3-异丙氧基-4-甲氧基苯硼酸 | 516465-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-异丙氧基-4-甲氧基苯硼酸
• 英文名称: 3-isopropoxy-4-methoxyphenylboronic acid
• 英文别名: (4-methoxy-3-propan-2-yloxyphenyl)boronic acid
• CAS: 516465-82-0
• 化学式: C₁₀H₁₅BO₄
• 分子量: 210.038
• InChiKey: DMDYJEGUJMIPEX-UHFFFAOYSA-N

物化性质

• 熔点：
  115-135 °C
• 沸点：
  352.7±52.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 3-Isopropoxy-4-methoxyphenylboronic acid
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-Isopropoxy-4-methoxyphenylboronic acid
CAS number: 516465-82-0

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H15BO4
Molecular weight: 210.0

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-异丙氧基-4-甲氧基苯硼酸 在 1,1'-双(二苯基膦)二茂铁 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 sodium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.75h， 生成 3,11-diisopropoxy-14-(3-isopropoxy-4-methoxyphenyl)-2,12-dimethoxy-9-(phenylsulfanyl)-8,9-dihydro-6H-[1]-benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin-6-one
  参考文献：
  名称：

  Modular Synthesis of Lamellarins via Regioselective Assembly of 3,4,5-Differentially Arylated Pyrrole-2-carboxylates

  摘要：

  A modular synthesis of lamellarins via 3,4,5-differentially arylated pyrrole-2-carboxylate intermediates has been developed. The key reactions employed are Br-Li exchange-methoxycarbonylation of 2,5-dibromo-1-(tert-butoxycarbonyl)-1H-pyrrole (1) followed by palladium-catalyzed iterative Suzuki-Miyaura coupling of the pyrrole core. The 3,4,5-triarylpyrrole 4 thus synthesized was readily converted to 5,6-saturated lamellarin L (2) and 5,6-unsaturated lamellarin N (3) via lactonization followed by annulation of the pyrrole nitrogen and lateral aromatic ring at C5 using 2-bromoethyl phenyl sulfide or bromoacetaldehyde dimethyl acetal as two-carbon homologation agents. In principle, this strategy allows the production of diverse lamellarins in short steps with high yields using readily accessible arylboronic acids as aromatic modules.

  DOI：

  10.1021/jo402181w
• 作为产物：
  描述：

  2,4-二溴苯甲醚 在 正丁基锂 、 叔丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二甲基亚砜 、 正戊烷 为溶剂， 反应 20.0h， 生成 3-异丙氧基-4-甲氧基苯硼酸
  参考文献：
  名称：

  薄片蛋白D，L和N的全合成

  摘要：

  通过使用Hinsberg型吡咯合成法和钯催化的3,4-二羟基吡咯二酚6的Suzuki-Miyaura偶联，已经完成了细胞毒性海洋生物碱，薄片蛋白D，L和N的总合成。普通中间体6的层状蛋白D，L和N的总产率分别为54％，58％和50％。

  DOI：

  10.1016/j.tet.2005.10.014

文献信息

• [EN] ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014135495A1

  公开（公告）日：2014-09-12

  The present invention discloses compounds of Formula I: wherein the variables in Formula I are defined as described herein. Also disclosed are pharmaceutical compositions containing such compounds and methods for using the compounds of Formula I in the prevention or treatment of HCV infection.

  本发明公开了化合物的结构式I：其中结构式I中的变量如本文所述。还公开了含有这些化合物的药物组合物，以及使用结构式I中的化合物预防或治疗HCV感染的方法。
• Highly Efficient Gold-Catalyzed Synthesis of Dibenzocycloheptatrienes
  作者：Daniel Pflästerer、Eva Rettenmeier、Severin Schneider、Edgar de Las Heras Ruiz、Matthias Rudolph、A. Stephen K. Hashmi

  DOI：10.1002/chem.201402015

  日期：2014.5.26

  Dibenzocycloheptatrienes are obtained by a gold‐catalyzed 7‐exo‐dig hydroarylation protocol in a highly efficient manner. The gold‐catalyzed reaction usually gives the products in high yields and excellent selectivity. This procedure provides an easy and efficient access to dibenzocycloheptanoids, which are an interesting and unique class of natural products. This was underlined by the first total

  二苯并环庚烯是通过金催化的7 - exo - dig芳构化方法高效获得的。金催化的反应通常以高收率和优异的选择性提供产物。该程序可轻松有效地获得二苯并环庚烷类化合物，这是一类有趣且独特的天然产物。首次完全合成网状酚强调了这一点。
• [EN] INDOLE-CONTAINING COMPOUNDS WITH ANTI-TUBULIN AND VASCULAR TARGETING ACTIVITY<br/>[FR] COMPOSES CONTENANT DE L'INDOLE A ACTIVITE ANTI-TUBULINE ET DE CIBLAGE VASCULAIRE
  申请人：UNIV BAYLOR

  公开号：WO2004099139A1

  公开（公告）日：2004-11-18

  Trimethoxyphenyl substituted indole ligands have been discovered which demonstrate impressive cytotoxicity as well as a remarkable ability to inhibit tubulin assembly. Such compounds as well as related derivatives are excellent clinical candidates for the treatment of cancer in humans. In addition, certain of these ligands, as pro-drugs, may well prove to be tumor selective vascular targeting chemotherapeutic agents or to have vascular targeting activity resulting in the selective prevention and/or destruction of nonmalignant proliferating vasculature.

  已发现了取代三甲氧基苯基吲哚配体，这些配体表现出令人印象深刻的细胞毒性，以及抑制微管组装的显著能力。这类化合物以及相关衍生物是治疗人类癌症的优秀临床候选药物。此外，这些配体中的某些作为前药，很可能被证明是肿瘤选择性血管靶向化疗药物，或具有靶向血管活性，从而选择性地预防和/或破坏非恶性增殖的血管系统。
• Synthesis of Lamellarins via Regioselective Assembly of 1,2-Diarylated [1]Benzopyrano[3,4-b]pyrrol-4(3H)-one Core
  作者：Tsutomu Fukuda、Takatoshi Katae、Issei Harada、Masatomo Iwao

  DOI：10.3987/com-16-s(s)63

  日期：——

  A modular synthesis of lamellarins has been developed. The key reactions in this synthesis are the assembly of 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-ones from a preexisting [1]benzopyrano[3,4-b]pyrrol4(3H)-one core and the appropriate arylboronic acids. The obtained 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-ones could be easily converted into the corresponding lamellarin derivatives

  已经开发了层状蛋白的模块化合成。该合成中的关键反应是由预先存在的[1]苯并吡喃[3,4-b]吡咯4( 3H)-一个核心和适当的芳基硼酸。得到的1,2-二芳基[1]苯并吡喃[3,4-b]pyrrol-4(3H)-ones可以通过吡咯氮和C2芳环之间的分子内环化很容易地转化为相应的层状结构衍生物。引言 层层素是一种多环吡咯生物碱，具有独特的 14-苯基-6H-[1]苯并吡喃[4́,3́:4,5]吡咯并[2,1-a]异喹啉-6-环系统。在极少数情况下（层状蛋白 O、P、Q 和 R），这些化合物具有简单的非稠合 3,4-diarylpyrrole-2-carboxylate 结构。自从第一次从海洋前支软体动物 Lamellaria sp. 中分离出层状蛋白 A-D。1985 年，从被囊类动物、海绵类和前枝类动物中分离出 50 多种层状蛋白。这些层状蛋白表现出广泛的有用生物活性：针对几种癌细胞系的有效抗增殖活性、多药耐药性
• Regioselective Synthesis of 2,4-Differentially Arylated Pyrroles and Its Application to The Synthesis of Lamellarins
  作者：Masatomo Iwao、Tsutomu Fukuda、Mizuho Anzai

  DOI：10.3987/com-15-s(t)49

  日期：——

  been developed. In the last decade, several strategies for the synthesis of 2,4-differentially arylated pyrroles have been reported. They involve the interesting key reactions such as ring formation from 1,3-diaryl-4-nitrobutan-1-ones, carbanion induced pyrrole synthesis from azirines and ketones, ozonolysis of homoallylic ketones followed by Paal–Knorr condensation, gold-catalyzed reaction with N-tosyl

  通过逐步钯催化的 Suzuki-Miyaura 偶联 N-苯磺酰基-4-溴-2-碘吡咯与不同的芳基硼酸，开发了一种合成 2,4-差异芳基化吡咯的有效方法。该方法已应用于海洋天然产物板层素的新合成。引言 吡咯衍生物广泛存在于具有广泛生物活性的天然产物中。它们也嵌入在一些药剂中。此外，它们还被用作制备具有独特电子和光物理特性的功能材料的宝贵组成部分。因此，已经开发了多种用于从头构建环和对吡咯核进行区域选择性功能化的合成方法。在过去的十年里，已经报道了几种合成 2,4-差异芳基化吡咯的策略。它们涉及有趣的关键反应，例如 1,3-diaryl-4-nitrobutan-1-ones 的成环反应、碳负离子诱导的氮杂环丙烷和酮合成吡咯、高烯丙基酮的臭氧分解以及 Paal-Knorr 缩合、金催化反应N-甲苯磺酰基炔基氮丙啶，铑催化的 N-甲苯磺酰基-1,2,3-三唑与末端炔烃或烯基烷基醚的环化反应，铜