方法。
• Acetylene derivatives for the treatment of hypertension and angina
  申请人：McNeilab, Inc.

  公开号：EP0145361A2

  公开（公告）日：1985-06-19

  57 Acetylene compounds of the formula (I): wherein Y, R1, R,, R3, and R4 are as described herein, m is 0-3, n is 0-2 and Ar is pehnyl or an aromatic heterocycle are disclosed. The compounds possess antihypertensive and anti-anginal properties and may be used in the treatment of humans. Methods for the preparation and use of such acetylene compounds are also disclosed.

  57 本发明公开了式 (I) 的乙炔化合物：其中 Y、R1、R、R3 和 R4 如本文所述，m 为 0-3，n 为 0-2，Ar 为正烷基或芳香杂环。 这些化合物具有抗高血压和抗心绞痛的特性，可用于人类治疗。 本发明还公开了制备和使用此类乙炔化合物的方法。