m-tolyl 3-chloropropanoate | 158304-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: m-tolyl 3-chloropropanoate
• 英文别名: (3-Methylphenyl) 3-chloropropanoate
• CAS: 158304-80-4
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: PQGWOZPKEKYGPS-UHFFFAOYSA-N

物化性质

• 沸点：
  286.8±23.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  m-tolyl 3-chloropropanoate 在 aluminum (III) chloride 作用下， 反应 3.0h， 以30%的产率得到7-羟基-5-甲基-1-茚酮
  参考文献：
  名称：

  （S）-1-（6-（3-（（4-（1-（环丙烷羰基）哌啶-4-基）-2-甲基苯基）氨基）-2,3-二氢-1 H-茚满-的发现4-yl）pyridin-2-yl）-5-methyl-1 H-吡唑-4-羧酸，一种可溶性鸟苷酸环化酶激活剂，专门设计用于局部眼部递送以治疗青光眼

  摘要：

  可溶性鸟苷酸环化酶（sGC）是一氧化氮（NO）的内源性受体，与多种与氧化应激有关的疾病有关。在病理性氧化环境中，sGC的血红素基团可被氧化而变得对NO无响应，从而导致催化cGMP产生的能力下降。最近，功能异常的sGC / NO / cGMP途径与青光眼相关的眼内压升高有关。在这里，我们描述了专门设计用于局部眼部给药的分子的发现，该分子可以激活氧化的sGC，恢复催化cGMP产生的能力。这些努力最终导致了化合物（+）-23的鉴定，可在单次局部滴眼后24小时内强烈降低眼内压升高的食蟹猴模型中的眼内压，已被选择用于临床评估。

  DOI：

  10.1021/acs.jmedchem.8b00007
• 作为产物：
  描述：

  间甲酚 、 3-氯丙酰氯 以 苯 为溶剂， 反应 12.0h， 以95%的产率得到m-tolyl 3-chloropropanoate
  参考文献：
  名称：

  Synthesis of (.+-.)-Fredericamycin A

  摘要：

  The synthesis of (+/-)-fredericamycin A (1) is reported with full experimental detail. Preparations of building blocks for the upper (2) and lower (3) units of 1 are described. The union of 2 and 3 by a two-step 1,4-dipolar cycloaddition and the elaboration of the resulting product (19) into 1 are presented. The spiro 1,3-dione center in 1 was introduced utilizing a mild mercury-mediated pinacol rearrangement involving a 1,2-carbonyl migration. The reaction of benzylic cuprate anions ortho to aromatic esters has been shown to produce isochromarins in good yield. These isochromarins afford the biologically relevant isoquinolones upon treatment with ammonia.

  DOI：

  10.1021/ja00101a013

文献信息

• [EN] INDANE AND INDOLINE DERIVATIVES AND THE USE THEREOF AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS<br/>[FR] DÉRIVÉS D'INDANE ET D'INDOLINE ET LEUR UTILISATION EN TANT QU'ACTIVATEURS DE LA GUANYLATE CYCLASE SOLUBLE
  申请人：NOVARTIS AG

  公开号：WO2016001875A1

  公开（公告）日：2016-01-07

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了化合物(I)或其药学上可接受的盐；制造本发明化合物的方法及其治疗用途。本发明还提供了药理活性剂的组合和制药组合物。
• Rhodium(I)-Catalyzed Arylation of β-Chloro Ketones and Related Derivatives through Domino Dehydrochlorination/ Conjugate Addition
  作者：Quanbin Jiang、Tenglong Guo、Qingfu Wang、Ping Wu、Zhengkun Yu

  DOI：10.1002/adsc.201200821

  日期：2013.6.17

  Highly efficient arylations of β‐chloro ketones and their ester and amide derivatives were achieved by means of domino dehydrochlorination/Rh(I)‐catalyzed conjugate addition. In situ generated vinyl ketones and their analogues were identified as the reaction intermediates. The present synthetic protocol provides a concise route to (chiral) β‐aryl ketones, esters, and amides.

  β-氯酮及其酯和酰胺衍生物的高效芳基化是通过多米诺脱氢/ Rh（I）催化的共轭物加成反应实现的。原位生成的乙烯基酮及其类似物被鉴定为反应中间体。本合成方案为（手性）β-芳基酮，酯和酰胺提供了一条简明的途径。
• Copper-Catalyzed Tandem Asymmetric Borylation of β-Chloroalkyl Aryl Ketones and Related Compounds
  作者：Quanbin Jiang、Tenglong Guo、Zhengkun Yu

  DOI：10.1002/cctc.201402823

  日期：2015.2

  The Cu‐catalyzed, one‐pot tandem (asymmetric) borylation of β‐chloroalkyl aryl ketones via the in situ generated acyclic enones with bis(pinacolato)diboron was achieved efficiently to reach up to 97 % yield and 99 % enantioselectivity for the formal sp3 CCl borylation products. The present methodology provides an efficient alternative route to (chiral) alkylboron compounds.

  通过原位生成的无环烯酮与双（频哪醇）二硼烷进行Cu催化的一锅串联（不对称）β-氯烷基芳基酮的硼化反应，可以有效地实现形式sp的高达97％的收率和99％的对映选择性3种ç 氯硼基化产品。本方法为（手性）烷基硼化合物提供了有效的替代途径。
• Attempted novel preparation of dihydrocoumarin and coumarin; obtention of aryl acrylates and 3-chloropropionates
  作者：Jaswant R. Mahajan、Hugo C. Araújo

  DOI：10.1139/v87-035

  日期：1987.1.1

  It has been found that, contrary to the published report, there is no noticeable reaction between phenol and methyl acrylate in the presence of aluminum chloride to produce phenyl acrylate (1) and dihydrocoumarin (2). Although products having the reported spectral data can be obtained by the reaction of phenol with acrylyl chloride, these products are actually phenyl acrylate and phenyl 3-chloropropionate (4), there being detected no dihydrocoumarin. This reaction has now been extended to several substituted phenols and some naphthols. Attempts at cyclization of phenyl acrylate, phenyl 3-chloropropionate, or their mixtures have been unsuccessful.

  研究发现，与已发表的报告相反，苯酚和甲基丙烯酸酯在氯化铝存在下没有明显的反应，不能产生苯基丙烯酸酯（1）和二氢香豆素（2）。虽然通过苯酚与丙烯酰氯反应可以得到具有已报告光谱数据的产物，但事实上这些产物是苯基丙烯酸酯和苯基3-氯丙酸酯（4），没有检测到二氢香豆素。这个反应现已扩展到几种取代苯酚和一些萘酚。尝试将苯基丙烯酸酯、苯基3-氯丙酸酯或它们的混合物环化均未成功。
• Indane and indoline derivatives and the use thereof as soluble guanylate cyclase activators
  申请人：Adams Christopher M.

  公开号：US10208018B2

  公开（公告）日：2019-02-19

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种式（I）化合物或其药学上可接受的盐；一种制造本发明化合物的方法及其治疗用途。本发明进一步提供了一种药理活性剂的组合物和一种药物组合物。