(2,2-dimethylbenzo[1,3]dioxol-5-yl)boronic acid | 227306-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (2,2-dimethylbenzo[1,3]dioxol-5-yl)boronic acid
• 英文别名: 2,2-dimethyl-1,3-benzodioxol-5-ylboronic acid；(2,2-dimethylbenzo[d][1,3]dioxolane-5-yl)boronic acid；(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)boronic acid；(2,2-Dimethyl-1,3-benzodioxol-5-yl)boronic acid
• CAS: 227306-23-2
• 化学式: C₉H₁₁BO₄
• 分子量: 193.995
• InChiKey: RVNFQXCMRDUEBI-UHFFFAOYSA-N

物化性质

• 熔点：
  187-189 °C
• 沸点：
  332.8±52.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,2-dimethylbenzo[1,3]dioxol-5-yl)boronic acid 在 四(三苯基膦)钯 、 samarium diiodide 、 sodium carbonate 、 lithium chloride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (1R)-2β-carbomethoxy-3β-(2,2-dimethylbenzo[1,3]dioxol-5-yl)tropane
  参考文献：
  名称：

  Synthesis and biological activity of 2-Carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes

  摘要：

  Cocaine inhibits the dopamine transporter and the consequent elevation of dopamine is thought to contribute to the addictive properties of cocaine. Tropane analogues of cocaine, targeted to the dopamine transporter (DAT), are a significant focus of drug design for cocaine addiction medications. Herein, we report the function of the ortho hydroxy substituents in dopamine with respect to the azabicyclo[3.2.1]octane skeleton. The introduction of the o-dihydroxyl functionality led to reduced binding potency at monoamine transporters, rather than enhanced interaction with the DAT. It is therefore likely that the binding site for these compounds on the DAT is not the same as that for dopamine. Notwithstanding the moderate potency of the free catechols (> 100 nM), 7 manifested stimulant activity with a duration of effect that exceeded 4 h in a rat locomotor activity assay. Compound 10, a diacetoxy prodrug for 7, substituted fully for cocaine in a rat drug-discrimination paradigm and is now undergoing further investigation as a potential medication for cocaine abuse. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.014
• 作为产物：
  描述：

  2,2-二甲基-1,3-苯并二恶茂烷 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (2,2-dimethylbenzo[1,3]dioxol-5-yl)boronic acid
  参考文献：
  名称：

  [EN] PYRIDAZINONE COMPOUND, PREPARATION METHOD, HERBICIDE COMPOSITION AND USE THEREOF
  [FR] COMPOSÉ DE PYRIDAZINONE, PROCÉDÉ DE PRÉPARATION, COMPOSITION HERBICIDE ET UTILISATION ASSOCIÉE
  [ZH] 一种哒嗪酮类化合物、制备方法、除草剂组合物及用途

  摘要：

  一种哒嗪酮类化合物、制备方法、除草剂组合物及用途，具体涉及一种通式I所示的哒嗪酮类化合物或其农业上可接受的盐；以式II、式III化合物或式IV、式III化合物为原料制备式I化合物的方法；含有式I化合物或其农业上可接受盐的除草剂组合物及在控制杂草上的用途。该除草剂的施用范围广泛、安全性好且选择性高，能在有效抑制杂草的同时，几乎不损害正常作物；并且该除草剂的制备方法操作简单、成本低廉，适合大规模的工业化生产。

  公开号：

  WO2023040686A1

文献信息

• [EN] PYRIDAZINONE COMPOUND, PREPARATION METHOD, HERBICIDE COMPOSITION AND USE THEREOF<br/>[FR] COMPOSÉ DE PYRIDAZINONE, PROCÉDÉ DE PRÉPARATION, COMPOSITION HERBICIDE ET UTILISATION ASSOCIÉE<br/>[ZH] 一种哒嗪酮类化合物、制备方法、除草剂组合物及用途
  申请人：[en]JIANGSU FLAG CHEMICAL INDUSTRY CO., LTD.;[zh]江苏中旗科技股份有限公司

  公开号：WO2023040686A1

  公开（公告）日：2023-03-23

  一种哒嗪酮类化合物、制备方法、除草剂组合物及用途，具体涉及一种通式I所示的哒嗪酮类化合物或其农业上可接受的盐；以式II、式III化合物或式IV、式III化合物为原料制备式I化合物的方法；含有式I化合物或其农业上可接受盐的除草剂组合物及在控制杂草上的用途。该除草剂的施用范围广泛、安全性好且选择性高，能在有效抑制杂草的同时，几乎不损害正常作物；并且该除草剂的制备方法操作简单、成本低廉，适合大规模的工业化生产。
• US6387931
  申请人：——

  公开号：——

  公开（公告）日：——
• BENZIMIDAZOLE DERIVATIVES AS GPX4 INHIBITORS
  申请人：[en]SONATA THERAPEUTICS, INC.

  公开号：WO2024129780A1

  公开（公告）日：2024-06-20

  The present disclosure provides a compounds of Formula (I) or a pharmaceutically acceptable salt thereof and its use in,e.g. treating a condition, disease, or disorder in which inhibiting GPX4 in a subject is of therapeutic benefit, specifically in treating cancer or autoimmune diseases. This disclosure also features a composition containing the same as well as methods of using and making the same.
• Synthesis and biological activity of 2-Carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes
  作者：Peter C Meltzer、Mark McPhee、Bertha K Madras

  DOI：10.1016/j.bmcl.2003.07.014

  日期：2003.11

  Cocaine inhibits the dopamine transporter and the consequent elevation of dopamine is thought to contribute to the addictive properties of cocaine. Tropane analogues of cocaine, targeted to the dopamine transporter (DAT), are a significant focus of drug design for cocaine addiction medications. Herein, we report the function of the ortho hydroxy substituents in dopamine with respect to the azabicyclo[3.2.1]octane skeleton. The introduction of the o-dihydroxyl functionality led to reduced binding potency at monoamine transporters, rather than enhanced interaction with the DAT. It is therefore likely that the binding site for these compounds on the DAT is not the same as that for dopamine. Notwithstanding the moderate potency of the free catechols (> 100 nM), 7 manifested stimulant activity with a duration of effect that exceeded 4 h in a rat locomotor activity assay. Compound 10, a diacetoxy prodrug for 7, substituted fully for cocaine in a rat drug-discrimination paradigm and is now undergoing further investigation as a potential medication for cocaine abuse. (C) 2003 Elsevier Ltd. All rights reserved.
• Rotational Energy Barrier around the C1–C11 Single Bond in Lamellarins: A Study by Variable-Temperature NMR
  作者：Masatomo Iwao、Tsutomu Fukuda、Ryosuke Itoyama、Terufusa Minagawa

  DOI：10.3987/com-13-s(s)69

  日期：——

  In order to estimate the free energy barrier to rotation around the C1-C11 single bond in lamellarins, new lamellarin analogues (1a), (1b), (2a), and (2b) possessing diastereotopic protons or carbons at the C1 aryl moiety were synthesized. Variable-temperature H-1 and C-13 NMR measurements of these analogues revealed that the free energy barriers to rotation around the C1-C11 axis in 5,6-saturated and 5,6-unsaturated lamellarins were around 72-74 and 83-87 kJ/mol, respectively.