methyl 2-hydroxy-4-pentenoate | 96488-05-0

• 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: methyl 2-hydroxy-4-pentenoate
• 英文别名: (2R)-2-hydroxypent-4-enoic acid methyl ester；methyl (2R)-2-hydroxypent-4-enoate；(R)-2-Hydroxy-pent-4-enoic acid methyl ester；(R)-Methyl 2-hydroxypent-4-enoate
• CAS: 96488-05-0
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: JZBUJSFCZCCWBE-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-4-pentenoate 生成 (2R)-2-Hydroxypentanoic acid methyl ester
  参考文献：
  名称：

  MIKAMI, KOICHI;FUJIMOTO, KATSUHIKO;KASUGA, TAKASHI;NAKAI, TAKESHI, TETRAHEDRON LETT., 1984, 25, N 52, 6011-6014

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醛酸甲酯 、 烯丙基三甲基硅烷 在 盐酸 、 (R)-binaphthol-titanium dichloride ((R)-BINOL-TiCl₂) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以44%的产率得到methyl 2-hydroxy-4-pentenoate
  参考文献：
  名称：

  Ene approach to asymmetric catalysis of the “Sakurai-Hosomi reaction”, Lewis acid-promoted carbonyl-addition reaction with allylic silanes

  摘要：

  The chiral Lewis acid prepared from (R)-binaphthol and diisopropoxytitanium dichloride catalyzes the reaction of glyoxylate esters with methallylsilanes to afford mainly ene-type products rather than the products expected from the ''usual'' Sakurai-Hosomi reaction. The ene-type products lead eventually after protodesilylation to the ''usual'' products with high enantiomeric excesses.

  DOI：

  10.1016/s0040-4039(00)76849-3

文献信息

• AMPHOTERICIN B DERIVATIVES WITH IMPROVED THERAPEUTIC INDEX
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20160215012A1

  公开（公告）日：2016-07-28

  Provided are certain derivatives of amphotericin B (AmB) characterized by reduced toxicity and retained anti-fungal activity. Certain of the derivatives are C16 urea derivatives of AmB. Certain of the derivatives are C3, C5, C8, C9, C11, C13, or C15 deoxy derivatives of AmB. Certain of the derivatives include C3′ or C4′ modifications of the mycosamine appendage of AmB. Also provided are methods of making AmB derivatives of the invention, pharmaceutical compositions comprising AmB derivatives of the invention, and methods of use of AmB derivatives of the invention.

  提供了一些特定的两性霉素B（AmB）衍生物，其具有降低毒性和保留抗真菌活性的特点。其中一些衍生物是AmB的C16脲衍生物。其中一些衍生物是AmB的C3、C5、C8、C9、C11、C13或C15去氧衍生物。其中一些衍生物包括对AmB的甲氨葡萄糖胺附属物的C3′或C4′修饰。还提供了制备该发明的AmB衍生物的方法，包括该发明的AmB衍生物的药物组合物，以及该发明的AmB衍生物的使用方法。
• A unified strategy for the total syntheses of eribulin and a macrolactam analogue of halichondrin B
  作者：K. C. Nicolaou、Saiyong Pan、Yogesh Shelke、Stephan Rigol、Ruiyang Bao、Dipendu Das、Qiuji Ye

  DOI：10.1073/pnas.2208938119

  日期：2022.8.9

  all-carbon macrocyclic framework of eribulin. These syntheses, together with our previous work on the total syntheses of halichondrin B and norhalichondrin B, demonstrate and validate the powerful reverse approach in the construction of cyclic ether structural motifs. On the other hand, the unified synthetic strategy for the synthesis of the related macrolactam analog provides inspiration and opportunities

  描述了用于全合成艾日布林和软软骨素 B 的大环内酰胺类似物的统一合成路线。当前合成方法成功的关键包括使用我们的逆向方法构建环状醚结构基序以及烷基碘和醛官能团之间的改进分子内环化反应以建立艾日布林的全碳大环框架。这些合成，连同我们之前关于软软骨素 B 和去甲软藻素 B 的全合成的工作，证明并验证了构建环醚结构基序的强大逆向方法。另一方面，
• [EN] NEW CONTRAST AGENT FOR USE IN MAGNETIC RESONANCE IMAGING<br/>[FR] NOUVEL AGENT DE CONTRASTE DESTINÉ À ÊTRE UTILISÉ DANS L'IMAGERIE PAR RÉSONANCE MAGNÉTIQUE
  申请人：BAYER AG

  公开号：WO2022194777A1

  公开（公告）日：2022-09-22

  The present invention relates to a new class of compounds of general formula (I), the Gd3+chelate complexes thereof, to methods of preparing said compounds, and to the use of said compounds as MRI contrast agents. Formula (I)

  本发明涉及一类新的通式（I）化合物、其钆3+螯合物、制备上述化合物的方法以及上述化合物作为 MRI 造影剂的用途。通式 (I)
• Enantioselective [2,3]-Wittig Rearrangement of Carboxylic Acid Derived Enolates by Tetradentate Chiral Lithium Amide
  作者：Ryuichi Shirai、Kenji Yatsuzuka、Midori Kawasaki

  DOI：10.1055/a-2039-6352

  日期：——

  A chiral lithium amide mediated enantioselective [2,3]-Wittig rearrangement of carboxylic acid enolate has been developed. The reaction proceeds through the formation of a chiral mixed aggregate that shields one enantioface of enolate anion to give a highly functionalized chiral α-hydroxycarboxylic acid.

  摘要 开发了一种手性锂酰胺介导的羧酸对映体选择性 [2,3]-Wittig 重排反应。该反应通过形成手性混合聚集体来屏蔽烯酸根阴离子的一个对映面，从而得到高度官能化的手性α-羟基羧酸。
• A facile synthesis of chiral ω-allyl- and ω-n-propyllactones via asymmetric allylboration of formyl esters with B-allyldiisopinocampheylborane
  作者：P.Veeraraghavan Ramachandran、Marek P. Krzeminski、M.Venkat Ram Reddy†、Herbert C. Brown

  DOI：10.1016/s0957-4166(98)00477-7

  日期：1999.1

  Asymmetric allylboration of aldehydes containing an adjacent ester group with B-allyldiisopinocampheylborane, followed by hydrolysis and cyclization, provides the corresponding allyl substituted lactones in high yields and greater than or equal to 92% enantiomeric excess. Hydrogenation of these lactones provides the corresponding propyl substituted lactones without any loss of optical purity. (C) 1999 Elsevier Science Ltd. All rights reserved.