(4R)-4-羟基-L-脯氨酸盐酸盐 | 33996-30-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: (4R)-4-羟基-L-脯氨酸盐酸盐
• 中文别名: (2S,4R)-4-羟基吡咯烷-2-甲酸乙酯盐酸盐；4R-4-羟基-L-脯氨酸盐酸盐；L-4-羟脯氨酸乙酯盐酸盐
• 英文名称: trans-4-hydroxy-L-proline ethyl ester hydrochloride
• 英文别名: ethyl (2S,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride；Ethyl trans-4-hydroxy-L-prolinate hydrochloride；ethyl (2S,4R)-4-hydroxypyrrolidine-2-carboxylate;hydrochloride
• CAS: 33996-30-4
• 化学式: C₇H₁₃NO₃*ClH
• 分子量: 195.646
• InChiKey: HHXSZDXMSRXWJV-IBTYICNHSA-N

物化性质

• 熔点：
  150-153℃

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Hyp-OEt HCl
Synonyms: (2S,4R)-Ethyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride

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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-Hyp-OEt HCl
CAS number: 33996-30-4

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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: C7H13NO3.ClH
Molecular weight: 195.6

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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：

  (4R)-4-羟基-L-脯氨酸盐酸盐 在 4-二甲氨基吡啶 、 锂硼氢 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.5h， 生成 (2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin
  参考文献：
  名称：

  Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues

  摘要：

  Asymmetric syntheses of all four isomers of 4-amino-4-carboxyprolines, i.e. (2S,4S)-3, (2S,4R)-4, and their corresponding enantiomers, as novel conformationally restricted analogues of glutamic acid, were performed from trans-4-hydroxy-L-proline as a homochiral starting material. The key step was the spirohydantoin ring formation by employing the Bucherer-Bergs reaction of 4-oxoproline derivatives. These structures were determined by NMR studies.

  DOI：

  10.1016/0957-4166(95)00209-8
• 作为产物：
  描述：

  乙醇 、 L-羟基脯氨酸 在 氯化亚砜 作用下， 反应 18.0h， 以100%的产率得到(4R)-4-羟基-L-脯氨酸盐酸盐
  参考文献：
  名称：

  由4-羟基脯氨酸正式合成（+）-lactacystin

  摘要：

  使用非对映选择性烯酸酯酰化反应作为关键步骤，已由反式-4-羟基脯氨酸完成了（+）-lactacystin的正式合成。观察到非对映选择性随C4-O-保护基的空间体积而变化，并且与预期相反，当使用小的碳酸甲酯保护基时，获得了最佳的非对映选择性。然后通过拦截Shibasaki的路线，通过碳酸甲酯脱保护，脱水，3-吡咯啉至3-吡咯啉酮氧化，氢化和N -CO 2 Me脱保护，来完成正式合成。

  DOI：

  10.1016/j.tetlet.2012.10.076

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET PROCÉDÉS POUR LEUR UTILISATION
  申请人：SPINIFEX PHARM PTY LTD

  公开号：WO2013102242A1

  公开（公告）日：2013-07-11

  The present invention relates to heterocyclic compounds useful for antagonising angiotensin II Type 2 (AT2) receptor. More particularly the invention relates to pyrrolidine and azetidine compounds, compositions containing them and their use in methods of treating or preventing disorders or diseases associated with AT2 receptor function including neuropathic pain, inflammatory pain, conditions associated with neuronal hypersensitivity, impaired nerve conduction velocity, cell proliferation disorders, disorders associated with an imbalance between bone resorption and bone formation and disorders associated with aberrant nerve regeneration.

  本发明涉及用于拮抗血管紧张素II型2（AT2）受体的杂环化合物。更具体地，本发明涉及吡咯烷和氮杂环丙烷化合物，含有它们的组合物以及它们在治疗或预防与AT2受体功能相关的疾病或疾病的方法中的使用，包括神经病性疼痛、炎症性疼痛、与神经元过敏、神经传导速度受损、细胞增殖紊乱、骨吸收和骨形成之间失衡以及与异常神经再生相关的疾病。
• [EN] SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS<br/>[FR] COMPOSÉS DE SULFONAMIDE HÉTÉROCYCLIQUES SUBSTITUÉS UTILES COMME MODULATEURS DE TRPA1
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015052264A1

  公开（公告）日：2015-04-16

  The invention is concerned with the compounds of formula I or II: and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I or II as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

  本发明涉及式I或II的化合物及其盐。此外，本发明还涉及制备这些化合物的方法以及使用这些化合物的方法，以及含有这些化合物的药物组合物。这些化合物可能对治疗由TRPA1介导的疾病和状况，如疼痛，具有用途。
• Benzyl compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：Athena Neurosciences, Inc.

  公开号：US06362341B1

  公开（公告）日：2002-03-26

  Disclosed are compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, wherein the disease may be, for example, asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  揭示了结合VLA-4的化合物。其中某些化合物还抑制白细胞粘附，特别是通过VLA-4介导的白细胞粘附。这些化合物在治疗哺乳动物患者（例如人类）的炎症性疾病中很有用，例如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。
• Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone
  作者：Akiko Watanabe、Naotoshi Kiyota、Tetsuo Yamasaki、Kazuhiro Tanda、Tatsunori Miyagoe、Masanori Sakamoto、Masami Otsuka

  DOI：10.1002/jhet.627

  日期：2011.9

  isomers of the monomer of peptide nucleic acid (PNA) were derived from (2S,4R)‐4‐hydroxyproline; they had different stereochemistries at the C2 and C4 positions in the pyrrolidine ring. These different backbone conformations corresponding to four different stereochemistries were realized through a combination of inversions at the C2 and the C4 positions in pyrrolidine ring. The obtained backbone frameworks

  肽核酸（PNA）单体的四个异构体衍生自（2 S，4 R）-4-羟基脯氨酸; 它们在吡咯烷环的C 2和C 4位置具有不同的立体化学。通过组合在吡咯烷环中C 2和C 4位置上的转化，实现了与四个不同立体化学相对应的这些不同的主链构象。将获得的主链骨架与N-苯甲酰基胸腺嘧啶反应，得到相应的PNA单体。所得单体的光谱比较证实了其​​立体化学。J.杂环化​​学。（2011）。
• A heterogeneous layered bifunctional catalyst for the integration of aerobic oxidation and asymmetric C–C bond formation
  作者：Hiroyuki Miyamura、Gerald C. Y. Choo、Tomohiro Yasukawa、Woo-Jin Yoo、Shu Kobayashi

  DOI：10.1039/c3cc46204h

  日期：——

  The design and synthesis of a heterogeneous bifunctional chiral catalyst for the sequential aerobic oxidation–asymmetric Michael reactions between primary allylic alcohols and dibenzyl malonate are described. Interestingly, we found that layering bimetallic nanoparticles over the organocatalyst, within the chiral composite material, is crucial for catalytic activity.

  报道了用于一级烯丙醇与二苄基丙二酸酯顺序氧气氧化-不对称迈克尔反应的非均相双功能手性催化剂的设计与合成。有趣的是，我们发现将双金属纳米粒子层叠在手性复合材料中的有机催化剂上，对催化活性至关重要。