2-methylhex-5-enoic acid | 77290-89-2

• 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: 2-methylhex-5-enoic acid
• 英文别名: 2-methyl-5-hexenoic acid；2-Methyl-hexen-(5)-saeure
• CAS: 77290-89-2
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: SXUXAXVRKXYXQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 1.5 Torr)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylhex-5-enoic acid 在 rhodium⁽²⁺⁾ 氯甲酸甲酯 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 生成 2,6-methano-3a-methyl-6a-phenyl-3,3a,4,5,6,6a-hexahydro-2H-cyclopentafuran-3-one
  参考文献：
  名称：

  Ligand-Induced Selectivity in the Rhodium(II)-Catalyzed Reactions of α-Diazo Carbonyl Compounds

  摘要：

  3-Allyl-2,5-diazopentanedione and 3-butenyl-2,5-diazopentanedione were allowed to react with a trace amount of a rhodium(II) catalyst in methylene chloride at room temperature. The major products isolated correspond to the internal trapping of a carbonyl ylide as well as intramolecular cyclopropanation. Changing the catalyst from Rh-2(OAc)(4) to Rh-2(cap)(4) to Rh-2(tfa)(4) caused a significant alteration in product distribution. A rather unusual and unexpected regiochemical crossover in the cycloaddition occurred when Rh-2(tfa)(4) was used and is most likely due to complexation of the metal with the dipole. A computational approach to rationalize the observed product distribution was carried out. The thermodynamic stabilities of cycloaddition transition states were approximated from the computationally derived strain energies of ground state molecules using traditional force-field techniques. Globally minimized ground state energies were obtained for all possible cycloaddition products, and final strain energies were calculated. In all cases studied, the lower energy isomer corresponded to the cycloadduct actually isolated. A study of the regiochemical aspects of the Rh(II)-catalyzed reaction of 1-diazo-3-(2-oxo-2-phenylethyl)hexane-2, was also carried out. Cyclization of the initially formed rhodium carbenoid occurred exclusively across the acetyl rather than the benzoyl group. The structure of the internal cycloadduct was assigned on the basis of a proton-detected multiple-bond heteronuclear multiple-quantum coherence experiment.

  DOI：

  10.1021/jo951576n
• 作为产物：
  描述：

  2-甲基-5-己烯-1-醛 在 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 乙腈 为溶剂， 以78%的产率得到2-methylhex-5-enoic acid
  参考文献：
  名称：

  N-杂环碳合作用（NHC）和钌氧化还原催化：以空气为末端氧化剂的醛的氧化酯化反应

  摘要：

  本文描述了一种NHC（N-杂环卡宾）和基于钌的氧化还原配合催化，用于各种芳香族和杂芳香族醛的轻度好氧氧化酯化。钌（II）络合物Ru（bpz）3（PF 6）2（bpz = 2,2'-联吡嗪）作为催化剂可与游离NHC相容。在这些级联反应中，将NHC用于醛的缩聚反应，以形成相应的Breslow中间体，该中间体又被钌氧化还原催化剂氧化为酰基zo离子。空气用作钌催化剂氧化（再生）的终端氧化剂。此外，我们将表明，在不存在钌氧化还原催化剂和醇的情况下，NHC催化的醛的好氧氧化可提供相应的酸，收率很好。提供了支持我们建议机制的机理研究和DFT计算。

  DOI：

  10.1002/adsc.201300034

文献信息

• Ethylenic acyl cyanides I.: conjugate addition of allyl and allenylsilanes to ethylenic acyl cyanides.
  作者：Abdelkebir Jellal、Maurice Santelli

  DOI：10.1016/s0040-4039(00)74530-8

  日期：1980.1

  δ,ε-Ethylenic (or acetylenic) acyl cyanides, or δ,ε-ethylenic (or acetylenic) acids and their methyl esters, can be obtained by a conjugate addition of allyl (or allenyl) silanes to α,β-ethylenic acyl cyanides.

  δ，ε-乙烯（或炔属）酰基氰化物或δ，ε-乙烯（或炔属）酸及其甲酯可通过将烯丙基（或烯丙基）硅烷共轭加成至α，β-乙烯酰基氰化物而制得。
• Arginase Inhibitors and Their Therapeutic Applications
  申请人：OncoArendi Therapeutics S.A.

  公开号：US20170319536A1

  公开（公告）日：2017-11-09

  Disclosed are small molecule therapeutic compounds that are potent inhibitors of arginase 1 and arginase 2 activity. Also disclosed are pharmaceutical compositions comprising the compounds, and methods for using the compounds for treating or preventing a disease or condition associated with arginase activity.

  揭示了一种小分子治疗化合物，它们是较强的精氨酸酶1和精氨酸酶2活性抑制剂。还揭示了包含这些化合物的药物组合物，以及使用这些化合物治疗或预防与精氨酸酶活性相关的疾病或状况的方法。
• A facile method for synthesis of three carbon-homologated carboxylic acid by regioselective ring-opening of β-propiolactones with organocopper reagents
  作者：Masatoshi Kawashima、Toshio Sato、Tamotsu Fujisawa

  DOI：10.1016/0040-4020(89)80068-7

  日期：——

  β-carbon-oxygen fission to give 3-substituted propionic acids. Among these three kinds of organocopper reagents, diorganocuprate, especially halomagnesium cuprate gave the highest yields of the acids, which was remarkably observed in the ring-opening of sterically hindered β-propiolactones such as β-methyl- and α,β -dimethyl-β-propiolactones and also in the reactions using the organocopper reagents with vinyl and

  在铜（I）盐存在下，有机铜试剂，例如二有机铜酸盐，有机铜-三丁基膦和格利雅试剂，通过区域选择性的β-碳-氧裂变与β-丙内酯反应，生成3-取代的丙酸。在这三种有机铜试剂中，二有机铜酸盐，特别是铜卤化铝的酸收率最高，这在空间受阻的β-丙内酯（如β-甲基-和α，β-二甲基-β）的开环中表现得尤为明显。 -丙内酯，以及在使用带有铜和烯丙基取代基的有机铜试剂的反应中。S N证实β-丙内酯开环通过顺式-α，β-二甲基-β-丙内酯与二叔丁基杯酸酯的反应，β-碳的构型主要转化的2通路，得到syn-2,3,4,4-四甲基戊酸。
• Regioselective Silver-Mediated Kondakov-Darzens Olefin Acylation
  作者：Nicholas T. Barczak、Elizabeth R. Jarvo

  DOI：10.1002/chem.201102476

  日期：2011.11.11

  Enone construction: A silver‐mediated olefin acylation reaction is described, in which five‐, six‐, and ‐seven‐membered rings, tetrasubstituted olefins, bridged bicycles, spirocycles, and benzoxepinones are prepared. Highly selective intermolecular reactions are coupled to a Nazarov cyclization for the effective preparation of cyclopentenones, including the core of modhephene (see scheme).

  烯酮的结构：描述了一种银介导的烯烃酰化反应，其中制备了五元，六元和七元环，四取代的烯烃，桥连的自行车，螺环和苯并庚二酮。高度选择性的分子间反应与Nazarov环化反应相结合，可有效制备环戊烯酮，包括莫非芬的核心（参见方案）。
• Method for producing anellated tetrahydro-{1h}-triazoles
  申请人：——

  公开号：US20040097728A1

  公开（公告）日：2004-05-20

  The present invention relates to a process for preparing fused tetrahydro-[ 1 H]-triazoles of the formula I 1 where the variables R a , Z, Z 1 , X, W, n and Q are as defined in claim 1, by cyclization of compounds of the formula II 2 where R is C(X)OR 2 or C(X)SR 2 , where X is oxygen or sulfur, and R 2 is as defined in claim 1, in the presence of a base. The invention also relates to compounds of the formula I where W is sulfur if Z is a methylene group optionally substituted by R a , and furthermore to compounds of the formula I where Q is a benzoxazole or benzothiazole radical, and to the use of these compounds as herbicides.

  本发明涉及一种制备公式I的熔融四氢咪唑的方法，其中变量Ra、Z、Z1、X、W、n和Q如权利要求1中定义，通过在碱存在下，将公式II的化合物环化得到，其中R为C(X)OR2或C(X)SR2，其中X为氧或硫，R2如权利要求1中定义。该发明还涉及公式I的化合物，其中如果Z是可选地由Ra取代的亚甲基基团，则W为硫，此外还涉及公式I的化合物，其中Q为苯并噁唑或苯并噻唑基团，并将这些化合物用作除草剂。