cis-Cyclohexane-1,2-dicarboxylic acid dibutyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-Cyclohexane-1,2-dicarboxylic acid dibutyl ester
• 英文别名: dibutyl (1S,2R)-cyclohexane-1,2-dicarboxylate
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: ANSWCYTXKAIJOK-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲酸丁酯 、 (1R,2S)-cyclohexane-1,2-dicarboxylic acid 在 Dowex 50Wx₂ 作用下， 以 正辛烷 为溶剂， 反应 17.0h， 以89%的产率得到cis-Cyclohexane-1,2-dicarboxylic acid monobutyl ester
  参考文献：
  名称：

  Selective monoesterification of dicarboxylic acids catalysed by ion-exchange resins

  摘要：

  具有4至14个碳原子的对称二羧酸在强酸性离子交换树脂催化下的转酯化反应中，可以在酯-烃混合物中高选择性地获得相应的单酯，产率很高。研究发现，二羧酸的酯化速率远高于形成的单羧酸的速率。这一结果可以解释单酯形成的高选择性，也可以通过树脂表面存在的水层来解释。这种选择性酯化方法相当简单且实用。

  DOI：

  10.1039/a902325i

文献信息

• Production of Plant Phthalate and its Hydrogenated Derivative from Bio-Based Platform Chemicals
  作者：Rui Lu、Fang Lu、Xiaoqin Si、Huifang Jiang、Qianqian Huang、Weiqiang Yu、Xiangtao Kong、Jie Xu

  DOI：10.1002/cssc.201800646

  日期：2018.5.25

  into aromatic dicarboxylic acids and their derivatives, which are widely used for the manufacture of polymers, is of significant importance for the sustainable development of the plastics industry. However, limited successful chemical processes have been reported. This study concerns a sustainable route for the production of phthalate and its hydrogenated derivative from bio‐based malic acid and erythritol

  将基于生物的平台化学品直接转化为芳族二羧酸及其衍生物（已广泛用于制造聚合物），对于塑料工业的可持续发展具有重要意义。然而，已经报道了有限的成功化学过程。这项研究涉及从生物基苹果酸和赤藓糖醇生产邻苯二甲酸酯及其氢化衍生物的可持续途径。关键的Diels–Alder反应用于构建取代的环己烯结构。苹果酸的脱水反应可得到富马酸，收率为96.6％，可作为亲二烯体，通过赤藓糖醇脱氧脱水原位生成的1,3-丁二烯可作为二烯。从赤藓糖醇和富马酸二丁酯开始，产率为74.3％获得反式-4-环己烯1,2-二羧酸酯。钯催化环加合物的脱氢反应可得到77.8％的邻苯二甲酸二丁酯收率。在温和的条件下，通过环加合物的氢化反应，可以以接近100％的产率生成反式正环己烷-1，2-二羧酸二丁酯。此外，根据实验和计算结果，富马酸和富马酸盐具有反式构型，对于Diels-Alder反应，它比顺式构型的马来酸和马来酸盐具有更好的双亲性。这
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