(2R,3R,4S)-2,4-dimethyl-3-hydroxyhexanoic acid | 131102-30-2

• 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: (2R,3R,4S)-2,4-dimethyl-3-hydroxyhexanoic acid
• 英文别名: (2R,3R,4S)-3-hydroxy-2,4-dimethylhexanoic acid
• CAS: 131102-30-2
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: DVRYGUNNYGDXGJ-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2,4-dimethyl-3-hydroxyhexanoic acid 在 lithium aluminium tetrahydride 作用下， 生成
  参考文献：
  名称：

  A wittig approach to novel C24 and C25-substituted avermectins.

  摘要：

  DOI：

  10.1016/s0040-4039(00)94434-4
• 作为产物：
  描述：

  2-甲基丁醛 、 rac-2-<(2E)-1-methoxy-2-butenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 生成 (2R*,3R*,4R*)-3-hydroxy-2,4-dimethylhexanoic acid 、 (2R,3R,4S)-2,4-dimethyl-3-hydroxyhexanoic acid
  参考文献：
  名称：

  Hoffmann, Reinhard W.; Dresely, Stefan, Chemische Berichte, 1989, vol. 122, p. 903 - 910

  摘要：

  DOI：

文献信息

• 24- and 25-substituted avermectin and milbemycin derivatives
  申请人：MERCK & CO. INC.

  公开号：EP0428286A2

  公开（公告）日：1991-05-22

  Novel avermectin and milbemycin derivatives are disclosed, where the C-24 and C-25 carbon atoms are substituted by hydrogen, alkyl, alkenyl, substituted alkyl or substituted alkenyl groups. These compounds can be further substituted at the 4˝-, 5-, 13-, and 23-­positions. The new C-24 and C-25 substituted avermectin and milbemycin derivatives are prepared by cleavage of known and suitably protected avermectin and milbemycin compounds. The new compounds are potent anti-parasitic agents, in particular, the compounds are anthelmintic, insecticidal and acaricidal agents.

  公开了新型阿维菌素和米贝霉素衍生物，其中 C-24 和 C-25 碳原子被氢、烷基、烯基、取代烷基或取代烯基取代。这些化合物还可以在 4˝-、5-、13- 和 23-位上被进一步取代。新的 C-24 和 C-25 取代的阿维菌素和米尔贝霉素衍生物是通过裂解已知的并经过适当保护的阿维菌素和米尔贝霉素化合物制备的。这些新化合物是强效的抗寄生虫药剂，特别是具有驱虫、杀虫和杀螨作用。
• Avermectin compounds with a 6,5-spiroketal ring system
  申请人：MERCK & CO. INC.

  公开号：EP0503885A1

  公开（公告）日：1992-09-16

  Avermectin analogs are disclosed wherein the 6,6-spiroketal ring system has been reduced in size to a 6,5-spiroketal ring system by the deletion of the 25-position carbon atom and the 25-alkyl substituent. This is accomplished by opening the outer spiroketal ring with the elimination of ring carbon atoms 23, 24 and 25 and the alkyl substituent at the 25-position and incorporation a new component, reclosing the spiroketal to a 5-membered ring with new substituents at the 24-position. The compounds are used as anti-parasitic insecticidal and anti-helmintic agents in humans and animals and compositions containing such compounds as the active ingredient thereof are also disclosed.

  本发明公开了阿维菌素类似物，通过删除 25 位碳原子和 25 位烷基取代基，6,6-螺酮环系的体积缩小为 6,5- 螺酮环系。具体做法是通过消除环碳原子 23、24 和 25 以及 25 位上的烷基取代基来打开螺酮醛外环，并加入一个新的成分，从而将螺酮醛重新封闭成一个 5 元环，并在 24 位上加入新的取代基。这些化合物可用作人类和动物的抗寄生虫杀虫剂和抗蠕虫剂，还公开了以这些化合物为活性成分的组合物。
• 4"-and 4'-alkylthio-avermectin derivatives
  申请人：MERCK & CO. INC.

  公开号：EP0506331A1

  公开（公告）日：1992-09-30

  Avermectin derivatives are disclosed wherein the 4˝-hydroxy group is replaced by a substituted alkylthio or acylthio group or an iodo group. These avermectin derivatives can be further derivatized at the 5- and 23-positions as ketoximes or O-substituted ketoximes. The 4˝-substituted avermectin derivatives are prepared from the 4˝- and 4′-trifluoromethanesulfonyl avermectin derivatives with halo- or sulfur-containing nucleophiles. The 4˝- and 4′-α-and β-trifluoromethane sulfonates are prepared selectively and converted into 4˝- or 4′-alkyl- or acylsulfides, or iodides using the appropriate sulfur-containing or iodine nucleophile. Substituted sulfoxy and sulfonyl substituents at the 4˝- and 4′-positions are prepared from oxidation of the corresponding substituted sulfides. The new compounds are potent anti-parasitic agents; in particular, the compounds are anthelmintic, insecticidal and acaricidal agents.

  已公开的阿维菌素衍生物中，4˝-羟基被取代的烷硫基或酰硫基或碘基所取代。这些阿维菌素衍生物可在 5-位和 23-位进一步衍生为酮肟或 O-取代酮肟。4˝ 取代的阿维菌素衍生物是由 4˝- 和 4′-三氟甲磺酰基阿维菌素衍生物与卤代或含硫亲核物制备而成。选择性地制备 4˝-和 4′-α-和 β-三氟甲烷磺酸盐，并使用适当的含硫或碘亲核剂将其转化为 4˝-或 4′-烷基或酰基硫化物或碘化物。在 4˝-和 4′-位置上的取代的磺氧基和磺酰基是通过氧化相应的取代的硫化物制备的。这些新化合物是强效的抗寄生虫剂，尤其是具有驱虫、杀虫和杀螨作用。
• Cleavage of the spiroketal portion of avermectin B2a
  作者：Thomas L. Shih、Helmut Mrozik、Mark A. Holmes、Michael H. Fisher

  DOI：10.1016/s0040-4039(00)94433-2

  日期：1990.1
• Avermectin compounds with a 6,5-spiroketal ring system and a 23-acyl substituent
  申请人：Merck & Co., Inc.

  公开号：EP0537996B1

  公开（公告）日：1998-01-07