dimethyl (-)-menthoxycarbonyl-S-malate | 127275-06-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: dimethyl (-)-menthoxycarbonyl-S-malate
• 英文别名: Dimethyl (menthoxycarbonyl)-S-malate；dimethyl (2S)-2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxycarbonyloxybutanedioate
• CAS: 127275-06-3
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: KOHIJQLEVHSPRS-RQJABVFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  menthoxycarbonate derivative of 12(S)-HETE methyl ester 在 双氧水 、 臭氧 作用下， 反应 16.17h， 生成 dimethyl (-)-menthoxycarbonyl-S-malate
  参考文献：
  名称：

  合成12-氢过氧二十碳四烯酸（12-HPETE）。关于12（S）-HETE转化为12-HPETE的立体化学

  摘要：

  合成了12（S）-羟基二十碳四烯酸甲酯1。将图1的产物转化为亚磷酸酯17，将其用过氧化氢处理后得到部分保留构型的相应氢过氧化物18（12-HPETE甲酯）。

  DOI：

  10.1016/s0040-4039(00)99133-0

文献信息

• Solandelactones A-I, lactonized cyclopropyl oxylipins isolated from the hydroid Solanderia secunda
  作者：Youngwan Seo、Ki Woong Cho、Jung-Rae Rho、Jongheon Shin、Byoung-Mog Kwon、Song-Hae Bok、Jun-Im Song

  DOI：10.1016/0040-4020(96)00606-0

  日期：1996.8

  novel docosanoids have been isolated from the hydroid Solanderia secunda. The structures of these compounds have been elucidated by combined spectral and chemical studies. Configuration of the cyclopropyl ring has been assigned as the opposite of related oxylipins by NOESY experiments. Absolute stereochemistry has been determined on the basis of chemical transformations and CD measurements of synthetic

  Solandelactones AI（1–9），环丙基和内酯类化合物含有新的类二十烷酸，已从亲水的Solanderia secunda中分离出来。这些化合物的结构已通过结合光谱和化学研究得以阐明。通过NOESY实验，已将环丙基环的构型指定为与相关脂蛋白相反的构型。绝对立体化学已经基于化学转化和合成衍生物的CD测量确定。另外，已经讨论了苏兰内酯的生物遗传起源。Solandelactones C，D和G表现出对法呢基蛋白转移酶的中等抑制活性。
• Structure and stereochemistry of constanolactones A-G, lactonized cyclopropyl oxylipins from the red marine alga Constantinea simplex
  作者：Dale G. Nagle、William H. Gerwick

  DOI：10.1021/jo00103a012

  日期：1994.12

  Extracts of the Oregon marine alga Constantinea simplex were found to contain a mixture of omega 6 and omega 3 unsaturated constanolactones, lactonized cyclopropyl-containing metabolites that logically derive from arachidonic and eicosapentaenoic acids, respectively. Detailed spectroscopic analysis of the isolated compounds, as natural products and various ester derivatives, afforded the planar structures of seven structurally related constanolactones. Constanolactones A-D possess 1,4-diol functionalities while constanolactones E-G contain a vicinal diol functionality. The absolute stereochemistry at all stereocenters in constanolactones A-D and at two stereocenters in constanolactones E and F were determined by chiral chromatography of fragments and chiroptical measurements of various mono- and dibenzoate derivatives and by comparable rotations within the two series (A-D and E-G). Isolation of these various diastereomeric diols, as well as of two presumed methanol adducts from CHCl3/MeOH extraction of C. simplex, leads us to speculate on the occurrence of highly unstable allylic epoxides in this red alga.
• Intermediacy of 8-(R)-HPETE in the conversion of arachidonic acid to pre-clavulone a by Clavularia viridis. Implications for the biosynthesis of marine prostanoids
  作者：E. J. Corey、Marc D'Alarcao、Seiichi P. T. Matsuda、Peter T. Lansbury、Yasuji Yamada

  DOI：10.1021/ja00235a053

  日期：1987.1
• Synthesis of 12-hydroperoxyeicosatetraenoic acid (12-HPETE). On the stereochemistry in the conversion of 12(S)-HETE to 12-HPETE
  作者：Ryu Nagata、Masayuki Kawakami、Teruo Matsuura、Isao Saito

  DOI：10.1016/s0040-4039(00)99133-0

  日期：——

  12(S)-hydroxyeicosatetraenoic acid methyl ester 1 was synthesized. 1 was converted to phosphite 17 which upon treatment with hydrogen peroxide afforded the corresponding hydroperoxide 18 (12-HPETE methyl ester) with partially retained configuration.

  合成了12（S）-羟基二十碳四烯酸甲酯1。将图1的产物转化为亚磷酸酯17，将其用过氧化氢处理后得到部分保留构型的相应氢过氧化物18（12-HPETE甲酯）。