dimethyl 2-(4-hydroxybutyl)malonate | 180259-49-8

• 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 2-(4-hydroxybutyl)malonate
• 英文别名: 2-(4-Hydroxy-butyl)-malonic acid dimethyl ester；Dimethyl 2-(4-hydroxybutyl)propanedioate；dimethyl 2-(4-hydroxybutyl)propanedioate
• CAS: 180259-49-8
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: XWXXEVADEDUIAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(4-hydroxybutyl)malonate 在 caesium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (E)-(S)-13-(Toluene-4-sulfonyl)-2-oxa-13-aza-bicyclo[14.2.2]icosa-1(19),9,16(20),17-tetraene-7,7,14-tricarboxylic acid trimethyl ester
  参考文献：
  名称：

  Design and synthesis of macro-heterocycles structurally related to tirofiban

  摘要：

  Sequences of nine and four steps were designed to yield two tirobifan related macrocycles by SN2 macrocyclization. The cyclic compounds contain the amino acid tyrosine, one insaturation and are either 18- or 20-membered rings. All the reaction conditions are very mild and the overall yields indicate that the results depend a lot on the structure of the targets and on the length of the reaction sequence. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00709-7
• 作为产物：
  描述：

  2-[4'-(Tetrahydro-2-pyranyloxy)butyl]-malonic acid dimethyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以96%的产率得到dimethyl 2-(4-hydroxybutyl)malonate
  参考文献：
  名称：

  Design and synthesis of macro-heterocycles structurally related to tirofiban

  摘要：

  Sequences of nine and four steps were designed to yield two tirobifan related macrocycles by SN2 macrocyclization. The cyclic compounds contain the amino acid tyrosine, one insaturation and are either 18- or 20-membered rings. All the reaction conditions are very mild and the overall yields indicate that the results depend a lot on the structure of the targets and on the length of the reaction sequence. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00709-7

文献信息

• Selective hydroboration of equilibrating allylic azides
  作者：Ruzhang Liu、Yuanyuan Zhang、Jun Xu

  DOI：10.1039/d1cc02520a

  日期：——

  The iridium(I)-catalyzed hydroboration of equilibrating allylic azides is reported to provide only the anti-Markovnikov product of alk-1-ene isomers in good yields and with good functional group tolerance.

  据报道，平衡的烯丙基叠氮化物的铱( I ) 催化硼氢化仅以良好的收率和良好的官能团耐受性提供了烷-1-烯异构体的反马尔科夫尼科夫产物。
• A mild method for generation of p-methoxybenzyl cation through NIS-mediated activation of p-methoxybenzyl 4-pentenyl ether
  作者：Midori Okada、Osamu Kitagawa、Masao Fujita、Takeo Taguchi

  DOI：10.1016/0040-4020(96)00375-4

  日期：1996.6

  A mild and facile method for generation of p-methoxybenzyl cation through NIS-mediated activation of p-methoxybenzyl 4-pentenyl ether was achieved. Under the present activation conditions, various alcohols were converted to the corresponding p-methoxybenzyl ethers. A scope and limitation of the present p-methoxybenzylation reaction was also investigated.

  实现了通过NIS介导的对-甲氧基苄基4-戊烯基醚的活化来产生对-甲氧基苄基阳离子的温和而简便的方法。在当前的活化条件下，各种醇被转化为相应的对甲氧基苄基醚。还研究了本对甲氧基苄基化反应的范围和局限性。
• Design of an organic sequence suitable for the solid phase combinatorial synthesis of libraries of macro-heterocycles
  作者：Mahesh Ramaseshan、John W Ellingboe、Yves L Dory、Pierre Deslongchamps

  DOI：10.1016/s0040-4039(00)00710-3

  日期：2000.6

  The solid as well as solution phase synthesis of two 14-membered macro-heterocycles is reported. The macrocycles are built out of four or three major building blocks and contain serine, a trans alkene and the malonate unit inside the framework. The macrocyclization was an SN2 reaction between a nucleophilic malonate anion and an allylic chloride leaving group. The first macrocycle, an ether, was obtained

  报道了两个14元大杂环的固相和溶液相合成。大环由四个或三个主要组成部分构成，并在框架内包含丝氨酸，反式烯烃和丙二酸酯单元。大环化是亲核丙二酸根阴离子和烯丙基氯离去基团之间的SN2反应。获得第一个大环醚，即醚，在固体载体上进行的11步总收率为8％，与溶液中11％的收率相似。在六个步骤中，第二目标大内酯的固相总产率为45％，高于溶液中的总产率（35％）。DHP接头对各种试剂和反应条件的稳定性是值得注意的。
• Palladium-Catalyzed Remote Hydro-Oxygenation of Internal Alkenes: An Efficient Access to Primary Alcohols
  作者：Xiang Li、Xintuo Yang、Pinhong Chen、Guosheng Liu

  DOI：10.1021/jacs.2c11428

  日期：2022.12.21
• Design and synthesis of macro-heterocycles structurally related to tirofiban
  作者：Mahesh Ramaseshan、Martin Robitaille、John W Ellingboe、Yves L Dory、Pierre Deslongchamps

  DOI：10.1016/s0040-4039(00)00709-7

  日期：2000.6

  Sequences of nine and four steps were designed to yield two tirobifan related macrocycles by SN2 macrocyclization. The cyclic compounds contain the amino acid tyrosine, one insaturation and are either 18- or 20-membered rings. All the reaction conditions are very mild and the overall yields indicate that the results depend a lot on the structure of the targets and on the length of the reaction sequence. (C) 2000 Published by Elsevier Science Ltd.