5678-四氢喹啉-3-硼酸频那醇酯 | 1256360-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 5678-四氢喹啉-3-硼酸频那醇酯
• 英文名称: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline
• CAS: 1256360-50-5
• 化学式: C₁₅H₂₂BNO₂
• 分子量: 259.156
• InChiKey: JNIVVYUCVMLVLP-UHFFFAOYSA-N

物化性质

• 沸点：
  374.0±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5,6,7,8-Tetrahydroquinoline-3-boronic acid, pinacol ester
Synonyms: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline

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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: 5,6,7,8-Tetrahydroquinoline-3-boronic acid, pinacol ester
CAS number: 1256360-50-5

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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, under −20◦C.
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: C15H22BNO2
Molecular weight: 259.2

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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.

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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：

  5678-四氢喹啉-3-硼酸频那醇酯 在 copper(ll) bromide 作用下， 以 甲醇 、 水 为溶剂， 以271 mg的产率得到3-溴-5,6,7,8-四氢喹啉
  参考文献：
  名称：

  N-杂环与冻干过氧化酶催化剂的制备规模生物催化氧化

  摘要：

  来自Agrocybe aegerita (r Aae UPO-PaDa-IH)的非特异性过氧化酶变体的冻干制剂是多种N -杂环化合物氧化的高效催化剂。已开发出可扩展、高产和对映选择性生物催化氧化，包括 27 个制备实例（约 100 毫克规模），适用于广泛的底物，包括烷基吡啶、双环 N-杂环和吲哚。

  DOI：

  10.1002/anie.202214759
• 作为产物：
  描述：

  5,6,7,8-四氢喹啉 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 5678-四氢喹啉-3-硼酸频那醇酯
  参考文献：
  名称：

  Complanadines A和B的总合成

  摘要：

  两次：从（-）-乙氨酸获得二聚生物碱（（-）-complanadines A（1）和B（2）的总合成。非对称基序是通过吡啶N-氧化物的直接芳基化组装而成的。确定了Complanadines A和B的绝对构型和比旋度。Cbz ＝苄氧羰基。

  DOI：

  10.1002/anie.201208297

文献信息

• Discovery of 3-Ethyl-4-(3-isopropyl-4-(4-(1-methyl-1<i>H</i>-pyrazol-4-yl)-1<i>H</i>-imidazol-1-yl)-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridin-1-yl)benzamide (TAS-116) as a Potent, Selective, and Orally Available HSP90 Inhibitor
  作者：Takao Uno、Yuichi Kawai、Satoshi Yamashita、Hiromi Oshiumi、Chihoko Yoshimura、Takashi Mizutani、Tatsuya Suzuki、Khoon Tee Chong、Kazuhiko Shigeno、Mitsuru Ohkubo、Yasuo Kodama、Hiromi Muraoka、Kaoru Funabashi、Koichi Takahashi、Shuichi Ohkubo、Makoto Kitade

  DOI：10.1021/acs.jmedchem.8b01085

  日期：2019.1.24

  proteins, promoting cancer cell growth, and survival. A novel series of HSP90 inhibitors were discovered by structure–activity relationship (SAR)-based optimization of an initial hit compound 11a having a 4-(4-(quinolin-3-yl)-1H-indol-1-yl)benzamide structure. The pyrazolo[3,4-b]pyridine derivative, 16e (TAS-116), is a selective inhibitor of HSP90α and HSP90β among the HSP90 family proteins and exhibits

  分子伴侣热休克蛋白90（HSP90）是癌症治疗的有希望的目标，因为它有助于稳定与癌症相关的蛋白质，促进癌细胞的生长和存活。通过基于结构-活性关系（SAR）的具有4-（4-（喹啉-3-基）-1 H-吲哚-1-基）苯甲酰胺的初始命中化合物11a优化，发现了一系列新的HSP90抑制剂结构体。吡唑并[3,4- b ]吡啶衍生物16e（TAS-116）是HSP90家族蛋白中HSP90α和HSP90β的选择性抑制剂，在小鼠中可口服。16e类似物16d的X射线共晶体结构在N-末端ATP结合位点显示出独特的结合模式。口服16e在NCI-H1975异种移植小鼠模型中显示出有效的抗肿瘤作用，而体重没有明显减轻。
• Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (−)-Lycodine and (−)-Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities
  作者：Le Zhao、Chihiro Tsukano、Eunsang Kwon、Hisashi Shirakawa、Shuji Kaneko、Yoshiji Takemoto、Masahiro Hirama

  DOI：10.1002/chem.201604647

  日期：2017.1.18

  alkaloid lycodine (1) and its unsymmetric dimers, complanadines A (4) and B (5), have been developed. Regioselective construction of the bicyclo[3.3.1]nonane core structure of lycodine was achieved by a remote functionality‐controlled Diels–Alder reaction and subsequent intramolecular Mizoroki–Heck reaction. A key coupling reaction of the lycodine units, pyridine N‐oxide (66) and aryl bromide (65)

  有价值的合成路线到石松生物碱lycodine（1）和它的非对称的二聚物，complanadines A（4）和B（5），已被开发。可以通过远程功能控制的Diels-Alder反应和随后的分子内Mizoroki-Heck反应实现莱科定双环[3.3.1]壬烷核心结构的区域选择性构建。通过在66的C1位置进行CH芳基化反应，可以使lycodine单元，吡啶N-氧化物（66）和芳基溴化物（65）发生关键的偶联反应在合成后期提供了不对称的二聚体结构。该策略大大简化了二聚体体系结构和功能化的构建。Complanadines A（4）和B（5）中，通过调整单-联吡啶的氧化水平合成Ñ氧化物（67）。这种常见中间体（67）的多种用途表明在自然界中可能存在Complanadines的生物合成途径。lycodine（1）和complanadines A（4）和B（5）的对映体。）的量足以进行生物学评估。在PC-
• 并环类回旋酶和拓扑异构酶IV抑制剂
  申请人：山东轩竹医药科技有限公司

  公开号：CN105884752B

  公开（公告）日：2018-08-31

  本发明属于医药技术领域，具体涉及式(I)所示的化合物、其药学上可接受的盐、酯或其立体异构体，R1、R2、环A及环B如说明书中所定义；本发明还涉及这些化合物的制备方法、药物制剂、药物组合物及在用于制备治疗和/预防细菌感染性疾病的药物中的用途。
• Total Syntheses of Complanadines A and B
  作者：Le Zhao、Chihiro Tsukano、Eunsang Kwon、Yoshiji Takemoto、Masahiro Hirama

  DOI：10.1002/anie.201208297

  日期：2013.2.4

  Twice as nice: Total syntheses of dimeric alkaloids, (−)‐complanadines A (1) and B (2), were achieved from (−)‐lycodine. The unsymmetrical motif was assembled through direct arylation of the pyridine N‐oxide. The absolute configuration and specific rotations of complanadines A and B were identified. Cbz=Benzyloxycarbonyl.

  两次：从（-）-乙氨酸获得二聚生物碱（（-）-complanadines A（1）和B（2）的总合成。非对称基序是通过吡啶N-氧化物的直接芳基化组装而成的。确定了Complanadines A和B的绝对构型和比旋度。Cbz ＝苄氧羰基。
• Preparative‐Scale Biocatalytic Oxygenation of <i>N</i> ‐Heterocycles with a Lyophilized Peroxygenase Catalyst
  作者：Balázs Pogrányi、Tamara Mielke、Alba Díaz‐Rodríguez、Jared Cartwright、William P. Unsworth、Gideon Grogan

  DOI：10.1002/anie.202214759

  日期：2023.1.26

  A lyophilized preparation of an unspecific peroxygenase variant from Agrocybe aegerita (rAaeUPO-PaDa-I-H) is a highly effective catalyst for the oxygenation of a diverse range of N-heterocyclic compounds. Scalable, high yielding and enantioselective biocatalytic oxygenations have been developed, including 27 preparative examples (ca. 100 mg scale) across a wide range of substrates, including alkyl

  来自Agrocybe aegerita (r Aae UPO-PaDa-IH)的非特异性过氧化酶变体的冻干制剂是多种N -杂环化合物氧化的高效催化剂。已开发出可扩展、高产和对映选择性生物催化氧化，包括 27 个制备实例（约 100 毫克规模），适用于广泛的底物，包括烷基吡啶、双环 N-杂环和吲哚。