叔丁基3-溴甲基-吲哚-1-羧酸酯 | 96551-21-2

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 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: 叔丁基3-溴甲基-吲哚-1-羧酸酯
• 中文别名: 3-溴甲基-吲哚-1-羧酸叔丁酯
• 英文名称: 1-(t-butyloxycarbonyl)-3-(bromomethyl)indole
• 英文别名: tert-butyl 3-(bromomethyl)-1H-indole-1-carboxylate；1-(tert-butoxycarbonyl)-3-(bromomethyl) indole；tert-butyl 3-(bromomethyl)indole-1-carboxylate
• CAS: 96551-21-2
• 化学式: C₁₄H₁₆BrNO₂
• mdl: MFCD05864361
• 分子量: 310.191
• InChiKey: NRFDZZBPGMUOQD-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C
• 沸点：
  391.1±34.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P501,P260,P270,P264,P280,P303+P361+P353,P301+P330+P331,P363,P301+P312+P330,P304+P340+P310,P305+P351+P338+P310,P405
• 危险品运输编号：
  3261
• 危险性描述：
  H302,H314

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl 3-bromomethylindole-1-carboxylate
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: tert-Butyl 3-bromomethylindole-1-carboxylate
CAS number: 96551-21-2

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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.

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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.

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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.

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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, refrigerated.
Storage:

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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.

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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: C14H16BrNO2
Molecular weight: 310.2

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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, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  叔丁基3-溴甲基-吲哚-1-羧酸酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 以27%的产率得到tert-butyl 3-((1,3-dioxoisoindolin-2-yloxy)methyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  WO2008/8398

  摘要：

  公开号：
• 作为产物：
  描述：

  3-甲酰基吲哚酸-1-羧酸 t-丁基酯 在 sodium tetrahydroborate 、 四溴化碳 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 叔丁基3-溴甲基-吲哚-1-羧酸酯
  参考文献：
  名称：

  （2R，4R）-Monatin的简明合成。

  摘要：

  莫纳甜（Monatin）4-羟基-4-（3-吲哚基甲基）-谷氨酸是一种天然存在的甜氨基酸。已经发现（2R，4R）-莫纳甜异构体是其四种立体异构体中最甜的。通过（4R）-N-叔丁氧基羰基（tBoc）-4-叔丁基二甲基甲硅烷氧基-D-焦谷氨酸甲酯与3-叔丁基的烷基化反应完成（2R，4R）-莫纳甜的简洁高效合成（溴甲基）-1H-吲哚-1-羧酸酯得到（4R）-N-tBoc-4-叔丁基二甲基甲硅烷氧基-4-（N-tBoc-3-吲哚基甲基）-D-焦谷氨酸甲酯（2R，4R）-莫纳甜的内酰胺形式，带有保护基。这之后是内酰胺环的水解和脱保护。已证明4-羟基D-焦谷氨酸衍生物是有效制备（2R，4R）-莫纳甜具有较高的光学纯度，因为烷基化在C4处以区域选择性和立体选择性方式进行，形成了适当的不对称四取代碳中心；然后将所得的烷基化焦谷氨酸衍生物容易地转化为莫纳甜的线性形式。

  DOI：

  10.1248/cpb.c16-00358

文献信息

• Pyrrolidine derivatives
  申请人：——

  公开号：US20020049243A1

  公开（公告）日：2002-04-25

  The present invention relates to pyrrolidine derivatives and dimeric forms and/or pharmaceutically acceptable esters, and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in treating disease states are associated with vasoconstriction of increasing occurrences.

  本发明涉及吡咯烷衍生物及其二聚体形式和/或药用可接受的酯和/或盐。这些化合物可用作金属蛋白酶抑制剂，例如锌蛋白酶，特别是锌水解酶，对治疗与血管收缩增加发生相关的疾病状态有效。
• Enantioselective Enzymatic Reduction of Acrylic Acids
  作者：Chihui An、Megan H. Shaw、Annika Tharp、Deeptak Verma、Hongming Li、Heather Wang、Xiao Wang

  DOI：10.1021/acs.orglett.0c02959

  日期：2020.11.6

  identified, and optimization studies led to the development of an enzymatic protocol for the reduction of α,β-unsaturated acids under mild, aqueous conditions. The substrate scope includes aromatic- and aliphatic-substituted acrylic acids, as well as cyclic α,β-substituted acrylic acids, yielding chiral α-substituted acids with exquisite levels of enantioselectivity (>99% ee).

  鉴定了具有广泛底物特异性的烯还原酶 (ERED 36)，优化研究导致开发了一种酶促方案，用于在温和的水性条件下还原 α,β-不饱和酸。底物范围包括芳香族和脂肪族取代的丙烯酸，以及环状 α,β-取代的丙烯酸，产生具有极佳对映选择性 (>99% ee) 的手性 α-取代酸。
• [EN] PHENYL-UREA AND PHENYL-CARBAMATE DERIVATIVES AS INHIBITORS OF PROTEIN AGGREGATION<br/>[FR] DÉRIVÉS DE PHÉNYLURÉE ET DE PHÉNYLCARBAMATE COMME INHIBITEURS D'AGRÉGATION DE PROTÉINE
  申请人：NEUROPORE THERAPIES INC

  公开号：WO2013148365A1

  公开（公告）日：2013-10-03

  The present invention relates to certain phenyl-urea and phenyl-carbamate derivatives, pharmaceutical compositions containing them, and methods of using them, including methods for preventing, reversing, slowing, or inhibiting protein aggregation, and methods of treating diseases that are associated with protein aggregation, including neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, Lewy body disease, and multiple system atrophy.

  本发明涉及某些苯脲和苯氨基甲酸酯衍生物，含有它们的药物组合物以及使用它们的方法，包括用于预防、逆转、减缓或抑制蛋白质聚集的方法，以及用于治疗与蛋白质聚集相关疾病的方法，包括神经退行性疾病，如帕金森病、阿尔茨海默病、路易体病和多系统萎缩。
• Structure‐Enabled Discovery of a Stapled Peptide Inhibitor to Target the Oncogenic Transcriptional Repressor TLE1
  作者：Sally McGrath、Marcello Tortorici、Ludovic Drouin、Savade Solanki、Lewis Vidler、Isaac Westwood、Peter Gimeson、Rob Van Montfort、Swen Hoelder

  DOI：10.1002/chem.201700747

  日期：2017.7.18

  transcription factors. Inhibition of this protein–protein interaction represents a putative cancer target, but no small-molecule inhibitors have been published for this challenging interface. Herein, the structure-enabled design and synthesis of a constrained peptide inhibitor of TLE1 is reported. The design features the introduction of a four-carbon-atom linker into the peptide epitope found in many TLE1 binding

  TLE1是一种致癌转录共抑制因子，通过结合转录因子发挥其抑制作用。抑制这种蛋白质间相互作用代表了一个可能的癌症靶标，但尚未有针对这一具有挑战性的界面的小分子抑制剂被发表。在本文中，报道了TLE1的受约束肽抑制剂的结构使能设计和合成。该设计的特点是在许多TLE1结合伴侣中发现的肽表位中引入了四碳原子接头。已开发出一种概念验证肽cycFWRPW的简洁合成路线。通过等温滴定热法和热位移测定法进行的生物物理测试表明，尽管受约束的肽有效结合，但其K d约高五倍。比不受约束的肽要高。共晶体结构表明，相对于无环肽原本保存良好的构象，亲和力降低可能是由于一条侧链的微小位移所致。这项工作描述了一种受约束的肽抑制剂，可以作为改进抑制剂的基础。
• Fusarochromene, a novel tryptophan-derived metabolite from <i>Fusarium sacchari</i>
  作者：James W. Marshall、Kate M. J. de Mattos-Shipley、Iman A. Y. Ghannam、Asifa Munawar、Jonathan C. Killen、Colin M. Lazarus、Russell J. Cox、Christine L. Willis、Thomas J. Simpson

  DOI：10.1039/d0ob02031a

  日期：——

  Fusarochromene and the fusarochromanone mycotoxins are derived via oxidative cleavage of the aromatic amino acid tryptophan.

  Fusarochromene和fusarochromanone霉菌毒素是通过芳香族氨基酸色氨酸的氧化裂解产生的。