N-(1-苄基-2-肼基-2-氧乙基)氨基甲酸叔丁酯 | 30189-48-1

• 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: N-(1-苄基-2-肼基-2-氧乙基)氨基甲酸叔丁酯
• 英文名称: (S)-tert-butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate
• 英文别名: Boc-L-phenylalanine hydrazide；tert-butyl N-[(2S)-1-hydrazinyl-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 30189-48-1
• 化学式: C₁₄H₂₁N₃O₃
• 分子量: 279.339
• InChiKey: GHSCWLGHLYTNJH-NSHDSACASA-N

物化性质

• 熔点：
  131-136°C
• 沸点：
  505.3±50.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  -20°C下，应避光保存在惰性气体环境中。

SDS

Name:	tert-Butyl N-(1-benzyl-2-hydrazino-2-oxoethyl)carbamate 97% Material Safety Data Sheet
Synonym:	N-(tert-Butoxycarbonyl)-L-phenylalanine acid hydrazid
CAS:	30189-48-1

Section 1 - Chemical Product MSDS Name:tert-Butyl N-(1-benzyl-2-hydrazino-2-oxoethyl)carbamate 97% Material Safety Data Sheet
Synonym:N-(tert-Butoxycarbonyl)-L-phenylalanine acid hydrazid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
30189-48-1	tert-Butyl N-(1-benzyl-2-hydrazino-2-o	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 30189-48-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 131 - 136 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C14H21N3O3
Molecular Weight: 279

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, acids, acid chlorides.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 30189-48-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
tert-Butyl N-(1-benzyl-2-hydrazino-2-oxoethyl)carbamate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 30189-48-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 30189-48-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 30189-48-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-(1-苄基-2-肼基-2-氧乙基)氨基甲酸叔丁酯 在 盐酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 6.42h， 生成
  参考文献：
  名称：

  天冬氨酸蛋白酶内硫酶抑制剂的片段连接和优化：动态组合化学促进的基于片段的药物设计

  摘要：

  基于片段的药物设计（FBDD）为生物靶标提供活性化合物。虽然通过片段增长/优化有大量关于 FBDD 的报道，但片段链接却很少报道。动态组合化学（DCC）已成为生物靶标的强大命中识别策略。我们报告了片段连接和 DCC 的协同组合来鉴定天冬氨酸蛋白酶内硫肽酶的抑制剂。基于内硫肽素与片段复合物的 X 射线晶体结构，我们设计了双酰腙库并使用 DCC 来鉴定有效的抑制剂。最有效的抑制剂的 IC 50值为 54 nm ，与母体命中相比，效力提高了 240 倍。随后的 X 射线晶体学验证了预测的结合模式，从而证明了片段连接和 DCC 组合作为命中识别策略的效率。这种方法可以应用于一系列生物靶标，并有可能促进从命中到先导的优化。

  DOI：

  10.1002/anie.201603074
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 氨基邻苯二甲胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-(1-苄基-2-肼基-2-氧乙基)氨基甲酸叔丁酯
  参考文献：
  名称：

  氨基酸作为合成取代的1,2,4-三唑的基础

  摘要：

  我们报道了用苯甲酸银作为环化步骤的关键试剂，合成了被2或3个氨基酸侧链取代的1,2,4-三唑。描述了在合成过程中导致这些化合物的光学纯度保持率的完整研究。此外，还建立了加成环化步骤后的改进后处理，从而提高了产量并生产了不含金属的产品。

  DOI：

  10.1016/j.tet.2011.07.011

文献信息

• A convenient synthesis of 1,3,4-thiadiazole and 1,3,4-oxadiazole based peptidomimetics employing diacylhydrazines derived from amino acids
  作者：G. Nagendra、Ravi S. Lamani、N. Narendra、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2010.09.122

  日期：2010.12

  Synthesis of novel orthogonally protected 1,3,4-thiadiazole and 1,3,4-oxadiazole tethered dipeptide mimetics is described. Both the heterocycles are prepared via a set of diacylhydrazines derived from amino acids. 1,3,4-Thiadiazoles are synthesized by dehydrosulfurization using Lawesson’s reagent while 1,3,4-oxadiazoles are obtained by EDC mediated cyclodehydration.

  描述了新型的正交保护的1,3,4-噻二唑和1,3,4-恶二唑连接的二肽模拟物的合成。这两个杂环是通过一组衍生自氨基酸的二酰基肼制备的。1,3,4-噻二唑是通过使用Lawesson试剂进行脱硫而合成的，而1,3,4-恶二唑是通过EDC介导的环脱水获得的。
• [EN] COMPOUNDS AS MODULATORS OF TIGIT SIGNALLING PATHWAY<br/>[FR] COMPOSÉS MODULATEURS DE LA VOIE DE SIGNALISATION DE TIGIT
  申请人：AURIGENE DISCOVERY TECH LTD

  公开号：WO2018047139A1

  公开（公告）日：2018-03-15

  The present invention relates to compound of formula (I) as therapeutic agents to modulate the TIGIT signalling pathway. The invention also encompasses the use of the compound of formula (I) or a stereoisomer thereof or a pharmaceutically acceptable salt thereof for the treatment of diseases or disorders mediated by TIGIT.

  本发明涉及一种化合物，其化学式为（I），作为调节TIGIT信号通路的治疗剂。该发明还涵盖了利用化合物（I）或其立体异构体或其药学上可接受的盐来治疗由TIGIT介导的疾病或紊乱。
• Design, Synthesis and Biological Evaluation of a Library of Thiocarbazates and Their Activity as Cysteine Protease Inhibitors
  作者：Zhuqing Liu、Michael C. Myers、Parag P. Shah、Mary Pat Beavers、Phillip A. Benedetti、Scott L. Diamond、Amos B. Smith,III、Donna M. Huryn

  DOI：10.2174/138620710791054303

  日期：2010.5.1

  Recently, we identified a novel class of potent cathepsin L inhibitors, characterized by a thiocarbazate warhead. Given the potential of these compounds to inhibit other cysteine proteases, we designed and synthesized a library of thiocarbazates containing diversity elements at three positions. Biological characterization of this library for activity against a panel of proteases indicated a significant preference for members of the papain family of cysteine proteases over serine, metallo-, and certain classes of cysteine proteases, such as caspases. Several potent inhibitors of cathepsin L and S were identified. The SAR data were employed in docking studies in an effort to understand the structural elements required for cathepsin S inhibition. This study provides the basis for the design of highly potent and selective inhibitors of the papain family of cysteine proteases.

  最近，我们鉴定出一类新型高效组织蛋白酶L抑制剂，其特点是具有硫卡巴脒头部结构。鉴于这些化合物有可能抑制其他半胱氨酸蛋白酶，我们设计并合成了一系列硫卡巴脒类化合物，这些化合物在三个位点上含有多样性元素。该化合物的生物活性鉴定结果显示，它们对木瓜蛋白酶家族的半胱氨酸蛋白酶相较于丝氨酸、金属蛋白酶以及某些类别的半胱氨酸蛋白酶（如胱天蛋白酶）表现出显著的选择性。我们鉴定出了几个高效的组织蛋白酶L和S抑制剂。通过对接研究，我们利用SAR数据来理解实现组织蛋白酶S抑制所需的结构要素。这项研究为设计高度有效且选择性的木瓜蛋白酶家族半胱氨酸蛋白酶抑制剂奠定了基础。
• Über Peptidsynthesen, XLIV1) Nachträgliche Aktivierung von Carboxyl-Derivaten durch Oxydation oder Eliminierung und ihre Anwendung zur Peptid-Synthese an fester Phase sowie zur Cyclisierung von Peptiden
  作者：Theodor Wieland、Jürgen Lewalter、Christian Birr

  DOI：10.1002/jlac.19707400104

  日期：1970.10.30

  Übertragung des Acyl-Rests auf Aminogruppen geeignet sind, was durch Synthese von Z-Glycinbenzylamid (2) und Z-Phenylalanylglycinäthylester (3) geprüft wurde**. Die Übertragung dieses Prinzips auf die feste Phase gelingt mit den Aminoacyl-Verbindungen 6 der 4-Hydrazino-benzoesäure, die an Chlormethylpolystyrol Ester-artig verankert werden. - Eine zweite Methode der nachträglichen Aktivierung besteht in der

  为了找到更好的肽环化方法，将N-保护的氨基酸和肽的羧基与酰苯连接形成二苯酰肼1或与环邻苯二甲酰肼形成O-酰基-3-羟基酞菁4。化合物1和4可以通过用N-溴-琥珀酰亚胺氧化而转化为活化的衍生物，该衍生物适合将酰基转移到氨基上，通过Z-甘氨酸苄酰胺（2）和Z-苯丙氨酰基甘氨酸乙酯的合成进行了测试酯（3）变成**。该原理向固相的转移通过4-肼基-苯甲酸的氨基酰基化合物6成功实现，该氨基酰基化合物以酯状方式锚定在氯甲基聚苯乙烯上。-后续活化的第二种方法包括将水从2,2-二苯基-乙二醇酯7消除为反应性烯醇酯，如肽2和3的合成以及Phe-（Pro）2的环化-示出了（Phe）2 -Val-（Pro）2 -D-Ala-PheOH至D-Ala-antamanid（9）。
• The solid state VCD of a novel N-acylhydrazone trifluoroacetate
  作者：Joanna E. Rode、Krzysztof Lyczko、Katarzyna Kosińska、Joanna Matalińska、Jolanta Dyniewicz、Aleksandra Misicka、Jan Cz. Dobrowolski、Piotr F.J. Lipiński

  DOI：10.1016/j.saa.2021.120761

  日期：2022.3

  N-acylhydrazone with pharmaceutical importance was subject of structural and IR/VCD investigations in the solid state. In the crystal structure, dimers of anion-cation pairs are stabilized by H-bonding and ionic interactions. Some less common interaction types, like C=N···C-NH3+ (σ-hole) interactions, hydrazone–aromatic interactions and dispersive contacts of the CF3 groups are also present in the crystal. Satisfactory

  一种具有药学重要性的新型N-酰基腙是固态结构和 IR/VCD 研究的主题。在晶体结构中，阴离子-阳离子对的二聚体通过氢键和离子相互作用稳定。一些不太常见的相互作用类型，如C=N···C-NH 3 + (σ-空穴)相互作用、腙-芳族相互作用和CF 3的分散接触基团也存在于晶体中。固态 IR 和 VCD 光谱的令人满意的再现要求在从晶体结构中切出的四聚体（四个阳离子-阴离子对）上进行量子化学计算，表现出关键的分子间相互作用。关于计算光谱和实验光谱之间的一致性，评估了十个 DFT 泛函。应用了各种缩放计算频率的方法。对于四个单独的光谱子区域，使用单独的（优化的）频率缩放因子 (FSF) 和半峰半宽度 (HWHM) 产生了最佳结果。B3PW91 泛函的实验光谱和理论光谱（根据 SimIR、SimVCD 和 SimVDF 指数）之间的最佳匹配发现了 B3PW91 泛函，但其他一些泛函紧随其后。