(R)-methyl 2,3-dihydroxy-3-methylbutyrate | 37504-90-8

• 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: (R)-methyl 2,3-dihydroxy-3-methylbutyrate
• 英文别名: (R)-α,β-dihydroxyisovaleric methyl ester；(R)-(-)-2,3-Dihydroxy-3-methyl-buttersaeure-methylester；(R)-2,3-dihydroxy-3-methyl-butyric acid methyl ester；methyl (2R)-2,3-dihydroxy-3-methylbutanoate
• CAS: 37504-90-8
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: GHWRZRNYIIZFRP-BYPYZUCNSA-N

物化性质

• 沸点：
  244.2±7.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2,3-dihydroxy-3-methylbutyrate 在 吡啶 、 dimethyl sulfide borane 、 硫酸 、 氨 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 42.0h， 生成 (S)-N-<(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methyl>acetamide
  参考文献：
  名称：

  Eichholzer, John V.; MacLeod, John K., Australian Journal of Chemistry, 1986, vol. 39, # 11, p. 1907 - 1909

  摘要：

  DOI：
• 作为产物：
  描述：

  alpha,beta-二羟基异戊酸 生成 (R)-methyl 2,3-dihydroxy-3-methylbutyrate
  参考文献：
  名称：

  Nielsen; Larsen; Lemmich, Acta Chemica Scandinavica (1947), 1969, vol. 23, # 3, p. 967 - 970

  摘要：

  DOI：

文献信息

• Nielsen; Larsen; Lemmich, Acta Chemica Scandinavica (1947), 1969, vol. 23, # 3, p. 967 - 970
  作者：Nielsen、Larsen、Lemmich

  DOI：——

  日期：——
• Serinolamides and Lyngbyabellins from an <i>Okeania</i> sp. Cyanobacterium Collected from the Red Sea
  作者：Julie G. Petitbois、Loida O. Casalme、Julius Adam V. Lopez、Walied M. Alarif、Ahmed Abdel-Lateff、Sultan S. Al-Lihaibi、Erina Yoshimura、Yasuyuki Nogata、Taiki Umezawa、Fuyuhiko Matsuda、Tatsufumi Okino

  DOI：10.1021/acs.jnatprod.7b00449

  日期：2017.10.27

  NMR-and MS-guided fractionation of an extract of an Okeania sp. marine cyanobacterium, collected from the Red Sea, led to the isolation of four new metabolites, including serinolamides C (1) and D (2) and lyngbyabellins O (3) and P (4), together with the three known substances lyngbyabellins F (5) and G (6) and dolastatin 16 (7). The planar structures of the new compounds were determined using NMR and MS analyses. The absolute configurations of 1 and 2 were determined by Marfey's analysis of their hydrolysates. The absolute configuration of 3 was ascertained by chiral-phase chromatography of degradation products, while that of 4 was determined by comparison to 3 and 5. The cytotoxic and antifouling activities of these compounds were evaluated using MCF7 breast cancer cells and Amphibalanus amphitrite larvae, respectively. Compounds 3, 4, and 7 exhibited strong antifouling activity, and 3 and 7 were not cytotoxic. A structure-activity relationship was observed for the cytotoxicity of the lyngbyabellins with the presence of a side chain (4 is more active than 3) leading to greater activity. For the antifouling activity, the acyclic form without a side chain (3) was the most active.
• Eichholzer, John V.; MacLeod, John K., Australian Journal of Chemistry, 1986, vol. 39, # 11, p. 1907 - 1909
  作者：Eichholzer, John V.、MacLeod, John K.

  DOI：——

  日期：——