Propanedioic acid, heptylidene-, dimethyl ester | 124956-89-4

• 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: Propanedioic acid, heptylidene-, dimethyl ester
• 英文别名: dimethyl 2-heptylidenepropanedioate
• CAS: 124956-89-4
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: SCYKHSKEHBXKBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-6-methyltetrahydropyran-2-ol 、 Propanedioic acid, heptylidene-, dimethyl ester 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以44%的产率得到2-[1-(6-methyltetrahydropyran-2-yloxy)heptyl]malonic acid dimethyl ester
  参考文献：
  名称：

  Highly Stereoselective Intermolecular Oxy-Michael Addition Reaction to α,β-Unsaturated Malonate Esters

  摘要：

  The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl delta lactol to alkylidiene-, arylidene-, and heteroarylidenemalonate derivatives leading to the direct formation of THP*-protected beta-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.

  DOI：

  10.1021/ol049820x
• 作为产物：
  描述：

  庚醛 、 二溴丙二酸二甲酯 在 二正丁基碲 作用下， 反应 5.0h， 以66%的产率得到Propanedioic acid, heptylidene-, dimethyl ester
  参考文献：
  名称：

  α,β-不饱和羰基化合物与二溴丙二酸酯的碲辅助环丙烷化和烷基化

  摘要：

  在室温下，二丁基碲化物有助于 α,β-不饱和酮、酯和腈与二溴丙二酸酯的环丙烷化反应。此外，它还可以用相同的试剂进行醛的烷基化，包括α，β-不饱和醛。

  DOI：

  10.1246/bcsj.62.2105

文献信息

• A Straightforward Method for the Synthesis of Alkylidene and Arylidene Malonates Through Proline-Catalyzed Knoevenagel Condensation
  作者：Giuliana Cardillo、Serena Fabbroni、Luca Gentilucci、Massimo Gianotti、Alessandra Tolomelli

  DOI：10.1081/scc-120018782

  日期：2003.1.5

  Abstract A straightforward method for the synthesis of alkylidene/arylidene malonates and arylidene cyanoacetates, utilizing proline as an alternative to traditional catalysts is presented. A large number of unsaturated esters was obtained from the Knoevenagel reaction under very mild conditions and utilizing cheap reagents.

  摘要 提出了一种使用脯氨酸替代传统催化剂来合成亚烷基/亚芳基丙二酸酯和亚芳基氰基乙酸酯的简单方法。在非常温和的条件下，使用廉价的试剂，从 Knoevenagel 反应中获得了大量的不饱和酯。
• METHOD FOR PREPARING 2-(CYCLOHEXENYLENE) MALONIC ACID DERIVATIVE AND USE THEREOF
  申请人：Oriental (Luzhou) Agrochemicals. Co., Ltd.

  公开号：EP3564208A1

  公开（公告）日：2019-11-06

  Disclosed are a method for preparing 2-(cyclohexenylidene) malonic acid derivatives and uses thereof. In this method, an olefin and a 2-substituted malonic acid derivative are used as starting materials to prepare the 2-(cyclohexenylidene) malonic acid derivative in the presence of a catalyst through cyclization reaction. This method has the following advantages: (1) the method can be very efficiently used for the synthesis of highly sterically-hindered 2-(2,6-disubstituted cyclohexenylidene) malonic acid derivatives; (2) the reaction yield is high, the reaction conditions are mild, and the wastes are less, favorable for industrial production. More importantly, the present invention extends the further use of 2-(cyclohexenylidene)malonic acid derivatives in organic synthesis, especially in the synthesis of 2-aryl malonic acid derivatives and their corresponding drugs such as Pinoxaden.

  本发明公开了一种制备 2-(环己烯亚基)丙二酸衍生物的方法及其用途。在该方法中，以烯烃和 2-取代丙二酸衍生物为起始原料，在催化剂存在下通过环化反应制备 2-（环己烯亚基）丙二酸衍生物。该方法具有以下优点：(1)该方法可以非常高效地用于合成高立体阻碍的 2-(2,6-二取代环己烯亚基)丙二酸衍生物；(2)反应收率高，反应条件温和，废弃物少，有利于工业化生产。更重要的是，本发明拓展了 2-(环己烯亚基)丙二酸衍生物在有机合成中的进一步用途，特别是在合成 2-芳基丙二酸衍生物及其相应药物（如 Pinoxaden）中的用途。
• Method for preparing 2-(cyclohexenylidene) malonic acid derivatives and uses thereof
  申请人：ORIENTAL(LUZHOU) AGROCHEMICALS. CO., LTD

  公开号：US10836777B2

  公开（公告）日：2020-11-17

  Disclosed are a method for preparing 2-(cyclohexenylidene) malonic acid derivatives and uses thereof. In this method, an olefin and a 2-substituted malonic acid derivative are used as starting materials to prepare the 2-(cyclohexenylidene) malonic acid derivative in the presence of a catalyst through cyclization reaction. This method has the following advantages: (1) the method can be very efficiently used for the synthesis of highly sterically-hindered 2-(2,6-disubstituted cyclohexenylidene) malonic acid derivatives; (2) the reaction yield is high, the reaction conditions are mild, and the wastes are less, favorable for industrial production. More importantly, the present invention extends the further use of 2-(cyclohexenylidene)malonic acid derivatives in organic synthesis, especially in the synthesis of 2-aryl malonic acid derivatives and their corresponding drugs such as Pinoxaden.

  本发明公开了一种制备 2-(环己烯亚基)丙二酸衍生物的方法及其用途。在该方法中，以烯烃和 2-取代丙二酸衍生物为起始原料，在催化剂存在下通过环化反应制备 2-（环己烯亚基）丙二酸衍生物。该方法具有以下优点：(1)该方法可以非常高效地用于合成高立体阻碍的 2-(2,6-二取代环己烯亚基)丙二酸衍生物；(2)反应收率高，反应条件温和，废弃物少，有利于工业化生产。更重要的是，本发明拓展了 2-(环己烯亚基)丙二酸衍生物在有机合成中的进一步用途，特别是在合成 2-芳基丙二酸衍生物及其相应药物（如 Pinoxaden）中的用途。
• METHOD FOR PREPARING 2-(CYCLOHEXENYLIDENE) MALONIC ACID DERIVATIVES AND USES THEREOF
  申请人：ORIENTAL(LUZHOU) AGROCHEMICALS. CO., LTD

  公开号：US20190292200A1

  公开（公告）日：2019-09-26

  Disclosed are a method for preparing 2-(cyclohexenylidene) malonic acid derivatives and uses thereof. In this method, an olefin and a 2-substituted malonic acid derivative are used as starting materials to prepare the 2-(cyclohexenylidene) malonic acid derivative in the presence of a catalyst through cyclization reaction. This method has the following advantages: (1) the method can be very efficiently used for the synthesis of highly sterically-hindered 2-(2,6-disubstituted cyclohexenylidene) malonic acid derivatives; (2) the reaction yield is high, the reaction conditions are mild, and the wastes are less, favorable for industrial production. More importantly, the present invention extends the further use of 2-(cyclohexenylidene)malonic acid derivatives in organic synthesis, especially in the synthesis of 2-aryl malonic acid derivatives and their corresponding drugs such as Pinoxaden.