dimethyl (2R,3S)-2-hydroxy-3-allylsuccinate | 167539-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: dimethyl (2R,3S)-2-hydroxy-3-allylsuccinate
• 英文别名: 3-allylmalic dimethyl ester；dimethyl (2R,3S)-2-hydroxy-3-prop-2-enylbutanedioate
• CAS: 167539-28-8
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: RETPCTOLJHDCTG-NKWVEPMBSA-N

物化性质

• 沸点：
  288.0±40.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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 (2R,3S)-2-hydroxy-3-allylsuccinate 在 4-二甲氨基吡啶 、 三甲基溴硅烷 、 臭氧 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3S)-2-Hydroxy-3-methoxycarbonyl-pentanedioic acid 1-methyl ester 5-(2,2,2-trichloro-ethyl) ester
  参考文献：
  名称：

  Syntheses of isocitric acid derivatives and biological evaluation

  摘要：

  Isocitric acid methyl esters and their derivatives have been synthesized and their biological activities, superoxide release inhibition and tumor necrosis factor-alpha (TNF alpha)'s release inhibition, have been studied. Linoleic and linolenic acid derivatives showed strong activity against TNF alpha's release inhibition comparable to sarcophytol A and cryptoporic acid E. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00316-6
• 作为产物：
  描述：

  D-苹果酸二甲酯 、 3-溴丙烯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 dimethyl (2R,3S)-2-hydroxy-3-allylsuccinate
  参考文献：
  名称：

  Antifungal Activity of Homoaconitate and Homoisocitrate Analogs

  摘要：

  我们设计并合成了真菌 L-赖氨酸生物合成途径中 L-a-氨基己二酸盐两个初始中间体的 13 种结构类似物，包括高乌头酸盐和高异柠檬酸盐的氟和环氧衍生物。其中一些化合物在毫摩尔范围内对白色念珠菌的高乌头酸酶和/或高异柠檬酸脱氢酶表现出适度的酶抑制特性。酶-抑制剂复合物的分子模型揭示了同异柠檬酸脱氢酶抑制作用的结构基础。另一方面，一些新型化合物的三甲酯形式显示出抗真菌作用。反式高乌头酸三甲酯的抗真菌活性最高，它能抑制一些人类致病酵母菌的生长，最小抑制浓度（MIC）值为 16-32 毫克/毫升。

  DOI：

  10.3390/molecules171214022

文献信息

• Improved asymmetric syntheses of (R)-(−)-homocitrate and (2R,3S)-(−)-homoisocitrate, intermediates in the α-aminoadipate pathway of fungi
  作者：Guoxiang Ma、David R.J Palmer

  DOI：10.1016/s0040-4039(00)01707-x

  日期：2000.11

  Improved asymmetric syntheses of the title compounds are reported. Both products are produced through diastereoselective alkylation of malic acid; (R)-homocitrate synthesis uses the self-regeneration of stereocenters approach. Both procedures represent an improvement in yield over existing methods without loss of stereoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Syntheses of isocitric acid derivatives and biological evaluation
  作者：Motoo Tori、Yoko Sono、Yasuyo Nakashiba、Noriko Hamada、Masakazu Sono、Yoshinori Asakawa、Masami Suganuma、Sachiko Okabe、Hirota Fujiki

  DOI：10.1016/s0040-4039(00)00316-6

  日期：2000.4

  Isocitric acid methyl esters and their derivatives have been synthesized and their biological activities, superoxide release inhibition and tumor necrosis factor-alpha (TNF alpha)'s release inhibition, have been studied. Linoleic and linolenic acid derivatives showed strong activity against TNF alpha's release inhibition comparable to sarcophytol A and cryptoporic acid E. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Antifungal Activity of Homoaconitate and Homoisocitrate Analogs
  作者：Maria Milewska、Marta Prokop、Iwona Gabriel、Marek Wojciechowski、Sławomir Milewski

  DOI：10.3390/molecules171214022

  日期：——

  Thirteen structural analogs of two initial intermediates of the L-a-aminoadipate pathway of L-lysine biosynthesis in fungi have been designed and synthesized, including fluoro- and epoxy-derivatives of homoaconitate and homoisocitrate. Some of the obtained compounds exhibited at milimolar range moderate enzyme inhibitory properties against homoaconitase and/or homoisocitrate dehydrogenase of Candida albicans. The structural basis for homoisocitrate dehydrogenase inhibition was revealed by molecular modeling of the enzyme-inhibitor complex. On the other hand, the trimethyl ester forms of some of the novel compounds exhibited antifungal effects. The highest antifungal activity was found for trimethyl trans-homoaconitate, which inhibited growth of some human pathogenic yeasts with minimal inhibitory concentration (MIC) values of 16–32 mg/mL.

  我们设计并合成了真菌 L-赖氨酸生物合成途径中 L-a-氨基己二酸盐两个初始中间体的 13 种结构类似物，包括高乌头酸盐和高异柠檬酸盐的氟和环氧衍生物。其中一些化合物在毫摩尔范围内对白色念珠菌的高乌头酸酶和/或高异柠檬酸脱氢酶表现出适度的酶抑制特性。酶-抑制剂复合物的分子模型揭示了同异柠檬酸脱氢酶抑制作用的结构基础。另一方面，一些新型化合物的三甲酯形式显示出抗真菌作用。反式高乌头酸三甲酯的抗真菌活性最高，它能抑制一些人类致病酵母菌的生长，最小抑制浓度（MIC）值为 16-32 毫克/毫升。