1,1,2-肼三羧酸三叔丁酯 | 185456-26-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1,1,2-肼三羧酸三叔丁酯
• 中文别名: BOC3-肼
• 英文名称: tri-tert-butyl hydrazine-1,1,2-tricarboxylate
• 英文别名: tri(tert-butoxycarbonyl)hydrazine；tri-tert-butoxycarbonylhydrazine；1,1,2-Boc₃-hydrazine；1,1,2-triBochydrazine；tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbamate
• CAS: 185456-26-2
• 化学式: C₁₅H₂₈N₂O₆
• 分子量: 332.397
• InChiKey: XDILSMVBIXONSC-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2928000090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，密封，干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Tris-(t-butyloxycarbonyl)-hydrazine
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: Tris-(t-butyloxycarbonyl)-hydrazine
CAS number: 185456-26-2

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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, refrigerated.
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: C15H28N2O6
Molecular weight: 332.4

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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：

  1,1,2-肼三羧酸三叔丁酯 在 二氯二茂钛 锰 、 2,4,6-collidine hydrochloride 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 77.0h， 生成
  参考文献：
  名称：

  Cu-Catalysed N-Arylation of Hydrazines with Bismuthanes: Synthesis and Pinacol or Imino-Pinacol Coupling of 4-Formylphenylhydrazines and their Phenylimine Derivatives

  摘要：

  制备了受乙缩醛保护的 4-甲酰基苯基铋烷，并将其用于三取代肼的芳基化反应。去除缩醛基团后得到的甲酰基苯肼在偶联反应中生成含有两个取代肼基的二元醇，而相应的苯基亚胺衍生物在偶联反应中生成相应的二元胺。

  DOI：

  10.1055/s-2004-835621
• 作为产物：
  描述：

  Hydrazinetetracarboxylic acid, tris(1,1-dimethylethyl) phenylmethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 1,1,2-肼三羧酸三叔丁酯
  参考文献：
  名称：

  Maeeorg, Uno; Grehn, Leif; Ragnarsson, Ulf, Angewandte Chemie, 1996, vol. 108, # 22, p. 2802 - 2803

  摘要：

  DOI：

文献信息

• Addition of Arylboronic Acids to Symmetrical and Unsymmetrical Azo Compounds
  作者：Ksenija Kisseljova、Olga Tšubrik、Rannar Sillard、Sirje Mäeorg、Uno Mäeorg

  DOI：10.1021/ol052403f

  日期：2006.1.1

  [reaction: see text] The addition of aryl- and heteroarylboronic acids to azo compounds is described. Copper salt catalysis was necessary to perform the reaction under mild conditions and high yields. Excellent regioselectivity was observed in addition to unsymmetrical azo compounds.

  [反应：见正文]描述了向偶氮化合物中添加芳基硼酸和杂芳基硼酸。铜盐催化对于在温和的条件下以高收率进行反应是必要的。除了不对称的偶氮化合物外，还观察到了优异的区域选择性。
• Improvements to the Synthesis of Isofagomine, Noeuromycin, Azafagomine, and Isofagomine Lactam, and a Synthesis of Azanoeuromycin and 'Guanidine' Isofagomine
  作者：Peter J. Meloncelli、Robert V. Stick

  DOI：10.1071/ch06241

  日期：——

  Improvements in the preparation of a key imidazylate and the reduction of the derived nitrile have led to more efficient syntheses of isofagomine, noeuromycin, azafagomine, and isofagomine lactam. As well, a precursor of azafagomine has been converted into azanoeuromycin, and the nitrogen atom of isofagomine has been incorporated into a guanidine residue.

  通过改进关键咪唑盐酸盐的制备和衍生腈的还原，可以更有效地合成异法哥明、新霉素、氮法哥明和异法哥明内酰胺。此外，氮杂阿戈明的一种前体已转化为氮杂新霉素，而异阿戈明的氮原子已与胍残基结合。
• [EN] 1 H-PYRAZOL-1 -YL-THIAZOLES AS INHIBITORS OF LACTATE DEHYDROGENASE AND METHODS OF USE THEREOF<br/>[FR] 1 H-PYRAZOLE-1 -YL-THIAZOLES COMME INHIBITEURS DE LACTATE DÉSHYDROGÉNASE ET PROCÉDÉS DE LEURS UTILISATIONS
  申请人：US HEALTH

  公开号：WO2018005807A1

  公开（公告）日：2018-01-04

  The disclosure provides a compound of the formula (II) and pharmaceutically acceptable salts thereof. The variables, e.g. n, R, R3, R10, X, Y, and Z are defined herein. These compounds act as lactate dehydrogenase inhibitors and are useful for treating cancer and fibrosis. The compounds may be particularly useful for treating forms of cancer in which a metabolic switch from oxidative phosphorylation to glycolysis has occurred. The disclosure also provides pharmaceutical compositions containing a compound of this formula and method for treating patients having cancer, fibrosis, or other conditions in which a metabolic switch from oxidative phosphorylation to glycolysis has occurred.

  该披露提供了公式（II）的化合物及其药用盐。变量，例如n、R、R3、R10、X、Y和Z在此处有定义。这些化合物作为乳酸脱氢酶抑制剂，并且适用于治疗癌症和纤维化。这些化合物可能特别适用于治疗那些发生了代谢从氧化磷酸化转变为糖酵解的癌症形式。该披露还提供了含有该公式化合物的药物组合物，以及治疗患有癌症、纤维化或其他发生了代谢从氧化磷酸化转变为糖酵解的病情的患者的方法。
• Synthesis of Hydrazines with Aromatic Substituents Using Triarylbismuth Reagents
  作者：Olavi Loog、Uno Mäeorg、Ulf Ragnarsson

  DOI：10.1055/s-2000-7600

  日期：——

  Smooth monoarylation of two triprotected hydrazine reagents under mild conditions has been accomplished using triarylbismuthanes in the presence of copper acetate and amine to give products 3 and 6 in excellent yield. Arylation on N 2 after selective deprotection of derivatives with alkyl or aryl substituents on N 1, resulting in compounds 8 and 9, is also demonstrated. Furthermore, other products derived from these reagents with free N-alkyl and N-aryl functions undergo the same reaction to give substances such as 10 and 11. As a result, the scope of the original hydrazine reagents has been further extended. A few reference compounds have also been prepared directly from phenylhydrazine.

  在温和的条件下，使用三芳基铋烷在醋酸铜和胺的存在下完成了两种三保护肼试剂的平滑单芳基化反应，得到了产率极高的产物 3 和 6。在对 N 1 上带有烷基或芳基取代基的衍生物进行选择性脱保护后，N 2 上的芳基化反应也得到了化合物 8 和 9。此外，由这些试剂衍生出的具有游离 N-烷基和 N-芳基官能团的其他产物也会发生同样的反应，生成 10 和 11 等物质。因此，原始肼试剂的应用范围得到了进一步扩展。一些参考化合物也是直接从苯肼中制备出来的。
• Arylation of diversely substituted hydrazines by tri- and pentavalent organobismuth reagents
  作者：Olga Tšubrik、Uno Mäeorg、Rannar Sillard、Ulf Ragnarsson

  DOI：10.1016/j.tet.2004.07.020

  日期：2004.9

  hydrazides to triply protected hydrazines and included a large number of intermediates of principal synthetic interest. In the case of mono- and disubstituted hydrazines the results demonstrate apparent advantages of pentavalent over trivalent reagents, exemplified by fast, highly chemoselective monoarylation of acylhydrazines at the terminal nitrogen. In contrast, trisubstituted hydrazines are more efficiently

  在三芳基铋和三芳基铋二乙酸盐试剂的芳基化方面，研究了各种肼衍生物，重点是范围和局限性。在这些试剂中，有一些在其芳环中含有庞大的取代基。所施加的底物涵盖从简单的酰肼到三重保护的肼的范围，并且包括大量具有主要合成意义的中间体。在单取代和二取代的肼的情况下，结果表明五价取代三价试剂的明显优势，例如末端氮原子上快速，高度化学选择性的酰肼单芳基化。相反，三取代肼更有效地被三价试剂取代。对于这些底物，偶尔会观察到空间因素的强烈影响，反映在较低的收率甚至完全抑制反应上。使用逐步或一锅法将两个不同的芳族取代基引入二取代的肼中。