3-hydroxy-2-methylheptanoic acid

• 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: 3-hydroxy-2-methylheptanoic acid
• 英文别名: (2S,3R)-3-hydroxy-2-methylheptanoic acid
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: VBFGDSCDTYAEBA-NKWVEPMBSA-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 、 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：

  (+/-)-methyl 3-hydroxy-2-methyleneheptanoate 在 palladium on activated charcoal lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 3-hydroxy-2-methylheptanoic acid
  参考文献：
  名称：

  Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis–Hillman adducts. Total synthesis of (±)-sitophilate

  摘要：

  We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00647-0

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：——
• SYNTHESIS OF OLIGOKETIDES
  申请人：Kosan Biosciences

  公开号：EP1144375A2

  公开（公告）日：2001-10-17
• [EN] SYNTHESIS OF OLIGOKETIDES<br/>[FR] SYNTHESE DE POLYCETIDES
  申请人：KOSAN BIOSCIENCES INC

  公开号：WO2000044717A2

  公开（公告）日：2000-08-03

  Facile methods for preparing diketide and triketide thioesters are disclosed. The resulting thioesters may be used as intermediates in the synthesis of desired polyketides, and may contain functional groups which ultimately reside in side chains on the resulting polyketide and thus can be used further to manipulate the polyketide so as to form derivatives. The polyketides produced may also be tailored by glycosylation, hydroxylation and the like. New polyketides and their derivatives and tailored forms are thereby produced.
• Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis–Hillman adducts. Total synthesis of (±)-sitophilate
  作者：Cristiano R Mateus、Melissa P Feltrin、Ana M Costa、Fernando Coelho、Wanda P Almeida

  DOI：10.1016/s0040-4020(01)00647-0

  日期：2001.8

  We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes. (C) 2001 Published by Elsevier Science Ltd.