N-[(苄氧基)羰基]-5-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-L-正缬氨酸 | 7767-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: N-[(苄氧基)羰基]-5-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-L-正缬氨酸
• 英文名称: Cbz-Orn(NPhth)-OH
• 英文别名: 2-benzyloxycarbonylamino-5-phthalimido-pentanoic acid；(S)-2-(((Benzyloxy)carbonyl)amino)-5-(1,3-dioxoisoindolin-2-yl)pentanoic acid；(2S)-5-(1,3-dioxoisoindol-2-yl)-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 7767-00-2
• 化学式: C₂₁H₂₀N₂O₆
• 分子量: 396.4
• InChiKey: QCLYZAIZBKHBFT-KRWDZBQOSA-N

物化性质

• 熔点：
  129-131 °C
• 沸点：
  643.2±55.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

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: Z-Orn(pht)-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: Z-Orn(pht)-oh
CAS number: 7767-00-2

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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: C21H20N2O6
Molecular weight: 396.4

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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：

  N-[(苄氧基)羰基]-5-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-L-正缬氨酸 在 camphor-10-sulfonic acid N-甲基吗啉 、 三乙基硅烷 、 氯甲酸乙酯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.25h， 生成 phenylmethyl [(1S)-1-(diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]methylcarbamate
  参考文献：
  名称：

  1,3-恶唑烷酮-5-酮和1,3-恶唑烷酮-6-酮由二十种常见的α-氨基酸合成N-甲基β-氨基酸的有效方法

  摘要：

  应用N-甲基β-氨基酸通常是潜在合成具有生物活性的修饰的肽和其他寡聚体的应用。先前的工作强调了1，3-恶唑烷-5-酮的还原裂解以合成N-甲基α-氨基酸。从α-氨基酸开始，使用两种方法来制备相应的N-甲基β-氨基酸。首先，α -氨基酸转化为Ñ甲基α -氨基酸由所谓的“-1,3-恶唑-5-酮的策略”，将它们再由同系阿恩特-艾斯特方法，得到Ñ-protected Ñ -甲基β -氨基酸选自20种常见衍生α -氨基酸。这些化合物的制备产率为23–57％（相对于N-甲基α-氨基酸）。在第二种方法中，可以通过Arndt–Eistert方法将12个N保护的α-氨基酸直接同源，然后将所得的β-氨基酸以30–45％的产率转化为1,3-恶二嗪-6-酮。 。最后，还原裂解以41–63％的收率提供了所需的N-甲基β-氨基酸。

  DOI：

  10.1002/hlca.200690235
• 作为产物：
  描述：

  N-methylsulfonylphthalimide 、 L-鸟氨酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-[(苄氧基)羰基]-5-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-L-正缬氨酸
  参考文献：
  名称：

  Melanocortin receptor-specific compounds

  摘要：

  一种具有结构I：1的一般式的黑素皮质素受体特异性化合物，其中X、R1、R2a、R2b、R3、R4a、R4b、R5a和R5b如说明书中所定义，该化合物与一个或多个黑素皮质素受体高亲和结合，并可选择性地为激动剂、拮抗剂、逆拮抗剂或逆拮抗剂的拮抗剂，并可用于治疗一个或多个黑素皮质素受体相关疾病或疾病，并且使用该发明化合物的方法。

  公开号：

  US20040224957A1

文献信息

• The effect of N-methylation on transition state mimetic inhibitors of the <i>Plasmodium</i> protease, plasmepsin V
  作者：Michelle Gazdik、Matthew T. O'Neill、Sash Lopaticki、Kym N. Lowes、Brian J. Smith、Alan F. Cowman、Justin A. Boddey、Brad E. Sleebs

  DOI：10.1039/c4md00409d

  日期：——

  An N-methylation strategy has been applied to transition state mimetics that are potent inhibitors of plasmepsin V to improve their physical characteristics and their ability to reduce the viability of Plasmodium parasites in culture.

  一种N-甲基化策略已应用于类似过渡态的模拟物，这些模拟物是强效的plasmepsin V抑制剂，以改善它们的物理特性和减少Plasmodium寄生虫在培养中的存活能力。
• PROCESSES AND INTERMEDIATE COMPOUNDS USEFUL FOR THE PREPARATION OF PLATELET GLYCOPROTEIN IIb/IIIa INHIBITORS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0699209A1

  公开（公告）日：1996-03-06
• [EN] PROCESSES AND INTERMEDIATE COMPOUNDS USEFUL FOR THE PREPARATION OF PLATELET GLYCOPROTEIN IIb/IIIa INHIBITORS<br/>[FR] PROCEDES ET COMPOSES INTERMEDIAIRES UTILES POUR LA PREPARATION D'INHIBITEURS PLAQUETTAIRES GLYCOPROTEIQUES IIb/IIIa
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1994026779A1

  公开（公告）日：1994-11-24

  (EN) This invention provides processes and intermediates for the synthesis of platelet glycoprotein IIb/IIIa inhibitors of formula (I).(FR) La présente invention décrit des procédés et des intermédiaires pour la synthèse d'inhibiteurs plaquettaires glycoprotéiques IIb/IIIa de formule (I).
• Effective Methods for the Synthesis ofN-Methylβ-Amino Acids from All Twenty Commonα-Amino Acids Using 1,3-Oxazolidin-5-ones and 1,3-Oxazinan-6-ones
  作者：Andrew B. Hughes、Brad E. Sleebs

  DOI：10.1002/hlca.200690235

  日期：2006.11

  N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to

  应用N-甲基β-氨基酸通常是潜在合成具有生物活性的修饰的肽和其他寡聚体的应用。先前的工作强调了1，3-恶唑烷-5-酮的还原裂解以合成N-甲基α-氨基酸。从α-氨基酸开始，使用两种方法来制备相应的N-甲基β-氨基酸。首先，α -氨基酸转化为Ñ甲基α -氨基酸由所谓的“-1,3-恶唑-5-酮的策略”，将它们再由同系阿恩特-艾斯特方法，得到Ñ-protected Ñ -甲基β -氨基酸选自20种常见衍生α -氨基酸。这些化合物的制备产率为23–57％（相对于N-甲基α-氨基酸）。在第二种方法中，可以通过Arndt–Eistert方法将12个N保护的α-氨基酸直接同源，然后将所得的β-氨基酸以30–45％的产率转化为1,3-恶二嗪-6-酮。 。最后，还原裂解以41–63％的收率提供了所需的N-甲基β-氨基酸。
• Melanocortin receptor-specific compounds
  申请人：Palatin Technologies, Inc.

  公开号：US20040224957A1

  公开（公告）日：2004-11-11

  A melanocortin receptor-specific compound of the general formula of structure I: 1 where X, R 1 , R 2a , R 2b , R 3 , R 4a , R 4b , R 5a and R 5b are as defined in the specification, which compound binds with high affinity to one or more melanocortin receptors and is optionally an agonist, an antagonist, an inverse agonist or an antagonist of an inverse agonist, and may be employed for treatment of one or melanocortin receptor-associated conditions or disorders, and methods for the use of the compounds of the invention.

  一种具有结构I：1的一般式的黑素皮质素受体特异性化合物，其中X、R1、R2a、R2b、R3、R4a、R4b、R5a和R5b如说明书中所定义，该化合物与一个或多个黑素皮质素受体高亲和结合，并可选择性地为激动剂、拮抗剂、逆拮抗剂或逆拮抗剂的拮抗剂，并可用于治疗一个或多个黑素皮质素受体相关疾病或疾病，并且使用该发明化合物的方法。