D-亮氨酸乙酯盐酸盐 | 73913-65-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 亮氨酸类衍生物
• 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: D-亮氨酸乙酯盐酸盐
• 英文名称: D-leucine ethyl ester hydrochloride
• 英文别名: ethyl L-leucinate hydrochloride；ethyl (2R)-2-amino-4-methylpentanoate;hydrochloride
• CAS: 73913-65-2
• 化学式: C₈H₁₇NO₂*ClH
• 分子量: 195.689
• InChiKey: NOUDPBCEONUCOV-OGFXRTJISA-N

物化性质

• 熔点：
  121-127℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-D-Leu-oet 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-D-Leu-oet hcl
CAS number: 73913-65-2

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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.
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: C8H17NO2.ClH
Molecular weight: 195.7

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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

反应信息

• 作为反应物：
  描述：

  D-亮氨酸乙酯盐酸盐 在 正丁基锂 、 sodium ethanolate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.42h， 生成 (2R)-4-acetyl-1,2-dihydro-5-hydroxy-2-(2-methylpropyl)-1-[(2E)-1-oxodec-2-enyl]-3H-pyrrol-3-one
  参考文献：
  名称：

  通过Dieckmann缩合反应合成抗生素（R）-Reutericyclin 。

  摘要：

  （R）-Reutericyclin（（R）-1）是具有三取代的四酸部分的杀菌两亲天然产物，它是由D-亮氨酸分四个步骤制备的，总收率为24％。的手性杂环部分1是由合成迪克曼的乙基环化ñ - （乙酰乙酰基）亮氨酸（7），将得到的吡咯衍生物8被Ñ -acylated与（Ë在丁基锂在存在下） -癸-2-烯酰氯− 70°（方案2）。该新方法简单明了，并且可以合成约200个对映体过量（ee）的路透环素的两个对映体。80％。

  DOI：

  10.1002/hlca.200590226
• 作为产物：
  描述：

  (R)-2-((R)-2-Hydroxy-1-phenyl-ethylamino)-4-methyl-pent-4-enoic acid ethyl ester; hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以92%的产率得到D-亮氨酸乙酯盐酸盐
  参考文献：
  名称：

  手性甘氨酸烯醇酸合成子的立体选择性烷基化。α-氨基酸衍生物的对映选择性合成。

  摘要：

  描述了衍生自D-2-苯基甘氨醇的新的手性甘氨酸烯醇式合成子的高度立体选择性烷基化（％de = 99.6至97.6）。用一锅三步法对烷基化加合物进行脱保护，即可得到相应的α-氨基酸的乙酯盐酸盐，而不会发生外消旋作用。

  DOI：

  10.1016/s0040-4039(00)82269-8

文献信息

• Radical Transformation of Aliphatic C–H Bonds to Oxime Ethers via Hydrogen Atom Transfer
  作者：Xinmou Wang、Mo Yu、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.1c03087

  日期：2021.11.5

  we describe a strategy for conversion of aliphatic C–H bonds to oxime ethers via hydrogen atom transfer. In this strategy, the decatungstate anion and sulfate radical play complementary roles in the abstraction of hydrogen atoms from primary, secondary, and tertiary C–H bonds of alkanes. The easy accessibility of alkanes and the broad substrate scope, mild conditions, and excellent regioselectivity

  在此，我们描述了一种通过氢原子转移将脂肪族 C-H 键转化为肟醚的策略。在该策略中，十钨酸根阴离子和硫酸根在从烷烃的一级、二级和三级 C-H 键中提取氢原子方面发挥互补作用。烷烃易于获得，底物范围广，条件温和，这些反应具有出色的区域选择性，使该策略适用于将原材料转化为高价值化学品。
• Facile Synthesis of Cyclic Dipeptides and Detection of Racemization
  作者：Toshihisa Ueda、Morinobu Saito、Tetsuo Kato、Nobuo Izumiya

  DOI：10.1246/bcsj.56.568

  日期：1983.2

  Several cyclic dipeptides were synthesized by refluxing methanolic solution of dipeptide methyl esters in high yield and purity. Cyclic dipeptides prepared by the Fischer method, the Nitecki method, and the present methanol-reflux method were compared with respect to yield and optical purity. The methanol-reflux method usually gave good results. High-performance liquid chromatography was effectively applied to detect racemization.

  通过回流二肽甲酯的甲醇溶液，合成了几个高产率和高纯度的环状二肽。通过Fischer法、Nitecki法和当前的甲醇回流法准备的环状二肽，在产率和光学纯度方面进行了比较。甲醇回流法通常能得到良好的结果。高效液相色谱法有效地应用于检测外消旋化。
• Synthesis and Antitumor Activity of Amino Acid Ester Derivatives Containing 5-Fluorouracil
  作者：Jing Xiong、Hai-Feng Zhu、Ya-Juan Zhao、Yun-Jun Lan、Ji-Wang Jiang、Jing-Jing Yang、Shu-Feng Zhang

  DOI：10.3390/molecules14093142

  日期：——

  A series of amino acid ester derivatives containing 5-fluorouracil were synthesized using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N-hydroxybenzotriazole (HOBt) as a coupling agent. The structures of the products were assigned by NMR, MS, IR etc. The in vitro antitumor activity tests against leukaemia HL-60 and liver cancer BEL-7402 indicated that (R)-ethyl 2-(2-(5-fluoro-2

  以1-乙基-3-(3-二甲基氨基丙基)碳二亚胺盐酸盐(EDC·HCl)和N-羟基苯并三唑(HOBt)为偶联剂合成了一系列含5-氟尿嘧啶的氨基酸酯衍生物。产物的结构经NMR、MS、IR等鉴定。体外对白血病HL-60和肝癌BEL-7402的抗肿瘤活性试验表明(R)-乙基2-(2-(5-氟-2 ,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)-3-(4-hydroxyphenyl)propanoate 对 BEL-7402 的抑制作用比 5-FU 更强。
• Stereoselective alkylation of chiral glycine enolate synthons. The enantioselective synthesis of α-amino acid derivatives.
  作者：Joseph F. Dellaria、D.Santarsiero Bernard

  DOI：10.1016/s0040-4039(00)82269-8

  日期：——

  The highly stereoselective alkylation (% de=99.6 to 97.6) of a new chiral glycine enolate synthon derived from D-2-phenylglycinol is described. Deprotection of the alkylation adducts in a one-pot three-step procedure provides the ethyl ester hydrochloride salts of the corresponding α-amino acids with no attending racemization.

  描述了衍生自D-2-苯基甘氨醇的新的手性甘氨酸烯醇式合成子的高度立体选择性烷基化（％de = 99.6至97.6）。用一锅三步法对烷基化加合物进行脱保护，即可得到相应的α-氨基酸的乙酯盐酸盐，而不会发生外消旋作用。
• Tandem four-component reaction for efficient synthesis of dihydrothiophene with substituted amino acid ethyl esters
  作者：Jing Sun、Yu Zhang、Chao-Guo Yan

  DOI：10.1039/c8ra03605e

  日期：——

  The one-pot four-component reaction of aromatic aldehydes, malononitrile, 1,3-thiazolidinedione and ethyl glycinate hydrochloride in ethanol in the presence of triethylamine afforded trans-dihydrothiophene ureidoformamide derivatives in moderate to good yields. The other α-amino acid ethyl esters resulted in the corresponding diastereoisomeric dihydrothiophene derivatives with various molecular ratios

  在三乙胺存在下，芳香醛、丙二腈、1,3-噻唑烷二酮和甘氨酸乙酯盐酸盐在乙醇中的一锅四组分反应以中等至良好的产率提供反式-二氢噻吩脲基甲酰胺衍生物。其他α-氨基酸乙酯产生具有不同分子比的相应非对映异构二氢噻吩衍生物。通过与DDQ的连续脱氢反应也成功地制备了官能化噻吩衍生物。