dimethyl ester of 1,3-dioxolan-2-yl succinic acid | 88820-09-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl ester of 1,3-dioxolan-2-yl succinic acid
• 英文别名: 2-(1,3-dioxolan-2-yl)butanedioic acid 1,4-dimethyl ester；dimethyl 2-(1,3-dioxolan-2-yl)butanedioate
• CAS: 88820-09-1
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: HYMPSERZSFKAGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-二氧戊环 、 1,4-dimethyl but-2-enedioate 在 (Bu₄N)₂S₂O₈ 作用下， 反应 1.5h， 以98%的产率得到dimethyl ester of 1,3-dioxolan-2-yl succinic acid
  参考文献：
  名称：

  Practical β-masked formylation and acetylation of electron-deficient olefins utilizing tetra(n-butyl)ammonium peroxydisulfate

  摘要：

  Various electron-deficient olefins reacted readily with 1,3-dioxolane or 2-methyl-1,3-dioxlane in the presence of TBAP to afford the corresponding 1,3-dioxolanylated or 2-methyl-1,3-dioxolanylated products in a complete regioselective manner in good to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.116

文献信息

• Hydrogen Atom Transfer Reactions via Photoredox Catalyzed Chlorine Atom Generation
  作者：Samantha Rohe、Avery O. Morris、Terry McCallum、Louis Barriault

  DOI：10.1002/anie.201810187

  日期：2018.11.26

  waste‐limiting, and atom‐economical. The catalytic generation of chlorine atoms from chloride ions is one of the most challenging redox processes, where the requirement of harsh and oxidizing reaction conditions renders it seldom utilized in synthetic applications. We report the mild, controlled, and catalytic generation of chlorine atoms as a new opportunity for access to a wide variety of hydrogen atom transfer

  在实现氧化还原中性，废物限制和原子经济的有机转化中，化学惰性CH键的选择性官能化仍有待充分实现。由氯离子催化生成氯原子是最具挑战性的氧化还原过程之一，在苛刻和氧化反应条件下的需求使其很少用于合成应用。我们报告说，由于HCl的高稳定性，氯原子的温和，受控和催化生成是获得各种氢原子转移（HAT）反应的新机会。报道了在蓝光LED照射下，基于Ir的聚吡啶基络合物[Ir（dF（CF 3）ppy）2（dtbbpy）] Cl的光氧化还原介导的氯原子生成的发现。
• Photochemical addition of cyclic ethers/acetals to olefins using BuOO Bu: Synthesis of masked ketones/aldehydes and diols
  作者：Mamiko Hayakawa、Rina Shimizu、Hajime Omori、Hisashi Shirota、Kou Uchida、Hiroshi Mashimo、Han Xu、Ryuusei Yamada、Seiya Niino、Yoshiki Wakame、Chuanxiang Liu、Tadashi Aoyama、Akihiko Ouchi

  DOI：10.1016/j.tet.2020.131557

  日期：2020.10

  A fast photochemical C–C bond formation between cyclic ethers/acetals and olefins using di-tert-butyl peroxide (DTBP) was developed. This method provides easy access to 2-substituted cyclic ethers, and 2- or 4-substituted cyclic acetals. Acyl/formyl groups or diols can be obtained by the hydrolysis of the 2- or 4-substituted cyclic acetals, respectively. The reactions proceeded at room temperature

  开发了使用二叔丁基过氧化物（DTBP）在环状醚/缩醛与烯烃之间快速形成光化学C-C键的方法。此方法可轻松获得2-取代的环醚和2-或4-取代的环缩醛。酰基/甲酰基或二醇可分别通过2-或4-取代的环状缩醛的水解获得。反应在室温下进行，得到预期的产物，收率良好至极好。在室温下0.5小时内完成高效反应，收率> 95％。
• Formylation of Fluoroalkyl Imines through Visible-Light-Enabled H-Atom Transfer Catalysis: Access to Fluorinated α-Amino Aldehydes
  作者：Sen Yang、Shuangyu Zhu、Dengfu Lu、Yuefa Gong

  DOI：10.1021/acs.orglett.9b00128

  日期：2019.4.5

  visible-light-enabled catalytic formylation of fluoroalkyl imines is developed. With readily accessible starting materials and organocatalysts, this method provides a general approach to masked fluoroalkyl amino aldehydes. A synergistic catalytic effect between the photosensitizer and the H atom transfer agent was proven pivotal to this transformation. After removing the mask, free aldehydes can be obtained and

  开发了可见光使氟代烷基亚胺催化甲酰化。利用容易获得的起始原料和有机催化剂，该方法提供了掩蔽的氟代烷基氨基醛的一般方法。光敏剂和氢原子转移剂之间的协同催化作用被证明对这种转化至关重要。除去掩膜后，可以获得游离醛并将其进一步转化为各种β-氟烷基β-氨基醇，它们是生物活性和药物化合物合成中的有吸引力的构建基块。
• Carbon Nitride Photoredox Catalysis Enables the Generation of the Dioxolanyl Radical for Conjugate Addition Reactions
  作者：Viktoria C. Gerken、Erick M. Carreira

  DOI：10.1021/acscatal.2c03229

  日期：2022.9.2

  Graphitic carbon nitride (g-C3N4) is used as photocatalyst in the Giese reaction of dioxolane and a wide variety of electron-deficient olefins. The catalyst is shown to be reusable over five cycles with no changes in catalyst composition, morphology, and characteristics observed by scanning electron microscopy, elemental analysis, infrared spectroscopy, and powder X-ray diffraction.

  石墨氮化碳 (gC 3 N 4 ) 在二氧戊环和多种缺电子烯烃的 Giese 反应中用作光催化剂。经扫描电子显微镜、元素分析、红外光谱和粉末 X 射线衍射观察，该催化剂可重复使用五个循环，催化剂组成、形态和特性没有变化。
• Safiev, O. G.; Kruglov, D. E.; Popov, Yu. N., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 5, p. 997 - 1000
  作者：Safiev, O. G.、Kruglov, D. E.、Popov, Yu. N.、Zlot-skii, S. S.、Rakhmankulov, D. L.

  DOI：——

  日期：——