吲哚-5-硼酸频那醇酯 | 937366-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 吲哚-5-硼酸频那醇酯
• 中文别名: 吲哚-3-硼酸频哪酯；吲哚-5-硼酸嚬哪醇酯
• 英文名称: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS: 937366-54-6
• 化学式: C₁₄H₁₈BNO₂
• 分子量: 243.113
• InChiKey: WQPRSRMWYVTUTE-UHFFFAOYSA-N

物化性质

• 沸点：
  396.0±15.0 °C(Predicted)
• 密度：
  1.11

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Indole-3-boronic acid pinacol ester
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Indole-3-boronic acid pinacol ester
CAS number: 937366-54-6

---

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, under −20◦C.
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: C14H18BNO2
Molecular weight: 243.1

---

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

---

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：

  吲哚-5-硼酸频那醇酯 在 四(三苯基膦)钯 作用下， 以 乙二醇二甲醚 、 乙二醇甲醚 为溶剂， 生成 5-chloro-N-(4-(2-(dimethylamino)ethyl)phenyl)-4-(1H-indol-3-yl)pyrimidin-2-amine
  参考文献：
  名称：

  Synthesis and biological study of 2-amino-4-aryl-5-chloropyrimidine analogues as inhibitors of VEGFR-2 and cyclin dependent kinase 1 (CDK1)

  摘要：

  The series of 2-amiiio-4-aryl-5-chloropyrimidines was discovered to be potent for both VEGFR-2 and CDK1. Described here are the chemistry for analogue synthesis, SAR study, and its kinase selectivity prolifing. The full rat PK data and in vivo efficacy study are also included. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.086
• 作为产物：
  描述：

  1-叔丁氧羰基-吲哚-3-硼酸,频哪醇酯 反应 0.75h， 以64%的产率得到吲哚-5-硼酸频那醇酯
  参考文献：
  名称：

  Boc Groups as Protectors and Directors for Ir-Catalyzed C−H Borylation of Heterocycles

  摘要：

  Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions beta to N. The Boc group call be removed on thermolysis or left intact during subsequent transformations.

  DOI：

  10.1021/jo901822b

文献信息

• Design, synthesis and biological evaluation of pyrazolo[3,4-d]pyrimidine-based protein kinase D inhibitors
  作者：Philippe Gilles、Rudra S. Kashyap、Maria João Freitas、Sam Ceusters、Koen Van Asch、Anke Janssens、Steven De Jonghe、Leentje Persoons、Mathias Cobbaut、Dirk Daelemans、Johan Van Lint、Arnout R.D. Voet、Wim M. De Borggraeve

  DOI：10.1016/j.ejmech.2020.112638

  日期：2020.11

  multiple roles of protein kinase D (PKD) in various cancer hallmarks have been repeatedly reported. Therefore, the search for novel PKD inhibitors and their evaluation as antitumor agents has gained considerable attention. In this work, novel pyrazolo[3,4-d]pyrimidine based pan-PKD inhibitors with structural variety at position 1 were synthesized and evaluated for biological activity. Starting from 3-IN-PP1

  蛋白激酶D（PKD）在各种癌症特征中的多重作用已被反复报道。因此，寻找新型PKD抑制剂及其作为抗肿瘤药的评价已引起了广泛的关注。在这项工作中，合成了新颖的基于吡唑并[3,4- d ]嘧啶的泛PKD抑制剂，其在位置1具有结构多样性，并对其生物学活性进行了评估。从3-IN-PP1（一种已知的PKD抑制剂，IC 50值在94-108 nM范围内）出发，发现化合物17m对PKD具有改善的生化抑制活性（IC 50 = 17-35 nM）。随后的细胞分析表明3-IN-PP1和17m抑制PKD依赖的cortactin磷酸化。此外，3-IN-PP1对PANC-1细胞显示出有效的抗增殖活性。最后，针对不同癌细胞系的筛选表明3-IN-PP1是一种有效且用途广泛的抗肿瘤药。
• Ni-Catalyzed Traceless, Directed C3-Selective C–H Borylation of Indoles
  作者：Ya-Ming Tian、Xiao-Ning Guo、Zhu Wu、Alexandra Friedrich、Stephen A. Westcott、Holger Braunschweig、Udo Radius、Todd B. Marder

  DOI：10.1021/jacs.0c05434

  日期：2020.7.29

  A highly efficient and general protocol for traceless, directed C3-selective C-H borylation of indoles with [Ni(IMes)2] as the catalyst is reported. Activation and borylation of N-H bonds by [Ni(IMes)2] is essential to install a Bpin moiety at the N-position as a traceless directing group, which enables the C3-selective borylation of C-H bonds. The N-Bpin group which is formed is easily converted in

  报告了一种以 [Ni(IMes)2] 作为催化剂对吲哚进行无痕、定向 C3 选择性 CH 硼酸化的高效通用方案。[Ni(IMes)2] 对 NH 键的活化和硼化对于在 N 位安装 Bpin 部分作为无痕导向基团至关重要，这使得 CH 键的 C3 选择性硼化成为可能。形成的 N-Bpin 基团很容易通过 [Ni(IMes)2] 的氧化加成产物和原位生成的 HBpin 原位转化回 NH 基团。催化反应操作简单，允许各种取代吲哚与 B2pin2 以优异的产率和高选择性进行硼化反应。CH硼化之后可以在整个两步中进行 C-硼化吲哚的 Suzuki-Miyaura 交叉偶联，
• HETEROCYCLIC COMPOUNDS AND METHODS OF USE
  申请人：Medivation Technologies, Inc.

  公开号：US20150065519A1

  公开（公告）日：2015-03-05

  This disclosure provides compounds and methods of using those compounds to treat metabolic disorders and hyperproliferative disorders, including administration of the compounds in conjunction with hormone receptor antagonists.

  本公开提供了化合物及其使用方法，用于治疗代谢性疾病和增生性疾病，包括与激素受体拮抗剂一起给予化合物的治疗方法。
• Iridium-catalyzed C–H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: regioselective synthesis of heteroarylboronates
  作者：Jun Takagi、Kazuaki Sato、John F Hartwig、Tatsuo Ishiyama、Norio Miyaura

  DOI：10.1016/s0040-4039(02)01135-8

  日期：2002.8

  The C–H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80–100°C in the presence of a 1/2[IrCl(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including

  芳香族杂环与双（频哪醇）二硼烷的C–H偶联是在80–100°C的辛烷中，在存在1/2 [IrCl（COD）] 2-（4,4'-二酯的条件下进行的-2，2'-联吡啶-丁基）催化剂（3mol％）。五元底物（例如噻吩，呋喃，吡咯及其苯并稠合衍生物）的反应仅生成2硼化产物，而六元杂环（包括吡啶和喹啉）的反应则选择性地在3位发生。还通过使用几乎等摩尔量的底物和二硼来实现双（硼基）杂芳族化合物的区域选择性合成。
• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS MÉTHODES D'UTILISATION
  申请人：CHAKRAVARTY SARVAJIT

  公开号：WO2015031650A1

  公开（公告）日：2015-03-05

  This disclosure provides compounds and methods of using those compounds to treat metabolic disorders and hyperproliferative disorders, including administration of the compounds in conjunction with hormone receptor antagonists. Compounds of the invention may also find use in treating cancer. Presented herein are novel compounds bearing a perhaloalkylsulfonamide moiety. Such compounds, in addition to being highly effective SREBP inhibitors, are also unexpectedly highly bioavailable in vivo. Heteroaromatic compounds bearing sulfonamide groups are prone to several ionic states, based on the inherent pKa values.

  本公开提供了化合物及使用这些化合物治疗代谢性疾病和增生性疾病的方法，包括将这些化合物与激素受体拮抗剂一起使用。发明的化合物也可以用于治疗癌症。这里提供了一种新颖的含有全卤烷磺酰胺基团的化合物。这些化合物不仅是高效的SREBP抑制剂，而且在体内意外地具有高生物利用度。含有磺酰胺基团的杂环芳香化合物易于根据固有的pKa值呈现多种离子态。