isobutyl α-diazo-α-(diethoxyphosphoryl)acetate | 628729-57-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: isobutyl α-diazo-α-(diethoxyphosphoryl)acetate
• 英文别名: 2-methylpropyl 2-diazo-2-(diethoxyphosphoryl)acetate；2-methylpropyl (2Z)-2-diazo-2-diethoxyphosphorylacetate
• CAS: 628729-57-7
• 化学式: C₁₀H₁₉N₂O₅P
• 分子量: 278.245
• InChiKey: WIEKCPUBTOBSGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isobutyl α-diazo-α-(diethoxyphosphoryl)acetate 在 辛酸铑 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 4,4-dimethyl-3-methylenedihydrofuran-2(3H)-one
  参考文献：
  名称：

  α-Alkylidene-γ-butyrolactone synthesis via one-pot C–H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B

  摘要：

  A system for the synthesis of alpha-alkylidene-gamma-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of alpha-diazoa-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (+/-)-cedarmycins A and B is also described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.054
• 作为产物：
  描述：

  isobutyl α-(diethoxyphosphoryl)acetate 在 对甲苯磺酰叠氮 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以77%的产率得到isobutyl α-diazo-α-(diethoxyphosphoryl)acetate
  参考文献：
  名称：

  α-重氮-α-(二烷氧基磷酰基)乙酰胺和-乙酸盐的区域选择性和立体选择性二铑(II)-催化的分子内C-H插入反应

  摘要：

  α-重氮-α-（二烷氧基磷酰基）乙酸酯和 -乙酰胺分别通过二铑（II）催化的分子内碳氢插入反应以中等至高产率提供了 α-（二烷氧基磷酰基）内酯和内酰胺。在α-重氮-α-（二烷氧基磷酰基）乙酰胺的情况下，观察到显着偏好形成γ-内酰胺，立体控制有利于反式非对映异构体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300330

文献信息

• [EN] PURINE DERIVATIVES AS CD73 INHIBITORS FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE PURINE EN TANT QU'INHIBITEURS DE CD73 POUR LE TRAITEMENT DU CANCER
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2015164573A1

  公开（公告）日：2015-10-29

  Provided are novel compounds, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are inhibitors of CD73 and are useful in the treatment of cancer.

  提供的是新颖化合物、其药学上可接受的盐以及其药物组合物，这些化合物是CD73的抑制剂，并可用于癌症治疗。
• Regio- and Stereoselective Dirhodium(II)-Catalysed Intramolecular C−H Insertion Reactions ofα-Diazo-α-(dialkoxyphosphoryl)acetamides and -acetates
  作者：Pedro M. P. Gois、Carlos A. M. Afonso

  DOI：10.1002/ejoc.200300330

  日期：2003.10

  α-Diazo-α-(dialkoxyphosphoryl)acetates and -acetamides afforded α-(dialkoxyphosphoryl)lactones and lactams, respectively, in moderate to high yields through dirhodium(II)-catalysed intramolecular carbon−hydrogen insertion reactions. In the case of α-diazo-α-(dialkoxyphosphoryl)acetamides a remarkable preference for the formation of γ-lactam was observed, with stereocontrol in favour of the trans diastereomer

  α-重氮-α-（二烷氧基磷酰基）乙酸酯和 -乙酰胺分别通过二铑（II）催化的分子内碳氢插入反应以中等至高产率提供了 α-（二烷氧基磷酰基）内酯和内酰胺。在α-重氮-α-（二烷氧基磷酰基）乙酰胺的情况下，观察到显着偏好形成γ-内酰胺，立体控制有利于反式非对映异构体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Purine derivatives as CD73 inhibitors for the treatment of cancer
  申请人：Vitae Pharmaceuticals, Inc.

  公开号：US10654884B2

  公开（公告）日：2020-05-19

  Provided are novel purine nucleoside/nucleotide analogues compounds, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are inhibitors of CD73 and are useful in the treatment of cancer.

  本文提供了新型嘌呤核苷/核苷酸类似物化合物、其药学上可接受的盐及其药物组合物，它们是 CD73 的抑制剂，可用于治疗癌症。
• PURINE DERIVATIVES AS CD73 INHIBITORS FOR THE TREATMENT OF CANCER
  申请人：Vitae Pharmaceuticals, Inc.

  公开号：EP3134411A1

  公开（公告）日：2017-03-01
• α-Alkylidene-γ-butyrolactone synthesis via one-pot C–H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
  作者：Matthew G. Lloyd、Mariantonietta D'Acunto、Richard J.K. Taylor、William P. Unsworth

  DOI：10.1016/j.tet.2014.09.054

  日期：2015.9

  A system for the synthesis of alpha-alkylidene-gamma-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of alpha-diazoa-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (+/-)-cedarmycins A and B is also described. (C) 2014 Elsevier Ltd. All rights reserved.