2-异氰基琥珀酸二甲酯 | 730964-72-4

• 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: 2-异氰基琥珀酸二甲酯
• 英文名称: dimethyl 2-isocyanosuccinate
• 英文别名: 2-Isocyanosuccinic acid dimethyl ester；dimethyl 2-isocyanobutanedioate
• CAS: 730964-72-4
• 化学式: C₇H₉NO₄
• mdl: MFCD04117552
• 分子量: 171.153
• InChiKey: ZMXWGHUWPDLSEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-异氰基琥珀酸二甲酯 在 水 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 生成 methyl 4-(2-methoxy-2-oxoethyl)-2-oxo-1,3-oxazinane-4-carboxylate
  参考文献：
  名称：

  Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water

  摘要：

  Reaction of alpha-substituted alpha-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

  DOI：

  10.1021/ja506031h
• 作为产物：
  描述：

  4-甲基DL-天冬氨酸氢酯 在 氯化亚砜 、 三乙胺 、 二异丙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 2-异氰基琥珀酸二甲酯
  参考文献：
  名称：

  Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water

  摘要：

  Reaction of alpha-substituted alpha-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

  DOI：

  10.1021/ja506031h

文献信息

• Carbon monoxide releasing molecules and uses thereof
  申请人：Blättler Walter Anton

  公开号：US09163044B2

  公开（公告）日：2015-10-20

  Provided herein are novel carbon-monoxide releasing molecules (CO-RMs) of the Formula (I): and esters, amides, salts, solvates and hydrates thereof; wherein R1 and R2 are as described herein. Also provided are pharmaceutical compositions comprising these compounds, methods of their preparation, and their use in the treatment of liver disease and inflammation.

  本文提供了一种新型的一氧化碳释放分子（CO-RMs），化学式为（I）：以及其酯、酰胺、盐、溶剂合物和水合物；其中R1和R2如本文所述。还提供了包含这些化合物的药物组合物、其制备方法，以及它们在肝病和炎症治疗中的用途。
• Integrated One-Pot Synthesis of 1,3-Oxazinan-2-ones from Isocyanoacetates and Phenyl Vinyl Selenones
  作者：Buyck, Thomas、Wang, Qian、Zhu, Jieping

  DOI：10.2533/chimia.2015.199

  日期：——

  Brønsted base (Et3N or DBU) catalyzed Michael addition of α-substituted α-isocyanoacetates to phenyl vinyl selenones followed by a Brønsted acid (PTSA) catalyzed domino oxidative cyclization afforded 1,3-oxazinan-2-ones in good to excellent yields. Enantio-enriched 1,3-oxazinan-2-ones were accessible using a Cinchona alkaloid-derived bifunctional catalyst for the first step. In this integrated one-pot process, the phenyl selenonyl group acted consecutively as an activator, a leaving group and a latent oxidant.

  Brønsted碱（Et3N或DBU）催化的α-取代α-异氰酸酯与苯基乙烯硒酮的Michael加成，然后经过Brønsted酸（PTSA）催化的多米诺氧化环化反应，产生了1,3-噁唑烷-2-酮，收率良好至优秀。通过使用Cinchona生物碱衍生的双功能催化剂作为第一步的手段，可制备对映富集的1,3-噁唑烷-2-酮。在这个一锅法过程中，苯基硒酰基依次作为活化剂、离去基和潜在氧化剂。
• New cleavable isocyanides for the combinatorial synthesis of α-amino acid analogue tetrazoles
  作者：Josef Mayer、Michael Umkehrer、Cédric Kalinski、Günther Ross、Jürgen Kolb、Christoph Burdack、Wolfgang Hiller

  DOI：10.1016/j.tetlet.2005.08.101

  日期：2005.10

  3-Substituted 3-isocyano propionates as new cleavable isocyanides in combinatorial tetrazole synthesis via Ugi-reaction are introduced. The obtained 5-substituted tetrazoles are transformed into carboxylic acid isosteric 5-substituted 1H-tetrazoles under basic cleavage conditions. (c) 2005 Elsevier Ltd. All rights reserved.
• Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water
  作者：Thomas Buyck、Qian Wang、Jieping Zhu

  DOI：10.1021/ja506031h

  日期：2014.8.13

  Reaction of alpha-substituted alpha-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.