L-苯甘氨酸叔丁酯盐酸盐 | 161879-12-5

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: L-苯甘氨酸叔丁酯盐酸盐
• 中文别名: L-苯甘氨酸-叔丁酯盐酸盐；D-苯甘氨酸叔丁酯盐酸盐
• 英文名称: phenylglycine tert-butyl ester hydrochloride
• 英文别名: L-phenylglycine tert-butyl ester hydrochloride；L-phenylglycine t-butyl ester hydrochloride；(S)-tert-butyl 2-amino-2-phenylacetate hydrochloride；tert-butyl (2S)-2-amino-2-phenylacetate;hydrochloride
• CAS: 161879-12-5
• 化学式: C₁₂H₁₇NO₂*ClH
• 分子量: 243.733
• InChiKey: CBYKTKOQAVJTOU-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  保存方法：存放在-15°C环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Phg-OtBu HCl
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: H-Phg-OtBu HCl
CAS number: 161879-12-5

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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.
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: C12H17NO2.ClH
Molecular weight: 243.7

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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 chloride.

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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

制备方法与用途

H-Phg-OtBu是一种化合物。HCl是甘氨酸（HY-Y0966）的衍生物。

反应信息

• 作为反应物：
  描述：

  L-苯甘氨酸叔丁酯盐酸盐 在 palladium on activated charcoal 异丁腈 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 27.0h， 生成 N-(diazoacetyl)-L-alanine-N-[(1S)-2-tert-butoxy-2-oxo-1-phenylethyl]amide
  参考文献：
  名称：

  通过天冬氨酸活化为早老素1设计的抑制剂。初步沟通

  摘要：

  γ-分泌酶是一种对阿尔茨海默氏痴呆症至关重要的多蛋白天冬氨酸蛋白酶，目前尚无法用于NMR实验，到目前为止，它已经摆脱了结晶现象。用反应性探针对天冬氨酸蛋白酶进行位置扫描可为药物开发提供必要的结构信息。在这里，我们描述了基于已知的酶抑制剂DAPT（酸不稳定的化合物的合成1），例如，N-末端官能化重氮化合物4或C-末端酸不稳定（环丙基甲基）酯11，其被设计成反应在天冬氨酸蛋白酶早老蛋白1的特定酸性活性位点环境。对酸不稳定的DAPT类似物11 – 13实际上，在无细胞的γ-分泌酶测定中显示出强烈的抑制作用。

  DOI：

  10.1002/hlca.200490208
• 作为产物：
  描述：

  tert-Butyl phenylglycinate hydrochloride 在 chiral stationary phase including isopropyl-functionalized CF₆ 作用下， 以 乙醇 、 正庚烷 、 三氟乙酸 为溶剂， 生成 (R)-tert-butyl 2-amino-2-phenylacetate hydrochloride 、 L-苯甘氨酸叔丁酯盐酸盐
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS
  [FR] COMPOSITIONS ET PROCÉDÉS POUR DES CYCLOFRUCTANES EN TANT QU'AGENTS DE SÉPARATION

  摘要：

  公开号：

  WO2010148191A3

文献信息

• Primary Amine-Thioureas with Improved Catalytic Properties for “Difficult” Michael Reactions: Efficient Organocatalytic Syntheses of (S)-Baclofen, (R)-Baclofen and (S)-Phenibut
  作者：Michail Tsakos、Christoforos G. Kokotos、George Kokotos

  DOI：10.1002/adsc.201100636

  日期：2012.3

  Among the class of primary amine‐thioureas based on tert‐butyl esters of α‐amino acids, the most efficient organocatalyst for “difficult” Michael reactions was identified. The derivative based on (S)‐di‐tert‐butyl aspartate and (1R,2R)‐diphenylethylenediamine provided the products of the reaction between aryl methyl ketones and nitroolefins in excellent yields and enantioselectivities. In addition

  在基于α-氨基酸叔丁基酯的伯胺硫脲类中，发现了“难”迈克尔反应最有效的有机催化剂。基于（S）-二叔丁基天冬氨酸盐和（1 R，2 R）-二苯基乙二胺的衍生物提供了芳基甲基酮与硝基烯烃之间反应的产物，收率和对映选择性极好。另外，这种新催化剂可以以低催化剂负载量（5mol％）使用。有效合成（S）-baclofen，（R）-baclofen和（S）-phenibut的方法突显了这种方法的实用性。
• Epimerization-Free C-Term Activation of Peptide Fragments by Ball Milling
  作者：Yves Yeboue、Marion Jean、Gilles Subra、Jean Martinez、Frédéric Lamaty、Thomas-Xavier Métro

  DOI：10.1021/acs.orglett.0c03209

  日期：2021.2.5

  Peptides were produced in high yields and, if any, very low epimerization, by mechanochemical coupling of peptide fragments containing highly epimerization-prone and/or highly hindered amino acids at C-term. Ball milling was clearly identified as the key element enabling one to obtain such results.

  通过在 C 端含有高度差向异构化和/或高度受阻氨基酸的肽片段的机械化学偶联，以高产率和（如果有的话）非常低的差向异构化产生肽。球磨被清楚地确定为获得这种结果的关键因素。
• 2,2′-dithiobisbenzamides derived from α-, β- and γ-amino acids possessing anti-HIV activities: synthesis and structure–activity relationship
  作者：J.V.N Vara Prasad、Joseph A Loo、Frederick E Boyer、Michael A Stier、Rocco D Gogliotti、William J Turner、Patricia J Harvey、Melissa R Kramer、David P Mack、Jefferey D Scholten、Stephen J Gracheck、John M Domagala

  DOI：10.1016/s0968-0896(98)00118-7

  日期：1998.10

  2'-dithiobisbenzamides derived from alpha-, beta- and gamma-amino acids. Electrospray ionization mass spectrometry was used to study the zinc-ejection activity of these compounds. Among the alpha-amino acid derived 2,2'-dithiobisbenzamides, analogues containing alkyl side chains were found to be antivirally active with good therapeutic indices. 2,2'-Dithiobisbenzamides, derived from beta- and gamma-amino

  含有高度保守的逆转录病毒锌指的核衣壳蛋白（NCp7）在人类免疫缺陷病毒（HIV）生命周期的早期和晚期都是必不可少的，并且是AIDS治疗的新目标。HIV-1 NCp7是基本的55个氨基酸氨基酸蛋白，在两侧各含两个C（X）2C（X）4H（X）4C基序锌指。先前已报道2,2'-二硫代双苯甲酰胺从这些NCp7锌指中释放锌，并抑制HIV复制。具体而言，衍生自简单氨基酸的2,2'-二硫代双苯甲酰胺显示出良好的抗病毒活性。苯并异噻唑酮3（2的环状衍生物）被选为临床试验中的艾滋病治疗剂。本文中我们报告了2,2'的合成和抗病毒活性，包括治疗指数 衍生自α-，β-和γ-氨基酸的β-二硫代双苯甲酰胺。电喷雾电离质谱法用于研究这些化合物的锌喷射活性。在α-氨基酸衍生的2,2'-二硫代双苯甲酰胺中，发现含有烷基侧链的类似物具有良好的治疗指数，具有抗病毒活性。发现衍生自β-和γ-氨基酸的2,2'-二硫代双苯甲酰胺比α
• Potent 7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid-Based Macrocyclic Inhibitors of Hepatitis C Virus NS3 Protease
  作者：Kevin X. Chen、F. George Njoroge、John Pichardo、Andrew Prongay、Nancy Butkiewicz、Nanhua Yao、Vincent Madison、Viyyoor Girijavallabhan

  DOI：10.1021/jm050520a

  日期：2006.1.1

  The NS3 protease of hepatitis C virus (HCV) has emerged as one of the best characterized targets for next-generation HCV therapy. The tetrapeptide 1 and pentapeptide 2 are alpha-ketoamide-type HCV serine protease inhibitors with modest potency. We envisioned that the 1,2,3,4-tetrahydroisoquinoline-3-carboxylamide (Tic) moiety could be cyclized to the P3 capping group. The resulting macrocycle could

  丙型肝炎病毒（HCV）的NS3蛋白酶已成为下一代HCV治疗的最有特色的靶标之一。四肽1和五肽2是具有中等效力的α-酮酰胺型HCV丝氨酸蛋白酶抑制剂。我们设想了1,2,3,4-四氢异喹啉-3-羧酰胺（Tic）部分可以被环化为P3封端基团。所得的大环化合物可通过其与Ala156甲基的额外接触来增强结合。大环化还可以提供肽含量较低的HCV抑制剂。从二肽5开始合成，其是通过两个氨基酸衍生物的偶联而获得的。将N-末端封端为庚-6-烯酰胺，得到6。双键的氢硼化得到醇7，大环8的前体。在Mitsunobu条件下实现了大环化（PPh（3），ADDP）。然后，将大环酸9与适当的右侧片段12、14或16结合，该片段由共同的中间体11制备。最后，α-羟酰胺的氧化提供了目标分子α-酮酰胺17、18和21。然后将末端酯加工成羧酸19和20，以及酰胺20和23。在HCV NS3蛋白酶连续测定中测试了抑制剂17-23。
• Design, Synthesis, and Biological Activity of <i>m</i>-Tyrosine-Based 16- and 17-Membered Macrocyclic Inhibitors of Hepatitis C Virus NS3 Serine Protease
  作者：Kevin X. Chen、F. George Njoroge、John Pichardo、Andrew Prongay、Nancy Butkiewicz、Nanhua Yao、Vincent Madison、Viyyoor Girijavallabhan

  DOI：10.1021/jm050323b

  日期：2005.10.1

  weak HCV inhibitors with a binding constant, Ki, above 5 microM. We envisioned that cyclization of a P2 phenyl side chain to a P3 capping group could enhance binding through an interaction of the resulting macrocycle with the methyl group of Ala156 on the enzyme backbone. The macrocyclic dipeptide moiety would also decrease the peptidic nature of the inhibitors. The synthesis of macrocyclic HCV inhibitors

  当前用于治疗丙型肝炎病毒（HCV）感染的疗法的有限的功效和相当大的副作用促使人们为开发安全有效的新疗法做出了巨大的努力。1型五肽α-酮酰胺是弱HCV抑制剂，其结合常数Ki大于5 microM。我们预想到，P2苯基侧链与P3封端基的环化可以通过所得大环与酶骨架上Ala156的甲基相互作用而增强结合。大环二肽部分也将降低抑制剂的肽性质。大环HCV抑制剂的合成从间酪氨酸甲酯开始。两次连续的偶联，首先是与Boc-环己基甘氨酸偶联，然后是与hept-6-烯酸偶联，得到化合物6。烯烃通过硼氢化反应转化为醇。酚醇7的关键大环化是通过Mitsunobu反应实现的。准备了16元和17元大环（8和21）。水解后，将大环酸（15和22）与右手三肽（14）偶联，得到α-羟酰胺，在Dess-Martin的高碘烷氧化后，它提供了所需的α-酮酰胺。在这些肽的C-末端掺入了酯，酸和酰胺。这些抑制剂在HCV蛋白酶连续测定中