(alphaS)-1,3-二氢-alpha-(2-甲基丙基)-1,3-二氧代-2H-异吲哚-2-乙酸 | 2419-38-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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: (alphaS)-1,3-二氢-alpha-(2-甲基丙基)-1,3-二氧代-2H-异吲哚-2-乙酸
• 中文别名: 邻苯二甲酰亚胺-L-亮氨酸
• 英文名称: N-phthaloyl-(S)-leucine
• 英文别名: N-phthaloyl-L-leucine；(S)-2-(1,3-dioxoisoindolin-2-yl)-4-methylpentanoic acid；Phth-Leu-OH；N-phthalimide l-leucine；(2S)-2-(1,3-dioxoisoindolin-2-yl)-4-methylpentanoic acid；(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylpentanoic acid
• CAS: 2419-38-7
• 化学式: C₁₄H₁₅NO₄
• mdl: MFCD00065026
• 分子量: 261.277
• InChiKey: RMOSZIHTPMEZAP-NSHDSACASA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  426.4±28.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2925190090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Pht-Leu-OH
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: Pht-Leu-OH
CAS number: 2419-38-7

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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: C14H15NO4
Molecular weight: 261.3

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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.

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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：

  (alphaS)-1,3-二氢-alpha-(2-甲基丙基)-1,3-二氧代-2H-异吲哚-2-乙酸 生成 2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-4-甲基戊酸
  参考文献：
  名称：

  Reese, Justus Liebigs Annalen der Chemie, 1887, vol. 242, p. 1

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯二甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 (alphaS)-1,3-二氢-alpha-(2-甲基丙基)-1,3-二氧代-2H-异吲哚-2-乙酸
  参考文献：
  名称：

  环境自由基氧化剂NO 3 •对脂族氨基酸，二肽和三肽的氧化损伤：动力学和计算研究揭示酰胺键的作用

  摘要：

  动力学和计算数据表明，重要的环境自由基氧化剂NO 3 •在与脂肪族氨基酸以及二肽和三肽的反应中具有复杂的行为，这表明对肽主链中酰胺N–H键的攻击是高度可行的途径，这是通过质子耦合电子转移（PCET）机理进行的，在乙腈中的速率系数约为1×10 6 M –1 s –1。确定了类似的速率系数，用于确定侧链中α-碳和叔C–H键的夺氢作用。获得的NO 3 •反应速率系数带有脂族二肽和三肽的化合物表明，攻击在每个氨基酸残基的所有这些位点发生，这使得脂族肽序列极易受到NO 3 •诱导的氧化损伤的影响。NO 3 •与脂肪族肽中侧链的反应没有发现酰胺邻基效应的证据，酰胺邻基效应先前已发现可促进自由基诱导的苯丙氨酸侧链破坏。

  DOI：

  10.1021/acs.joc.8b03224
• 作为试剂：
  描述：

  1-(吡啶-2-基)-1H-吲哚 在 silver hexafluoroantimonate 、 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 palladium hydroxide 10 wt. % on activated carbon 、 甲酸铵 、 (alphaS)-1,3-二氢-alpha-(2-甲基丙基)-1,3-二氧代-2H-异吲哚-2-乙酸 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 32.5h， 生成 2-n-octyl-1H-indole
  参考文献：
  名称：

  通过切换C-H活化机理在钴（III）催化的C-H烷基化反应中的完全选择性控制

  摘要：

  基于氢芳基化的CH烷基化反应中的选择性控制主要受空间相互作用的影响。提出了一种概念上截然不同的策略，该策略利用钴催化利用了CH活化机理中的程序化开关，从而为与未活化烯烃的便捷CH烷基化奠定了基础。详细的机理研究为CH活化机制中的可编程转换提供了令人信服的证据，证明了从线性选择性配体到配体氢转移到分支选择性碱基辅助内部亲电子型取代的CH活化机制的转变。

  DOI：

  10.1002/anie.201704196

文献信息

• Electrochemical C(sp3)–H Fluorination
  作者：Yusuke Takahira、Miao Chen、Yu Kawamata、Pavel Mykhailiuk、Hugh Nakamura、Byron K. Peters、Solomon H. Reisberg、Chao Li、Longrui Chen、Tamaki Hoshikawa、Tomoyuki Shibuguchi、Phil S. Baran

  DOI：10.1055/s-0037-1611737

  日期：2019.6

  A simple and robust method for electrochemical alkyl C–H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C–H bonds are converted into their C–F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline.

  提出了一种简单而可靠的电化学烷基 C-H 氟化方法。使用简单的硝酸盐添加剂、广泛使用的氟源 (Selectfluor) 和碳基电极，各种活化和未活化的 C-H 键被转化为它们的 C-F 同系物。100 克氟缬氨酸制剂也证明了反应的可扩展性。
• Silver-Mediated Oxidative Aliphatic CH Trifluoromethylthiolation
  作者：Shuo Guo、Xiaofei Zhang、Pingping Tang

  DOI：10.1002/anie.201411807

  日期：2015.3.23

  of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver‐based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional‐group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural‐product

  未活化的脂族CH键直接进行实际的三氟甲硫基化反应的第一个例子是使用基于银的试剂。该反应操作简单，可扩展，并且在空气中的水性条件下进行。此外，通过将该方法应用于天然产物和天然产物衍生物的选择性三氟甲基硫醇化反应，证明了其广泛的范围和良好的官能团相容性。
• Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers
  作者：Yan Cai、Haihong Ge、Weize Sun、Zhiwei Miao

  DOI：10.1055/s-0034-1380384

  日期：2015.6

  The trifluoroborane-catalyzed C–H functionalization/S–H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

  三氟硼烷催化的α-重氮磷酸酯与硫醇的C-H官能化/S-H插入反应已经被开发出来。已经提出了一个合理的反应机理来理解这个复合反应。这个过程以中等到良好的产率和化学选择性提供了直接访问含有季铵中心的N,S-缩醛。
• Huperzine a prodrugs and uses thereof
  申请人：Pan Bai-Chuan

  公开号：US20070082922A1

  公开（公告）日：2007-04-12

  Disclosed are huperzine A prodrugs and method of synthesis thereof. The invention further relates to methods of treating, preventing or reversing neurodegenerative diseases, such as, Alzheimer's Disease and neuronal dysfunctions, such as, memory impairment using a pharmaceutical composition comprising a huperzine A prodrug as disclosed herein.

  揭示了Huperzine A 前药及其合成方法。本发明还涉及使用包含本文所述的 Huperzine A 前药的药物组合物治疗、预防或逆转神经退行性疾病，如阿尔茨海默病和神经功能障碍，如记忆障碍的方法。
• [EN] SMALL MOLECULES AGAINST CEREBLON TO ENHANCE EFFECTOR T CELL FUNCTION<br/>[FR] PETITES MOLÉCULES DIRIGÉES CONTRE LE CÉRÉBLON POUR AMÉLIORER LA FONCTION DES LYMPHOCYTES T EFFECTEURS
  申请人：H LEE MOFFITT CANCER CENTER & RES INST INC

  公开号：WO2017161119A1

  公开（公告）日：2017-09-21

  Disclosed are small molecules against cereblon to enhance effector T cell function. Methodos of making thes molecules and methods of using them to treat various disease states are also disclosed.

  披露了针对小脑蛋白以增强效应T细胞功能的小分子。还披露了制造这些分子的方法以及使用它们治疗各种疾病状态的方法。