(S)-3-N-叔丁氧羰基氨基丁胺盐酸盐 | 176982-57-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (S)-3-N-叔丁氧羰基氨基丁胺盐酸盐
• 中文别名: (S)-3-boc-氨基丁胺
• 英文名称: (S)-N³-(tert-butyloxycarbonyl)-1,3-diaminobutane
• 英文别名: Tert-butyl N-[(2S)-4-aminobutan-2-YL]carbamate
• CAS: 176982-57-3
• 化学式: C₉H₂₀N₂O₂
• 分子量: 188.27
• InChiKey: JOFFSNZHLGGAJC-ZETCQYMHSA-N

物化性质

• 熔点：
  180-183°C
• 沸点：
  282.6±23.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (3-Amino-1-methyl-propyl)-carbamic acid tert-butyl ester
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: (3-Amino-1-methyl-propyl)-carbamic acid tert-butyl ester
CAS number: 176982-57-3

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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: C9H20N2O2
Molecular weight: 188.3

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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：

  (S)-3-N-叔丁氧羰基氨基丁胺盐酸盐 在 镍 sodium tetrahydroborate 、 3 A molecular sieve 、 氨 、 氢气 、 sodium carbonate 、 potassium iodide 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 正丁醇 为溶剂， 20.0 ℃ 、600.0 kPa 条件下， 反应 58.0h， 生成 [21-[[(1,1-dimethylethoxy)carbonyl]amino]-1,25,25-trimethyl-10,12,23-trioxo-4-(phenylmethyl)-24-oxa-4,9,13,20,22-pentaaza-21-hexacosen-1-yl]carbamic acid, 1,1-dimethylethyl ester (S)
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine "D" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60e which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm991043x
• 作为产物：
  描述：

  (2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate 在 镍 氨 、 氢气 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 20.0~45.0 ℃ 、600.0 kPa 条件下， 反应 30.0h， 生成 (S)-3-N-叔丁氧羰基氨基丁胺盐酸盐
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine "D" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60e which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm991043x

文献信息

• Practical and scalable synthesis of orthogonally protected-2-substituted chiral piperazines
  作者：Srinivas Chamakuri、Manuj M. Shah、David C. H. Yang、Conrad Santini、Damian W. Young

  DOI：10.1039/d0ob01713b

  日期：——

  orthogonally protected, enantiomerically pure 2-substituted piperazines is described. Starting from α-amino acids, within four steps chiral 2-substituted piperazines are obtained. The key transformation involves an aza-Michael addition between an orthogonally bis-protected chiral 1,2-diamine and the in situ generated vinyl diphenyl sulfonium salt derived from 2-bromoethyl-diphenylsulfonium triflate

  描述了一种正交保护的、对映体纯的 2-取代哌嗪的合成路线。从 α-氨基酸开始，在四步内获得手性 2-取代哌嗪。关键的转化涉及正交双保护手性 1,2-二胺和原位生成的由 2-溴乙基-二苯基锍三氟甲磺酸盐衍生的乙烯基二苯基锍盐之间的氮杂迈克尔加成。进行了使用不同保护基团的进一步验证以及多克规模的合成。该方法还应用于手性1,4-二氮杂环己烷和1,4-二氮杂环己烷的构建。此外，该方法用于手性米氮平的正式合成。
• Entropy-Controlled Catalytic Asymmetric 1,4-Type Friedel-Crafts Reaction of Phenols Using Conformationally Flexible Guanidine/Bisthiourea Organocatalyst
  作者：Yoshihiro Sohtome、Bongki Shin、Natsuko Horitsugi、Rika Takagi、Keiichi Noguchi、Kazuo Nagasawa

  DOI：10.1002/anie.201003172

  日期：——

  Soft and weak cooperation: Conformationally flexible organic compounds were found to promote the title transformation. These “soft” organocatalysts, which are able to control processes through the differential activation entropies (ΔΔS≠S−R) of the reactive intermediates, lead to high stereoselectivities without the requirement of fine‐tuning the reaction temperatures (see scheme).

  软弱合作：构象灵活的有机化合物可促进标题转换。这些“软”有机催化剂，其能够控制通过差动活化熵（ΔΔ过程小号≠小号- - [R ）的活性中间体导致高的立体选择性，而不微调反应温度的要求（见方案）。
• Synthesis of novel optical isomers of α-methylpolyamines
  作者：Nikolay A. Grigorenko、Alex R. Khomutov、Tuomo A. Keinänen、Aki Järvinen、Leena Alhonen、Juhani Jänne、Jouko Vepsäläinen

  DOI：10.1016/j.tet.2006.12.065

  日期：2007.3

  Earlier unknown (R)- and (S)-α-methylspermidine, (R)- and (S)-α-methylspermine, (R,R)-, (S,S)-, and (R,S)-α,ω-dimethylspermine were synthesized in gram scale from readily available (R)- and (S)-2-aminopropanols in high overall yields.

  早期未知的（R）-和（S）-α-甲基亚精胺，（R）-和（S）-α-甲基亚精胺，（R，R）-，（S，S）-和（R，S）-α从容易获得的（R）-和（S）-2-氨基丙醇以克级合成γ-ω-二甲基精胺，总收率高。
• Enantioselective synthesis of (R)- and (S)-3-methylspermidines
  作者：M. A. Khomutov、T. A. Keinanen、M. T. Hyvonen、J. Weisell、J. Vepsalainen、L. Alhonen、S. N. Kochetkov、A. R. Khomutov

  DOI：10.1134/s1068162015050064

  日期：2015.9

  Earlier unknown enantiomerically pure (R)- and (S)-1,8-diamino-3-methyl-4-azaoctane's (3-MeSpd's) were synthesized with high overall yields and optical purity starting from commercially available R- and S-isomers of N-Boc-2-aminopropanol-1. Application of R- and S-isomers of 3-MeSpd for the investigation of the stereospecificity of spermidine transporter and peculiarities of deoxyhypusine synthase

  从市售的R和S异构体开始，以较高的总收率和光学纯度合成了未知的对映体纯的（R）-和（S）-1,8-二氨基-3-甲基-4-氮杂辛烷（3-MeSpd）。 N-Boc-2-氨基丙醇-1。讨论了3-MeSpd的R-和S-异构体在亚精胺转运蛋白立体特异性和脱氧水苏氨酸合酶反应特性研究中的应用。
• Synthesis of (3R,10R)- and (3S,10S)-Diastereomers of 3,10-Dimethylspermine
  作者：M. A. Khomutov、M. T. Hyvönen、A. I. Salikhov、A. O. Chizhov、I. M. Ryzhov、S. N. Kochetkov、J. Vepsäläinen、T. A. Keinänen、A. R. Khomutov

  DOI：10.1134/s1068162020060126

  日期：2020.11

  Abstract A simple and practical 10-step synthesis is reported for previously unknown diastereomers of C‑methylated spermine (Spm) analogue, 1,12-diamino-3,10-dimethyl-4,9-diazadodecane (3,10-Me2Spm), starting from commercially available enantiomers of 2-(Boc-amino)-1-propanol. Title compounds were prepared in gram scale, in excellent overall yields and enantiomeric purity. Since biochemical properties

  摘要 据报道，C-甲基化精胺（Spm）类似物1,12-二氨基-3,10-二甲基-4,9-二氮十二烷（3,10-Me 2 Spm）的先前非对映异构体的合成简单而实用从2-（Boc-氨基）-1-丙醇的对映异构体开始。标题化合物以克级制备，具有优异的总收率和对映体纯度。由于可以通过改变手性中心的构型来调节3,10‑Me 2 Spm的生化特性，因此这些类似物不仅对研究精胺的细胞功能，甚至对与精胺代谢紊乱有关的疾病都有研究价值。 。