1-BOC-吲哚啉-5-硼酸频那醇酯 | 837392-67-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 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: 1-BOC-吲哚啉-5-硼酸频那醇酯
• 英文名称: tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate
• 英文别名: tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydroindole-1-carboxylate
• CAS: 837392-67-3
• 化学式: C₁₉H₂₈BNO₄
• 分子量: 345.247
• InChiKey: OOORQXGLIKPNDK-UHFFFAOYSA-N

物化性质

• 沸点：
  448.9±44.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)
• 溶解度：
  溶于可溶于二氯甲烷、乙酸乙酯和甲醇。

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
1-Boc-indoline-5-boronic acid pinacol ester
Product Name:
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

---

Section 3. Composition/information on ingredients.
1-Boc-indoline-5-boronic acid pinacol ester
Ingredient name:
CAS number: 837392-67-3

---

Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

---

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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C19H28BNO4
Molecular weight: 345.2

---

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：

  1-BOC-吲哚啉-5-硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 2-(二环己基膦)3,6-二甲氧基-2′,4′,6′-三异丙基-1,1′-联苯 、 [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate 、 potassium carbonate 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 生成 tert-butyl 5-(6-cyclopropaneamido-1-[[2-(trimethylsilyl)ethoxy]methyl]pyrrolo[2,3-b]pyridin-3-yl)-2,3-dihydroindole-1-carboxylate
  参考文献：
  名称：

  [EN] 7-AZAINDOLE COMPOUNDS FOR INHIBITION OF BCR-ABL TYROSINE KINASES
  [FR] COMPOSÉS DE 7-AZAINDOLE POUR L'INHIBITION DE TYROSINE KINASES BCR-ABL

  摘要：

  本公开涉及抑制Bcr-Abl酪氨酸激酶的化合物和组合物，制备该化合物和组合物的方法，以及它们在治疗各种癌症，如慢性髓细胞白血病（CML）中的使用。

  公开号：

  WO2022076973A1
• 作为产物：
  描述：

  5-溴二氢吲哚 在 4-二甲氨基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 27.0h， 生成 1-BOC-吲哚啉-5-硼酸频那醇酯
  参考文献：
  名称：

  5-（2,3-二氢-1 H-吲哚-5-基）-7 H-吡咯并[2,3- d ]嘧啶-4-胺衍生物作为新型的受体相互作用蛋白激酶1（ RIPK1）抑制剂，在肿瘤转移模型中显示有效活性

  摘要：

  我们在这里报告了5-（2,3-dihydro-1 H-吲哚-5-基）-7 H-吡咯并[2,3- d ]嘧啶-4-胺衍生物的结构优化和构效关系研究。新型的受体相互作用蛋白激酶1（RIPK1）抑制剂。在所有获得的RIPK1抑制剂中，1-（5- {4-氨基-7-乙基-7 H-吡咯并[2,3- d ]嘧啶-5-基} -2,3-二氢-1 H-吲哚-1 -基）-2- [3-（三氟甲氧基）苯基]乙-1-酮（22b）是最活跃的。该化合物以0.004μM的结合亲和力（K D）和酶促IC 50有效抑制RIPK1值为0.011μM，并且还显示出良好的激酶选择性。它可以有效地保护细胞免于坏死性坏死，并减轻肿瘤细胞在体外和体内诱导的血管内皮细胞的坏死细胞死亡。重要的是，化合物22b在实验性B16黑色素瘤肺转移模型中显示出优异的抗转移活性。它还显示出良好的药代动力学性质。总体而言，22b可能是预防肿瘤转移的有前途的药物。

  DOI：

  10.1021/acs.jmedchem.8b01652

文献信息

• Synthesis and Pharmacological Evaluation of Noncatechol G Protein Biased and Unbiased Dopamine D1 Receptor Agonists
  作者：Pingyuan Wang、Daniel E. Felsing、Haiying Chen、Sweta R. Raval、John A. Allen、Jia Zhou

  DOI：10.1021/acsmedchemlett.9b00050

  日期：2019.5.9

  recruitment in HEK293 cells. Here, we report the chemical synthesis, pharmacological evaluation, and molecular docking studies leading to the identification of two novel noncatechol D1R agonists that are a subnanomolar potent unbiased ligand 19 (PW0441) and a nanomolar potent complete G protein biased ligand 24 (PW0464), respectively. These novel D1R agonists provide important tools to study D1R activation and

  非儿茶酚杂环化合物最近被发现是具有优越药代动力学特性的强效和选择性 G 蛋白偏向多巴胺 1 受体 (D1R) 激动剂。为了确定以 G 蛋白或 β-arrestin 信号偏倚为中心的构效关系，围绕先导化合物 5 (PF2334) 的三个芳香药效团采用了系统的药物化学，生成了一系列新分子，这些分子在 D1R Gs- HEK293 细胞中依赖 cAMP 信号传导和 β-抑制蛋白募集。在这里，我们报告了化学合成、药理学评估和分子对接研究，这些研究导致了两种新型非儿茶酚 D1R 激动剂的鉴定，它们是亚纳摩尔强效无偏配体 19 (PW0441) 和纳摩尔强效完全 G 蛋白偏向配体 24 (PW0464)，分别。
• INHIBITORS OF FIBROBLAST ACTIVATION PROTEIN
  申请人：Praxis Biotech LLC

  公开号：US20190185451A1

  公开（公告）日：2019-06-20

  Compounds and compositions for modulating fibroblast activation protein (FAP) are described. The compounds and compositions may find use as therapeutic agents for the treatment of diseases, including hyperproliferative diseases.

  描述了用于调节成纤维细胞活化蛋白（FAP）的化合物和组合物。这些化合物和组合物可能被用作治疗疾病的治疗剂，包括高增殖性疾病。
• Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem
  作者：Julien C. Vantourout、Robert P. Law、Albert Isidro-Llobet、Stephen J. Atkinson、Allan J. B. Watson

  DOI：10.1021/acs.joc.6b00466

  日期：2016.5.6

  The Chan–Evans–Lam reaction is a valuable C–N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan–Evans–Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found

  Chan–Evans–Lam反应是有价值的C–N键形成过程。但是，芳基硼酸频哪醇（BPin）酯试剂可能很难成为偶合剂，常常导致收率低，特别是在与芳基胺反应时。在此，我们报告了烷基-芳基胺与芳基BPin的Chan-Evans-Lam胺化反应的有效反应条件。发现混合的MeCN / EtOH溶剂系统可以使用芳基胺形成有效的C–N键，而烷基胺的偶联则不需要EtOH。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：STEP PHARMA S A S

  公开号：WO2019106156A1

  公开（公告）日：2019-06-06

  Compounds of formula (I): (I) and related aspects.

  式(I)的化合物及相关方面。
• [EN] BICYCLIC HETEROARYL COMPOUNDS AS GPR119 RECEPTOR AGONISTS<br/>[FR] COMPOSÉS HÉTÉROARYLES BICYCLIQUES EN TANT QU'AGONISTES DU RÉCEPTEUR GPR119
  申请人：CENTAURUS BIOPHARMA CO LTD

  公开号：WO2012103806A1

  公开（公告）日：2012-08-09

  The present invention provides a new class of bicyclic heteroaryl compounds represented by Formula (I), pharmaceutical compositions containing these compounds, and their use for modulating the activity of GPR119 in the treatment of metabolic disorders and complications thereof, as well as methods for the treatment of the metabolic disorders and complications thereof.

  本发明提供了一类新的双环杂环芳基化合物，其化学式表示为（I），包含这些化合物的药物组合物，以及它们在调节GPR119活性以治疗代谢紊乱及其并发症方面的用途，以及治疗代谢紊乱及其并发症的方法。