(2R,3S)-3-hydroxy-2-methylheptanoic acid | 78944-44-2

• 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,3S)-3-hydroxy-2-methylheptanoic acid
• CAS: 78944-44-2
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: VBFGDSCDTYAEBA-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 、 (2R,3S)-3-hydroxy-2-methylheptanoic acid 在 N-羟基-7-氮杂苯并三氮唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Linfuranones B and C, Furanone-Containing Polyketides from a Plant-Associated Sphaerimonospora mesophila

  摘要：

  Two new furanone-containing polyketides, linfuranones B and C, were isolated from a plant-associated actinomycete of the genus Sphaerimonospora. Their structures were determined by NMR and MS spectroscopic analyses, and the absolute configurations were established by anisotropic methods and chemical degradation approaches. In silico analysis of biosynthetic genes suggested that linfuranone B is generated from linfuranone C by oxidative cleavage of the polyketide chain. Linfuranones B and C induced preadipocyte differentiation into matured adipocytes at 20-40 mu M without showing cytotoxicity.

  DOI：

  10.1021/acs.jnatprod.8b00071
• 作为产物：
  描述：

  (2S)-ethyl N-[2R,3S-(3-hydroxy-2-methylheptanoyl)]-4,4-dimethylpyroglutamate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2R,3S)-3-hydroxy-2-methylheptanoic acid
  参考文献：
  名称：

  Chemoselective Nucleophilic Attack on N-Acyl Derivatives of (S)-Ethyl 4,4-Dimethyl Pyroglutamate (DMPG)

  摘要：

  [GRAPHICS]Heteronucleophiles and C-nucleophiles chemoselectively react with n-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of beta-hydroxy acids likely by formation and ring opening of the corresponding beta-lactones.

  DOI：

  10.1021/ol034847m

文献信息

• Enantioselective aldol condensations. 3. Erythro-selective condensations via zirconium enolates
  作者：D. A. Evans、L. R. McGee

  DOI：10.1021/ja00400a071

  日期：1981.5

  a twisted allene structure 8.'O The loss of activity with increase in temperature further suggests that 8 may rapidly racemize through an intermediate or transition state that can be represented by any of the three structures 6, 11, or 12 or a diradical. Finally, since concerted opening of optically active 8 to 9 should give an active hydrocarbon, 13 was allowed to react with potassium menthoxide in

  扭曲的丙二烯结构 8.'O 随着温度升高而失去活性进一步表明 8 可能通过中间态或过渡态迅速外消旋，该中间态或过渡态可由三种结构 6、11 或 12 中的任何一种或双自由基表示。最后，由于光学活性 8 至 9 的协同打开应产生活性烃，因此在没有呋喃捕集器的情况下，允许 13 与薄荷醇钾反应。不幸的是，9 仅以非常低的产率形成（仅 2-3%；可能是由于在与反应性较低的碱的非常缓慢的反应过程中热稳定性低）。然而，在将其银盐分离并非常彻底地洗涤以去除所有痕量薄荷醇后，形成的少量确实被发现具有光学活性（[.ID2$+2.2 f 0.2'；微池）。
• EVANS, D. A.;MCGEE, L. R., J. AMER. CHEM. SOC., 1981, 103, N 10, 2876-2878
  作者：EVANS, D. A.、MCGEE, L. R.

  DOI：——

  日期：——
• Chemoselective Nucleophilic Attack on <i>N</i>-Acyl Derivatives of (<i>S</i>)-Ethyl 4,4-Dimethyl Pyroglutamate (DMPG)
  作者：Susana Mantecón、Juan J. Vaquero、Julio Alvarez-Builla、María Luz de la Puente、Juan F. Espinosa、Jesús Ezquerra

  DOI：10.1021/ol034847m

  日期：2003.10.1

  [GRAPHICS]Heteronucleophiles and C-nucleophiles chemoselectively react with n-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of beta-hydroxy acids likely by formation and ring opening of the corresponding beta-lactones.
• Linfuranones B and C, Furanone-Containing Polyketides from a Plant-Associated <i>Sphaerimonospora mesophila</i>
  作者：Hirofumi Akiyama、Chantra Indananda、Arinthip Thamchaipenet、Atsuko Motojima、Tsutomu Oikawa、Hisayuki Komaki、Akira Hosoyama、Akane Kimura、Naoya Oku、Yasuhiro Igarashi

  DOI：10.1021/acs.jnatprod.8b00071

  日期：2018.7.27

  Two new furanone-containing polyketides, linfuranones B and C, were isolated from a plant-associated actinomycete of the genus Sphaerimonospora. Their structures were determined by NMR and MS spectroscopic analyses, and the absolute configurations were established by anisotropic methods and chemical degradation approaches. In silico analysis of biosynthetic genes suggested that linfuranone B is generated from linfuranone C by oxidative cleavage of the polyketide chain. Linfuranones B and C induced preadipocyte differentiation into matured adipocytes at 20-40 mu M without showing cytotoxicity.