3-(Fmoc-氨基)-1-丙醇 | 157887-82-6

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 3-(Fmoc-氨基)-1-丙醇
• 中文别名: 3-(FMOC-氨基)-1-丙醇
• 英文名称: 9H-fluoren-9-ylmethyl N-(3-hydroxypropyl)carbamate
• 英文别名: (9H-fluoren-9-yl)methyl (3-hydroxypropyl)carbamate；Fmoc-3-amino-1-propanol；3-(FMOC-amino)-1-propanol；3-Fmoc-amino-propan-1-ol；Fmoc-beta-alaninol
• CAS: 157887-82-6
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: GNXZNUJDAMSJFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126
• 沸点：
  518.9±33.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）
• 稳定性/保质期：
  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封储存，存放在阴凉干燥的仓库中，并需防潮。通常采用惰性气体进行保护。冷藏时温度应控制在2-8℃。

SDS

Name:	9H-fluoren-9-ylmethyl n-(3-hydroxypropyl)carbamate 97% Material Safety Data Sheet
Synonym:
CAS:	157887-82-6

Section 1 - Chemical Product MSDS Name:9H-fluoren-9-ylmethyl n-(3-hydroxypropyl)carbamate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
157887-82-6	9H-Fluoren-9-ylmethyl N-(3-hydroxyprop	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Moisture sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Keep refrigerated. (Store below 4C/39F.) Store in a tightly closed container. Store in a dry area. Store under nitrogen. Store under argon.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 157887-82-6: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 124 - 126 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C18H19NO3
Molecular Weight: 297

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Oxidizing agents, acid chlorides, reducing agents, bases, amines.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 157887-82-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
9H-Fluoren-9-ylmethyl N-(3-hydroxypropyl)carbamate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 157887-82-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 157887-82-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 157887-82-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(Fmoc-氨基)-1-丙醇 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以85%的产率得到(9H-fluoren-9-yl)methyl (3-iodopropyl)carbamate
  参考文献：
  名称：

  Conjugation of a novel histidine derivative to biomolecules and labelling with [99mTc(OH2)3(CO)3]+Electronic supplementary information (ESI) available: complete 1H and 13C NMR spectra of 14, 15, 16 and 19. See http://www.rsc.org/suppdata/ob/b4/b405575f/

  摘要：

  新的组氨酸衍生物3-{1-[3-(9H-芴-9-基甲氧基羧酰氨基)-丙基]-1H-咪唑-4-基}-2-(3-三甲基硅基-乙基氨基羧酸)-丙酸甲酯（7）通过将组氨酸尿素衍生物(7S)-5,6,7,8-四氢-7-(甲氧基羧基)-5-氧代咪唑-[1,5-c]-嘧啶（2）与Fmoc保护的3-碘丙胺进行烷基化，然后使用2-三甲基硅基乙醇开环反应制备而成。在使用HNEt2去除Fmoc后，将组氨酸胺衍生物通过酰胺形成与生物素、五肽亮氨酸-脑啡肽以及维生素B12-β-酸偶联，采用TBTU作为耦合试剂。为了使组氨酸能够进行标记，teoc保护基团通过NBu4F（用于生物素偶联物）或TFA（用于脑啡肽和B12偶联物）去除。将10−4 M浓度的生物偶联物与[99mTc(H2O)3(CO)3]+在50 °C下反应30分钟，在每个情况下HPLC放射色谱图中产生一个单一的新峰，确认了相应生物分子的定量标记。为了评估标记化合物的性质，还合成了与Re(CO)3的铼类似物，类似的滞留时间确认了与99mTc标记偶联物的身份。

  DOI：

  10.1039/b405575f
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 3-氨基-1-丙醇 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 3-(Fmoc-氨基)-1-丙醇
  参考文献：
  名称：

  New Nonnucleoside Substrates for Terminal Deoxynucleotidyl Transferase: Synthesis and Dependence of Substrate Properties on Structure

  摘要：

  合成了三种化合物：N-(9-芴甲氧羰基)-ω-氨基烷基-, N-(9-芴甲氧羰基)-8-氨基-3,6-二氧杂辛基-, 和 N-[(9-芴甲氧羰基)-6-氨基己酰基]-2-氨基乙基三磷酸盐。所有这些化合物都被证明是牛胸腺末端脱氧核苷酸转移酶的底物。它们的底物性质取决于连接9-芴甲氧羰基和三磷酸基团之间链的长度和结构。

  DOI：

  10.1007/s11171-005-0048-y

文献信息

• ANTI-EGFR ANTIBODY DRUG CONJUGATES
  申请人：AbbVie Inc.

  公开号：US20190153107A1

  公开（公告）日：2019-05-23

  The invention relates to anti-Epidermal Growth Factor Receptor (EGFR) antibody drug conjugates (ADCs) which inhibit Bcl-xL, including compositions and methods of using said ADCs.

  这项发明涉及抑制Bcl-xL的抗表皮生长因子受体（EGFR）抗体药物结合物（ADCs），包括使用所述ADCs的组合物和方法。
• Repetitive solid-phase synthesis of polyamines
  作者：Daniel Jönsson、Anders Undén

  DOI：10.1016/s0040-4039(02)00482-3

  日期：2002.4

  monoalkylated by acid labile, benzhydryl-based alkyl chlorides. Reductive alkylation of the resulting secondary amino group by Fmoc-protected aminoaldehydes gives a N-benzhydryl polyamine backbone. Treatment of the resin with trifluoroacetic acid cleaves both the benzhydryl protective group and the polyamine derivative from the resin. By using benzhydryl protective groups with different acid stability,

  描述了用于合成多胺的重复性固相方法。连接到交联的聚苯乙烯树脂上的伯氨基被酸不稳定的基于二苯甲基的烷基氯化物单烷基化。由Fmoc保护的氨基醛将所得仲氨基还原烷基化，得到N-苯甲酰基多胺主链。用三氟乙酸处理树脂可从树脂上裂解二苯甲基保护基和多胺衍生物。通过使用具有不同酸稳定性的二苯甲基保护基，可以合成无支链，支链和部分支链的多胺。
• Phosphine‐Catalyzed Synthesis of Chiral <i>N</i> ‐Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling
  作者：Charlotte Lorton、Nidal Saleh、Arnaud Voituriez

  DOI：10.1002/ejoc.202100404

  日期：2021.6.14

  Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1 H -pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.

  已经开发了膦催化的串联迈克尔加成/分子内Wittig反应用于合成手性2，5-二氢-1 H-吡咯和四氢吡啶衍生物。由于苯基硅烷原位还原了氧化膦，这些工艺在膦中变得具有催化作用。此外，使用对映纯手性膦进行催化和不对称P（III）/ P（V）过程。
• [EN] ANTIBODY DRUG CONJUGATES WITH CELL PERMEABLE BCL-XL INHIBITORS<br/>[FR] CONJUGUÉS ANTICORPS MÉDICAMENTS AVEC DES INHIBITEURS BCL-XL À PERMÉABILITÉ CELLULAIRE
  申请人：ABBVIE INC

  公开号：WO2016094505A1

  公开（公告）日：2016-06-16

  Small molecule Bcl-xL inhibitors and Antibody Drug Conjugates (ADCs) comprising small molecule Bcl-xL inhibitors are disclosed herein. The Bcl-xL inhibitors and ADCs of the disclosure are useful for, among other things, inhibiting anti-apoptotic Bcl xL proteins as a therapeutic approach towards the treatment of diseases that involve a dysregulated apoptosis pathway.

  本文披露了小分子Bcl-xL抑制剂和包含小分子Bcl-xL抑制剂的抗体药物结合物（ADCs）。本公开的Bcl-xL抑制剂和ADCs可用于抑制抗凋亡Bcl-xL蛋白，作为治疗涉及失调凋亡途径的疾病的治疗方法之一。
• [EN] PRODRUGS OF KETAMINE, COMPOSITIONS AND USES THEREOF<br/>[FR] PROMÉDICAMENTS À BASE DE KÉTAMINE, COMPOSITIONS ET UTILISATIONS DE CEUX-CI
  申请人：XW LAB INC

  公开号：WO2019137381A1

  公开（公告）日：2019-07-18

  Provided are prodrugs of (S) -or (R) -ketamine, including isotopically labeled ketamine,composition and uses thereof. Compounds having formula (Ia) or (Ib) as the prodrugs of (S) -or (R) -ketamine, including isotopically labeled ketamine, and pharmaceutical compositions comprising the compounds provided herein are used for treating or preventing a CNS disease.More particularly, the related diseases include depression and pain. (Ia) (Ib)

  提供了（S）-或（R）-氯胺酮的前药，包括同位素标记的氯胺酮，其组成和用途。具有化学式（Ia）或（Ib）的化合物作为（S）-或（R）-氯胺酮的前药，包括同位素标记的氯胺酮，以及包含本文提供的化合物的药物组合物用于治疗或预防中枢神经系统疾病。更具体地，相关疾病包括抑郁症和疼痛。（Ia）（Ib）