(E)-methyl 6-hydroxy-4-methylhex-4-enoate | 53585-95-8

• 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: (E)-methyl 6-hydroxy-4-methylhex-4-enoate
• 英文别名: methyl (E)-6-hydroxy-4-methylhex-4-enoate；methyl E-6-hydroxy-4-methyl-4-hexenoate；Methyl-6-hydroxy-4-methylhex-4-enoat
• CAS: 53585-95-8
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: PQOBTUTWNHKPOV-FNORWQNLSA-N

物化性质

• 沸点：
  212.5±28.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  (E)-methyl 6-hydroxy-4-methylhex-4-enoate 在 四溴化碳 、 potassium tert-butylate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 生成 NaQuinate-Me
  参考文献：
  名称：

  ANTICOAGULANT COMPOUNDS AND THEIR USE

  摘要：

  根据该发明提供了一个化合物，其化学式为（I）：其中R1、R2、R3和n的含义如描述中所示，或其药用可接受的溶剂化合物、盐或前药，用作抗凝剂。

  公开号：

  US20180092863A1
• 作为产物：
  描述：

  (E)-6-acetoxy-4-methyl-4-hexenal 在 jones reagent 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 (E)-methyl 6-hydroxy-4-methylhex-4-enoate
  参考文献：
  名称：

  A convergent synthesis of Mycophenolic acid

  摘要：

  A new method for the synthesis of Mycophenolic acid using a convergent approach has been developed where the key step is a palladium mediated allyl-aryl tin coupling. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00061-6

文献信息

• A total synthesis of mycophenolic acid, some analogues and some biogenetic intermediates
  作者：L. Canonica、B. Rindone、E. Santaniello、C. Scolastico

  DOI：10.1016/s0040-4020(01)88962-6

  日期：1972.1

  Mycophenolic acid (28) has been obtained by a convergent synthesis starting from methyl 6-bromo-4-methylhex-4-enoate (13) and 5,7-dihydroxy-4-methylphthalide (24). For the total synthesis of 5,7-dihydroxy-4-methylphthalide, 1-carbethoxy-2,3-dimethylcyclohexa-4,6-dione (14) was aromatized and transformed into 4,6-dimethoxy-2,3-dimethylbenzamide. The photolysis of the corresponding N-chloroamide and

  霉酚酸（28）是通过收敛合成从6-溴-4-甲基己基-4-烯酸甲酯（13）和5,7-二羟基-4-甲基邻苯二甲酸酯（24）开始获得的。为了全合成5,7-二羟基-4-甲基邻苯二甲酰亚胺，将1-碳乙氧基-2,3-二甲基环己-4,6-二酮（14）芳香化并转化为4,6-二甲氧基-2,3-二甲基苯甲酰胺。相应的N-氯酰胺的光解和随后的水解得到5,7-二甲氧基-4-甲基邻苯二甲酸酯，其被水解为5,7-二羟基-4-甲基邻苯二甲酸酯（24）。
• Synthesis, molecular modeling, and evaluation of nonphenolic indole analogs of mycophenolic acid
  作者：Moustafa E El-Araby、Ralph J Bernacki、Gergely M Makara、Paula J Pera、Wayne K Anderson

  DOI：10.1016/j.bmc.2004.03.048

  日期：2004.6

  Based on the promising activity of an indole-3-carboxamide derivative, a nonphenolic analog of mycophenolic acid (MPA), we report herein the synthesis of a compound containing two important features for the activity of MPA, the ring methoxy and methyl. The synthesis was accomplished using two strategies; a method dependent on stepwise building of the hexenoate side chain followed by the indolecarboxamide

  基于吲哚-3-甲酰胺衍生物（霉酚酸（MPA）的非酚类似物）的有前途的活性，我们在此报告了一种化合物的合成，该化合物含有两个重要的MPA活性特征：环甲氧基和甲基。合成使用两种策略完成：一种方法，该方法依赖于己烯酸酯侧链的逐步构建，然后是吲哚羧酰胺环系统，并且依赖于1,3-σ重排的收敛路径是关键步骤。对中国仓鼠和人类II型肌苷单磷酸脱氢酶（IMPDH）的对接实验表明，该化合物与NAD位点具有潜在的结合相互作用。该类似物对MCF7-S，MCF7-R或IGR-OV1癌细胞没有活性。
• Ubiquinone and Related Compounds. XXVII. Synthesis of Urinary Metabolites of Phylloquinone and α-Tocopherol
  作者：MASAZUMI WATANABE、MITSURU KAWADA、MASAO NISHIKAWA、ISUKE IMADA、HIROSHI MORIMOTO

  DOI：10.1248/cpb.22.566

  日期：——

  The syntheses of the metabolites of phylloquinone, α-tocopherol and ubiquinones are described. 1. 2, 3, 5-Trimethyl-6-(3'-carboxybutyl)-1, 4-benzoquinone (VIIa), 2-methyl-3-(3'-carboxybutyl)-1, 4-naphthoquinone (VIIb) and 2, 3-dimethoxy-5-methyl-6-(3'-carboxybutyl)-1, 4-benzoquinone (VIIc) were synthesized by two routes. 2, 3, 5-Trimethylphenol (Ia) and 3-methyl-1-naphthol (Ib) were condensed with methylsuccinic anhydride (II), followed by reduction of the carbonyl groups and oxidation of the phenols to quinones (VIIa, VIIb). 2, 3, 5-Trimethyl-1, 4-benzoquinone (XVIIIa), 2-methyl-1, 4-naphthoquinone (XVIIIb) and 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (XVIIIc) were treated with γ, γ'-dimethoxy-carbonylvaleryl peroxide (XVII) on one step to give the esters (VIIIa, VIIIb, VIIIc) of these quinones. 2. 2, 3, 5-Trimethyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-benzoquinone (XXVa), 2-methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-naphthoquinone (XXVb) and 2, 3-dimethoxy-5-methyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1, 4-benzoquinone (XXVc) were synthesized by boron trifluoride-catalyzed condensation of 2, 3, 5-trimethyl-1, 4-benzohydroquinone (XXIIIa), 2-methyl-1, 4-naphthohydroquinone derivatives (XXIIIb, XXVII, XXVIII) and 2, 3-dimethoxy-5-methyl-1, 4-benzohydroquinone (XXIIIc) with methyl ε-hydroxy-γ-methyl-γ-hexenoate (XX) or methyl γ-hydroxy-γ-vinylvalerate (XXII), followed by hydrolysis of the esters to carboxylic acids and subsequent oxidation of the hydroquinones to quinones.

  描述了叶绿醌、α-生育酚和醌类化合物的代谢物的合成。1. 2, 3, 5-三甲基-6-(3'-羧基丁基)-1, 4-苯醌 (VIIa)、2-甲基-3-(3'-羧基丁基)-1, 4-萘醌 (VIIb) 和2, 3-二甲氧基-5-甲基-6-(3'-羧基丁基)-1, 4-苯醌 (VIIc) 通过两条途径合成。2, 3, 5-三甲基酚 (Ia) 和3-甲基-1-萘醇 (Ib) 与乙基琥珀酸酐 (II) 进行缩合，随后还原羰基基团并将酚氧化为醌 (VIIa, VIIb)。2, 3, 5-三甲基-1, 4-苯醌 (XVIIIa)、2-甲基-1, 4-萘醌 (XVIIIb) 和2, 3-二甲氧基-5-甲基-1, 4-苯醌 (XVIIIc) 在一步中与γ, γ'-二甲氧基-羰基戊酰过氧化物 (XVII) 处理，生成这些醌的酯 (VIIIa, VIIIb, VIIIc)。2. 2, 3, 5-三甲基-6-(5'-羧基-3'-甲基-2'-戊烯基)-1, 4-苯醌 (XXVa)、2-甲基-3-(5'-羧基-3'-甲基-2'-戊烯基)-1, 4-萘醌 (XXVb) 和2, 3-二甲氧基-5-甲基-6-(5'-羧基-3'-甲基-2'-戊烯基)-1, 4-苯醌 (XXVc) 通过三氟化硼催化的缩合反应合成，反应物包括2, 3, 5-三甲基-1, 4-苯醌醇 (XXIIIa)、2-甲基-1, 4-萘醌醇衍生物 (XXIIIb, XXVII, XXVIII) 和2, 3-二甲氧基-5-甲基-1, 4-苯醌醇 (XXIIIc) 与甲基ε-羟基-γ-甲基-γ-己烯酸酯 (XX) 或甲基γ-羟基-γ-乙烯基戊酸酯 (XXII) 反应，随后对酯进行水解生成羧酸，再将醌醇氧化为醌。
• Chiral Amino Alcohol Accelerated and Stereocontrolled Allylboration of Iminoisatins: Highly Efficient Construction of Adjacent Quaternary Stereogenic Centers
  作者：Qiuyuan Tan、Xinqiao Wang、Yang Xiong、Zimeng Zhao、Lu Li、Pei Tang、Min Zhang

  DOI：10.1002/anie.201700581

  日期：2017.4.18

  We have developed a highly efficient asymmetric allylboration of ketimines with nonchiral γ,γ‐disubstituted allylboronic acids by using a chiral amino alcohol as the directing group, which is otherwise challenging. The amino alcohol not only serves as a cheap source of nitrogen and chirality, but also dramatically enhances the reactivity. The versatility of this method was demonstrated by its ability

  我们已经通过使用手性氨基醇作为导向基团开发了一种高效的酮亚胺与非手性γ，γ-二取代的烯丙基硼酸的不对称烯丙基硼酸酯，这在其他方面具有挑战性。氨基醇不仅可以作为氮和手性的廉价来源，而且还可以显着提高反应性。该方法具有多种功能，可通过邻近的季碳中心访问所有四个立体异构体，从而证明了该方法的多功能性。提出了反应模型来解释非对映选择性和速率加速作用。
• [EN] PPAR AGONISTS, COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF<br/>[FR] AGONISTES, COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES PPAR ET MÉTHODES D'UTILISATION DE CEUX-CI
  申请人：MITOBRIDGE INC

  公开号：WO2016057660A8

  公开（公告）日：2016-05-19