二甲基-3,3’-联砒啶-5,5’-二羧酸 | 128612-43-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 二甲基-3,3’-联砒啶-5,5’-二羧酸
• 中文别名: 二甲基-3,3'-联砒啶-5,5'-二羧酸
• 英文名称: 5,5'-Bis(methoxycarbonyl)-3,3'-bipyridine
• 英文别名: dimethyl 3,3'-bipyridyl-5,5'-dicarboxylate；[3,3']bipyridinyl-5,5'-dicarboxylate；dimethyl (3,3′-bipyridine)-5,5′-dicarboxylate；Dimethyl [3,3'-bipyridine]-5,5'-dicarboxylate；methyl 5-(5-methoxycarbonylpyridin-3-yl)pyridine-3-carboxylate
• CAS: 128612-43-1
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: FHLQRZZILYBCDV-UHFFFAOYSA-N

物化性质

• 熔点：
  226-230
• 沸点：
  443.1±45.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Dimethyl 3,3’-bipyridine-5,5’-dicarboxylate
Synonyms: Methyl 5-[5-(methoxycarbonyl)pyridin-3-yl]nicotinate

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Dimethyl 3,3’-bipyridine-5,5’-dicarboxylate
CAS number: 128612-43-1

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C14H12N2O4
Molecular weight: 272.3

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二甲基-3,3’-联砒啶-5,5’-二羧酸 在 甲醇 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以95.7%的产率得到3,3'-联吡啶]-5,5'-二羧酸
  参考文献：
  名称：

  由交联螺旋链构建的微孔 MOF 用于高效纯化天然气和乙烯

  摘要：

  天然气 (NG) 和乙烯 (C 2 H 4 ) 是两种对制造多功能精细化学品和/或聚合物具有重要价值的原材料，因此开发了固体吸附剂，如金属有机骨架 (MOF) 应用于其净化非常关键，但仍然极具挑战性。在这项研究中，我们设计并合成了一种含有混合 N 和 O 配位供体的配体，该配体与 Cu(II) 离子进行溶剂热组装以生成微孔 MOF。X 射线晶体学显示，标题 MOF 包含一维 (1D) 同手性螺旋链，这些螺旋链在三周期配位框架中进行了交联以形成开放通道。此外，C 1 –C 2的行为对吸附在标题 MOF 中的碳氢化合物和二氧化碳 (CO 2 ) 进行了系统研究，揭示了其在纯化 NG 和 C 2 H 4 方面的潜力。在 109 kPa 和 298 K 下，C 2 /甲烷 (CH 4 )、CO 2 /CH 4和乙炔 (C 2 H 2 )/C 2 H 4吸附选择性令人印象深刻，分别高达 62.9、28

  DOI：

  10.1021/acs.inorgchem.1c02363
• 作为产物：
  描述：

  5-溴烟酸甲酯 在 dibromobis(triphenylphosphine)nickel(II) 、 四乙基碘化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以73%的产率得到二甲基-3,3’-联砒啶-5,5’-二羧酸
  参考文献：
  名称：

  Homocoupling of Aryl Halides Using Nickel(II) Complex and Zinc in the Presence of Et₄NI. An Efficient Method for the Synthesis of Biaryls and Bipyridines

  摘要：

  在乙基四氟铵存在下，用锌还原NiX2(PPh3)2可以得到一种镍催化剂，该催化剂已被证明对芳基卤化物的偶联反应非常有效。此镍催化剂可以在THF中制备，无需额外的三苯基磷，并且对芳基氯、溴和碘的同类偶联反应有效，以良好的产率生成双芳烃和双吡啶。所报道的新方法提供了一种简单的方法，用于获得双芳烃和双吡啶的新型衍生物。

  DOI：

  10.1246/bcsj.63.80

文献信息

• A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates
  作者：Kai Kang、Nathan L. Loud、Tarah A. DiBenedetto、Daniel J. Weix

  DOI：10.1021/jacs.1c10907

  日期：2021.12.29

  medicine and materials science, the synthesis of biheteroaryls by cross-coupling remains challenging. We describe here a new, general approach to biheteroaryls: the Ni- and Pd-catalyzed multimetallic cross-Ullmann coupling of heteroaryl halides with triflates. An array of 5-membered, 6-membered, and fused heteroaryl bromides and chlorides, as well as aryl triflates derived from heterocyclic phenols,

  尽管它们对医学和材料科学很重要，但通过交叉偶联合成双杂芳基仍然具有挑战性。我们在这里描述了一种新的、通用的双杂芳基方法：杂芳基卤化物与三氟甲磺酸酯的 Ni 和 Pd 催化的多金属交叉 Ullmann 偶联。一系列 5 元、6 元和稠合杂芳基溴化物和氯化物，以及衍生自杂环酚的芳基三氟甲磺酸酯，被证明是该反应中可行的底物（62 个示例，平均产率为 63 ± 17%）。这种方法对双杂芳基的普遍性在 10 μmol 规模的 96 孔板格式中得到进一步证明。一组 96 种可能的产品在一组条件下提供了 >90% 的命中率。此外，可以使用配体、添加剂和还原剂的单个“工具箱板”快速优化低产率组合。
• [EN] HYDROXAMIC ACID DERIVATIVES AS GRAM-NEGATIVE ANTIBACTERIAL AGENTS<br/>[FR] DÉRIVÉS DE L'ACIDE HYDROXAMIQUE EN TANT QU'AGENTS CONTRE DES BACTÉRIES À GRAM NÉGATIF
  申请人：ASTRAZENECA AB

  公开号：WO2010100475A1

  公开（公告）日：2010-09-10

  The invention relates to chemical compounds of formula (IB): or a salt thereof. In some embodiments, the invention relates to inhibitors of UDP-3-0 — (R-S-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC). In still further embodiments, the invention relates to pharmaceutical compositions comprising compounds disclosed herein and their use in the prevention and/or treatment of Gram- negative bacterial infections.

  该发明涉及化学式(IB)的化合物或其盐。在某些实施例中，该发明涉及UDP-3-0-(R-S-羟基肉豆蔻酰)-N-乙酰葡萄糖胺脱乙酰酶(LpxC)的抑制剂。在更进一步的实施例中，该发明涉及包含本文披露的化合物的药物组合物及其在预防和/或治疗革兰氏阴性细菌感染中的用途。
• Homocoupling of Aryl Halides Using Nickel(II) Complex and Zinc in the Presence of Et₄NI. An Efficient Method for the Synthesis of Biaryls and Bipyridines
  作者：Masahiko Iyoda、Hiroki Otsuka、Koichi Sato、Nobue Nisato、Masaji Oda

  DOI：10.1246/bcsj.63.80

  日期：1990.1

  Reduction of NiX2(PPh3)2 with zinc in the presence of Et4NI gives a nickel catalyst which has been proven to be useful for the coupling of aryl halides. This nickel catalyst can be prepared in THF without an additional triphenylphosphine and is effective for the homocoupling of aryl chlorides, bromides, and iodides to produce biaryls and bipyridines in good yields. The reported new approach provides a simple access to novel derivatives of biaryls and bipyridines.

  在乙基四氟铵存在下，用锌还原NiX2(PPh3)2可以得到一种镍催化剂，该催化剂已被证明对芳基卤化物的偶联反应非常有效。此镍催化剂可以在THF中制备，无需额外的三苯基磷，并且对芳基氯、溴和碘的同类偶联反应有效，以良好的产率生成双芳烃和双吡啶。所报道的新方法提供了一种简单的方法，用于获得双芳烃和双吡啶的新型衍生物。
• Total Synthesis of (±)-Cytisine
  作者：Brian T. O'Neill、Daniel Yohannes、Mark W. Bundesmann、Eric P. Arnold

  DOI：10.1021/ol0067538

  日期：2000.12.1

  benzylation and then reduction of a pyridinium ring. The penultimate diazabicyclo[3.3.1]nonane intermediate was obtained with high diastereoselectivity. A similar sequence has been employed for the synthesis of novel derivative 9-methoxycytisine.

  [反应：见正文]尼古丁部分激动剂胱氨酸是通过五个步骤制备的，其特征是“原位” Stille或铃木联芳基吡啶偶联。吡啶环的分化是通过选择性苄基化然后还原吡啶环来实现的。以高非对映选择性获得倒数第二个二氮杂双环[3.3.1]壬烷中间体。类似的序列已用于合成新的衍生物9-甲氧胞苷。
• IYODA, MASAHIKO;OTSUKA, HIROKI;SATO, KOICHI;NISATO, NOBUE;ODA, MASAJI, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 80-87
  作者：IYODA, MASAHIKO、OTSUKA, HIROKI、SATO, KOICHI、NISATO, NOBUE、ODA, MASAJI

  DOI：——

  日期：——