3-methyl-2-hexenoic acid | 35205-70-0

• 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: 3-methyl-2-hexenoic acid
• 英文别名: 3-methyl-hex-2-enoic acid；3-Methyl-hex-2-ensaeure；β-Methyl-α-amylen-α-carbonsaeure；β-Methyl-β-propyl-acrylsaeure；3-Methyl-hexen-(2)-saeure-(1)；2-Hexenoic acid, 3-methyl-；3-methylhex-2-enoic acid
• CAS: 35205-70-0
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: NTWSIWWJPQHFTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  3
• 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

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-methyl-2-hexenoic acid 在 哌啶 、 溴 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (Z)-2-Bromo-3-methyl-hex-2-enoic acid
  参考文献：
  名称：

  Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition

  摘要：

  An approach to 3-bromo-4-alkyl-6-aryl-5,6-dihydropyridin-2-ones and 3 -bromo-5-ethyl-6-aryl-5,6-dihydropyridin-2-ones starting from beta,gamma-unsaturated alpha-bromoketenes and imines is reported. The presence of a bromine atom on the double bond allows performing aziridination or bromine displacement with an amine. The reaction gave fused bicyclic N-allyl-aziridines or 3-amino-substituted 5,6-dihydropyridin-2-ones, depending on the substituents on the six-membered ring. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.04.021
• 作为产物：
  描述：

  (E)-3-methylhex-2-enenitrile 在 硫酸 作用下， 生成 3-methyl-2-hexenoic acid
  参考文献：
  名称：

  Gardner; Haworth, Journal of the Chemical Society, 1909, vol. 95, p. 1962

  摘要：

  DOI：

文献信息

• Reformatski, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1890, vol. 22, p. 61
  作者：Reformatski

  DOI：——

  日期：——
• Derivatives of Natural Product Agrimophol as Disruptors of Intrabacterial pH Homeostasis in <i>Mycobacterium tuberculosis</i>
  作者：Jie Wu、Ran Mu、Mingna Sun、Nan Zhao、Miaomiao Pan、Hongshuang Li、Yi Dong、Zhaogang Sun、Jie Bai、Minwan Hu、Carl F. Nathan、Babak Javid、Gang Liu

  DOI：10.1021/acsinfecdis.8b00325

  日期：2019.7.12

  This article reports the rational medicinal chemistry of a natural product, agrimophol (1), as a new disruptor of intrabacterial pH (pH(IB)) homeostasis in Mycobacterium tuberculosis (Mtb). Through the systematic investigation of the structure-activity relationship of 1, scaffold-hopping of the diphenylmethane scaffold, pharmacophore displacement strategies, and studies of the structure-metabolism relationship, a new derivative 5a was achieved. Compound 5a showed 100-fold increased potency in the ability to reduce pH(IB) to pH 6.0 and similarly improved mycobactericidal activity compared with 1 against both Mycobacterium bovis-BCG and Mtb. Compound 5a possessed improved metabolic stability in human liver microsomes and hepatocytes, lower cytotoxicity, higher selectivity index, and similar pK(a) value to natural 1. This study introduces a novel scaffold to an old drug, resulting in improved mycobactericidal activity through decreasing pH(IB), and may contribute to the critical search for new agents to overcome drug resistance and persistence in the treatment of tuberculosis.
• Kuhn; Loew, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1939, vol. 259, p. 186
  作者：Kuhn、Loew

  DOI：——

  日期：——
• Sliwa,H.; Maitte,P., Bulletin de la Societe Chimique de France, 1962, p. 369 - 374
  作者：Sliwa,H.、Maitte,P.

  DOI：——

  日期：——
• Kon et al., Journal of the Chemical Society, 1931, p. 1414
  作者：Kon et al.

  DOI：——

  日期：——