5-氧代吡咯烷-1,2-二羧酸 1-苄基酯 | 80953-62-4

• 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: 5-氧代吡咯烷-1,2-二羧酸 1-苄基酯
• 中文别名: N-CBZ-DL-焦谷氨酸；N-Cbz-DL-焦谷氨酸；5-氧代吡咯烷-1,2-二羧酸1-苄基酯
• 英文名称: N-benzyloxycarbonyl-pyroglutamic acid
• 英文别名: N-(benzyloxycarbonyl)-2-pyrrolidone-2-carboxylic acid；Z-Pyr-OH；1-benzyl hydrogen 5-oxopyrrolidine-1,2-dicarboxylate；1-[(Benzyloxy)carbonyl]-5-oxoproline；5-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 80953-62-4
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: VHSFUGXCSGOKJX-UHFFFAOYSA-N

物化性质

• 沸点：
  525.4±50.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氧代吡咯烷-1,2-二羧酸 1-苄基酯 在 sodium methylate 、 四氯化锡 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 [4-(5-Fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-butyryl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthetic electroorganic chemistry. 14. Synthesis of 5-fluorouracil derivatives having N-acylazacycloalkanes and lactams

  摘要：

  DOI：

  10.1021/jo00348a020

文献信息

• THERAPEUTIC AGENT FOR DIABETES
  申请人：Japan Tobacco Inc.

  公开号：EP0885869A1

  公开（公告）日：1998-12-23

  A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4 and R5 are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6 is a hydrogen atom or an amino-protecting group; R1 is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2 is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3 is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.

  用于治疗糖尿病的疗法剂，包括公式[I]的化合物 其中 X是公式的组 其中R4和R5相同或不同，每个都是氢原子，可选地取代的具有1至5个碳原子的烷基等等，R6是氢原子或氨基保护基团；R1是具有1至5个碳原子的可选取代烷基，具有2至6个碳原子的可选取代烯基等等，R2是氢原子，具有1至5个碳原子的可选取代烷基等等，R2'是氢原子，R3是具有1至5个碳原子的可选取代烷基等等，其前药，药用可接受盐，水合物和溶剂化物。 本发明的化合物在血糖升高状态下表现出优越的降血糖作用，但在正常范围或低血糖状态下不影响血糖，这意味着它没有低血糖等严重副作用。因此，本发明的化合物作为治疗糖尿病的药物很有用，也用作预防糖尿病慢性并发症。
• Photochemical Strain‐Release‐Driven Cyclobutylation of C(sp ³ )‐Centered Radicals
  作者：Guillaume Ernouf、Egor Chirkin、Lydia Rhyman、Ponnadurai Ramasami、Jean‐Christophe Cintrat

  DOI：10.1002/anie.201908951

  日期：2020.2.10

  bicyclo[1.1.0]butanes. The mild photoredox conditions, which make use of a readily available and bench stable phenyl sulfonyl bicyclo[1.1.0]butane, proved to be amenable to a diverse range of α-amino and α-oxy carboxylic acids, providing a concise route to 1,3-disubstituted cyclobutanes. Furthermore, kinetic studies and DFT calculations unveiled mechanistic details on bicyclo[1.1.0]butane reactivity relative

  描述了一种新的光氧化还原催化的脱羧自由基加成方法，以官能化的环丁烷。该反应涉及到以高应变的双环[1.1.0]丁烷空前的以C（sp3）为中心的形式正式的Giese型加成反应。轻度的光氧化还原条件，利用易于获得且稳定的苯磺酰基双环[1.1.0]丁烷，证明适用于各种范围的α-氨基和α-氧基羧酸，提供了简化的制备1 ，3-二取代的环丁烷。此外，动力学研究和DFT计算揭示了相对于相应的烯烃体系双环[1.1.0]丁烷反应性的机理细节。
• ADENINE DERIVATIVES
  申请人：Buchstaller Hans-Peter

  公开号：US20100160352A1

  公开（公告）日：2010-06-24

  Novel adenine derivatives of the formula (I), in which R 1 , R 2 , R 3 , X and Y have the meanings indicated in Claim 1 , are HSP90 inhibitors and can be used for the preparation of a medicament for the treatment of diseases in which the inhibition, regulation and/or modulation of HSP90 plays a role.

  新型腺嘌呤衍生物的化学式（I），其中R1、R2、R3、X和Y具有权利要求1中指示的含义，是HSP90抑制剂，可用于制备用于治疗需要HSP90抑制、调节和/或调控的疾病的药物。
• OPTICALLY ACTIVE DIAZABICYCLOOCTANE DERIVATIVES AND PROCESS FOR PREPARING THE SAME
  申请人：ABE Takao

  公开号：US20120165533A1

  公开（公告）日：2012-06-28

  Provided are an optically active diazabicyclooctane derivative defined by formula (F) below, which is useful as a pharmaceutical intermediate for β-lactamase inhibitor, and a process for preparing the same. In formula (F) above, R 1 represents CO 2 R, CO 2 M, or CONH 2 , wherein R represents a methyl group, a tert-butyl group, an allyl group, a benzyl group, or a 2,5-dioxopyrrolidin-1-yl group, and M represents a hydrogen atom, an inorganic cation, or an organic cation; and R 2 represents a benzyl group or an allyl group.

  提供了一个光学活性的二氮杂双环辛烷衍生物，其由下面的式（F）定义，可用作β-内酰胺酶抑制剂的药用中间体，以及制备该衍生物的方法。在上述的式（F）中，R1代表CO2R、CO2M或CONH2，其中R代表甲基基团、叔丁基基团、烯丙基团、苄基团或2,5-二氧代吡咯烷-1-基团，M代表氢原子、无机阳离子或有机阳离子；R2代表苄基团或烯丙基团。
• Synthesis of a New Dual Metalloprotease Inhibitor. I. Diastereoselective Alkylation of Protected 6-Oxopipecolic Acid Esters.
  作者：Kozo AKASAKA、Hiroshi AKAMATSU、Yuichi KIMOTO、Yuki KOMATSU、Toshikazu SHIMIZU、Naoyuki SHIMOMURA、Katsuya TAGAMI、Shigeto NEGI

  DOI：10.1248/cpb.47.1525

  日期：——

  Diastereoselective methylation of the enolate generated from various protected 6-oxopipecolic acid esters (3aa-3cd) was studied. The protecting groups on the carboxylic acid and amino groups significantly influenced the trans/cis selectivity in the methylation reaction. The optimal substrate (3ca), bearing benzhydryl ester and carbobenzyloxy moieties gave a trans/cis isomer ratio of ca. 4 : 1. Investigation of the reaction conditions revealed that the reaction solvent, alkylating reagent, and base employed to generate the enolate, were decisive factors for diastereoselectivity. Further optimization of reaction conditions, including the amounts of the reagents and their addition sequence enabled maximization of reaction conversion and minimization of by-products to produce the trans rich 5-methyl-6-oxopipecolic acid ester (4ca) on a large scale.

  研究了各种受保护的 6-氧代联哌啶酸酯（3aa-3cd）生成的对映体的非对映选择性甲基化反应。羧酸和氨基上的保护基团对甲基化反应的反式/顺式选择性有显著影响。带有苄基酯和苄氧基的最佳底物（3ca）的反式/顺式异构体比率约为 4 ：1.对反应条件的研究表明，生成对映体所使用的反应溶剂、烷基化试剂和碱是影响非对映选择性的决定性因素。进一步优化反应条件，包括试剂用量和加成顺序，可以最大限度地提高反应转化率，减少副产物，从而大规模生产出富含反式的 5-甲基-6-氧代联哌啶酸酯 (4ca)。

表征谱图