(R)-2-羟基-4-甲基戊酸 | 20312-37-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (R)-2-羟基-4-甲基戊酸
• 英文名称: (R)-2-hydroxy-4-methylpentanoic acid
• 英文别名: D-leucic acid；(R)-(+)-leucic acid；D-2-hydroxyisocaproic acid；(R)-leucinic acid；D-α-hydroxyisocaproic acid；(R)-2-hydroxyisocaproic acid；D-O-leucine；(2R)-2-hydroxy-4-methylpentanoic acid
• CAS: 20312-37-2
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: LVRFTAZAXQPQHI-RXMQYKEDSA-N

物化性质

• 熔点：
  76-80℃
• 沸点：
  251.3±13.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜
• LogP：
  0.522 (est)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090
• WGK Germany：
  3
• 储存条件：
  存放于室温、干燥且密封的环境中

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (R)-2-Hydroxy-4-methylpentanoic acid
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: (R)-2-Hydroxy-4-methylpentanoic acid
CAS number: 20312-37-2

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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: C6H12O3
Molecular weight: 132.2

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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.

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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

(S)-Leuacic 酸是一种氨基酸代谢物，具有生物活性。

反应信息

• 作为反应物：
  描述：

  (R)-2-羟基-4-甲基戊酸 在 硫酸 、 叔丁基锂 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 21.5h， 生成 (R)-4-hydroxy-2,6-dimethylhept-1-en-3-one
  参考文献：
  名称：

  通过有机催化共轭添加α-氰基乙酸酯到甲基丙烯酸甲酯上的全碳叔/季不相邻立体中心的不对称组装

  摘要：

  基于布朗斯台德碱催化的迈克尔加成/α-质子化序列，涉及α-氰基乙酸酯和2,4-二甲基-4-基羟基戊烯-3-一作为新的甲基丙烯酸酯等同物。

  DOI：

  10.1002/chem.201603082
• 作为产物：
  描述：

  DL-亮氨酸 以 水 为溶剂， 以73%的产率得到(R)-2-羟基-4-甲基戊酸
  参考文献：
  名称：

  圆偏振同步辐射在冰中rac-亮氨酸的光反应：温度诱导机理从诺里斯II型转变为脱氨基

  摘要：

  认为外星有机物向原始地球的输送触发了生命的起源和随后的进化。实际上，已经在碳质陨石中发现了非陆地来源的对映异构体富集的氨基酸，并且有人提出在外层空间中通过圆偏振光（CPL）进行对映体选择性光分解在初始对映体偏斜中起了一定作用。为了通过实验检验这种可能性并阐明光反应机理，我们研究了左旋和右旋CPL在21–298 K的酸性和中性冰/水介质中消旋亮氨酸（rac -Leu）的光解，以尝试对映体检测富集的D-和L‐Leu，分别。全面的产品分析表明，即使在21 K时，CPL诱导的Leu消酸作用在酸性和中性冰基质中均会发生，并且其主要机理是在降低温度时从Norrish II型γ氢提取转变为S N i脱氨。讨论了CPL诱导的氨基酸光分解作为陨石中对映异构体失衡的潜在作用。

  DOI：

  10.1002/chem.201301831

文献信息

• Enantioselective synthesis of α-hydroxy carboxylic acids: Direct conversion of α-oxocarboxylic acids to enantiomerically enriched α-hydroxy carboxylic acids via neighboring group control
  作者：Zhe Wang、Brittany La、Joseph M. Fortunak、Xian-Jun Meng、George W. Kabalka

  DOI：10.1016/s0040-4039(98)01162-9

  日期：1998.7

  α-Oxocarboxylic acids can be reduced to the corresponding α-hydroxy carboxylic acids employing DIP-C1tm as a reducing agent. The α-carboxylic substituent exerts a remarkable neighboring group effect on the reduction. The reaction presumably proceeds in an intramolecular fashion through a “rigid” bicyclic transition state assembly, which produces enantioselectivities approaching 99%.

  可以使用DIP-C1 tm作为还原剂将α-氧代羧酸还原为相应的α-羟基羧酸。α-羧基取代基对还原反应具有显着的邻近基团效应。该反应大概通过“刚性”双环过渡态组装体以分子内方式进行，其产生接近99％的对映选择性。
• Azacyclosteroid histamine-3 receptor ligands
  申请人：Zhao Chen

  公开号：US20050227953A1

  公开（公告）日：2005-10-13

  Azacyclosteroid histamine-3 receptor ligands, pharmaceutical compositions comprising such compounds, and methods for using such compounds and compositions are described herein.

  阿扎环状类固醇组胺-3受体配体、包含该化合物的药物组合物以及使用这些化合物和组合物的方法在本文件中进行了描述。
• Siamese Depsipeptides: Constrained Bicyclic Architectures
  作者：Javier Ruiz-Rodríguez、Jan Spengler、Fernando Albericio

  DOI：10.1002/anie.200904135

  日期：2009.10.26

  The first members of a new class of depsipeptides with tartaric acid as the core unit, called Siamese depsipeptides, are described. These compounds were synthesized from a branched precursor in only one cyclization step. The structural manipulation of a natural bioactive depsipeptide (sansalvamide A) gives analogues with greater activity, and thereby provides additional information on structure–activity

  描述了以酒石酸为核心单元的新型二肽肽的第一成员，称为暹罗二肽。这些化合物仅在一个环化步骤中就由支链前体合成。天然生物活性二肽（sansalvamide A）的结构操作使类似物具有更高的活性，从而提供了结构-活性关系的更多信息（请参见结构）。
• [EN] MODULATORS OF THE G PROTEIN-COUPLED MAS RECEPTOR AND THE TREATMENT OF DISORDERS RELATED THERETO<br/>[FR] MODULATEURS POUR LE RÉCEPTEUR MAS COUPLÉ À LA PROTÉINE G ET TRAITEMENT DES TROUBLES QUI Y SONT APPARENTÉS
  申请人：ARENA PHARM INC

  公开号：WO2013070657A1

  公开（公告）日：2013-05-16

  The present invention relates to compounds of Formula (I) and pharmaceutically acceptable salts, solvates, and hydrates thereof that are useful in methods of treatment and alleviation of diseases and disorders of the heart, brain, kidney, immune, and reproductive system resulting from ischemia, or reperfusion subsequent to ischemia, and any downstream complication(s) related thereto. The present invention further relates to methods of treatment and alleviation of diseases and disorders of the vasculature resulting from vasoconstriction or hypertension and any downstream complication(s) resulting from elevated blood pressure and/or reduced tissue perfusion.

  本发明涉及式（I）化合物及其药用可接受的盐、溶剂和水合物，这些化合物在治疗和缓解由缺血引起的心脏、脑、肾脏、免疫系统和生殖系统的疾病和紊乱方面具有用处，或者在缺血后再灌注引起的疾病和障碍，以及与之相关的任何下游并发症。本发明还涉及治疗和缓解由血管收缩或高血压引起的血管疾病和障碍的方法，以及由高血压和/或组织灌注减少引起的任何下游并发症。
• [EN] SUBSTITUTED PYRAZOLO[1,5-A]PYRIDINE COMPOUNDS AS RET KINASE INHIBITORS<br/>[FR] COMPOSÉS SUBSTITUÉS DE PYRAZOLO[1,5-A]PYRIDINES COMME INHIBITEURS DE LA KINASE RET
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2017011776A1

  公开（公告）日：2017-01-19

  Provided herein are compounds of the General Formula I: and stereoisomers and pharmaceutically acceptable salts or solvates thereof, in which A, B, D, E, X1, X2, X3 and X4 have the meanings given in the specification, which are inhibitors of RET kinase and are useful in the treatment and prevention of diseases which can be treated with a RET kinase inhibitor, including diseases or disorders mediated by a RET kinase.

  本文提供了一般式I的化合物及其立体异构体和药用可接受的盐或溶剂，其中A、B、D、E、X1、X2、X3和X4的含义如规范中所述，这些化合物是RET激酶的抑制剂，可用于治疗和预防可以用RET激酶抑制剂治疗的疾病，包括由RET激酶介导的疾病或紊乱。