(R)-3,7-dimethyloct-2E-en-1,6,7-triol | 63955-79-3

• 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)-3,7-dimethyloct-2E-en-1,6,7-triol
• 英文别名: (E, R)-3,7-dimethyl- oct-2-ene-1,6,7-triol；(E,6R)-3,7-dimethyloct-2-ene-1,6,7-triol
• CAS: 63955-79-3
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: FBAPOIPDUVYEKZ-BNICOGTQSA-N

物化性质

• 沸点：
  345.6±42.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3,7-dimethyloct-2E-en-1,6,7-triol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 18.0h， 生成 (E, R)-3-methyl-5-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl) pent-2-enoic acid
  参考文献：
  名称：

  6,7-二羟基-3,7-二甲基辛-2-烯酸的四个异构体，酯的不同合成及其抗真菌活性的评价

  摘要：

  摘要以香叶醇的选择性直接Sharpless不对称二羟基化为关键步骤，合成了6,7-二羟基-3,7-二甲基辛-2-烯酸2的四个异构体，这是提高总收率35.0％至48.0％，91.9％至97.7的关键步骤以顺式和反式香叶醇为原料，酯4的ee值％和总收率的31.3％– 36.4％，酸2的ee值为90.3–97.5％。它们的结构通过1 H，13 C NMR和HR-ESI-MS数据表征。体内生物测定结果表明，手性酸（Z，S）-2是一种良好的先导化合物，在浓度为5％时，对立方霉菌，格氏大肠杆菌，高粱和球孢梭菌具有80％-100％的抑制率。 400微克/毫升

  DOI：

  10.1016/j.cclet.2018.02.006
• 作为产物：
  描述：

  三十碳六烯-2,3-二醇 生成 (R)-3,7-dimethyloct-2E-en-1,6,7-triol
  参考文献：
  名称：

  Boar; Damps, Journal of the Chemical Society. Perkin transactions I, 1977, # 6, p. 709 - 712

  摘要：

  DOI：

文献信息

• Study of the regio- and enantioselectivity of the reactions of osmium tetroxide with allylic alcohols and allylic sulfonamides
  作者：Daqiang Xu、Christine Y. Park、K.Barry Sharpless

  DOI：10.1016/s0040-4039(00)77153-x

  日期：1994.4

  geranyl sulfonamides suggest the presence of a moderate attractive interaction between OsO4 and the allylic groups bearing acidic protons. This allylic directing effect may be due to the development of a hydrogen bonding interaction between OsO4 and the substrates during the osmylation process. The potential for a hydrogen bond can also have a substantial effect on the enantioselectivities of the osmium

  香叶醇，其衍生物和香叶基磺酰胺酰胺化的区域选择性表明，OsO 4与带有酸性质子的烯丙基之间存在适度的吸引作用。这种烯丙基导向作用可能归因于在osmylation过程中OsO 4与底物之间的氢键相互作用的发展。氢键的潜力还可对四氧化os催化的烯丙醇的不对称二羟基化的对映选择性产生实质性影响。
• Chemo-enzymatic enantio-convergent asymmetric synthesis of (R)-(+)-Marmin
  作者：Klaus Edegger、Sandra F Mayer、Andreas Steinreiber、Kurt Faber

  DOI：10.1016/j.tet.2003.10.106

  日期：2004.1

  Asymmetric biohydrolysis of trisubstituted terpenoid oxiranes (rac-1a–rac-3a) was accomplished by employing the epoxide hydrolase activity Rhodococcus and Streptomyces spp. Depending on the biocatalyst, the biohydrolysis proceeded in an enantio-convergent fashion and gave the corresponding vic-diols in up to 97% ee at conversions beyond the 50%-threshold. In order to avoid a depletion of the ee of

  三取代萜类化合物肟（rac - 1a – rac - 3a）的不对称生物水解是通过利用环氧化酶活性红球菌和链霉菌属（Streptomyces spp ）来完成的。取决于生物催化剂，所述biohydrolysis在对映会聚方式进行，并且得到相应的VIC在高达97％的ee值-diols在50％ -阈值超出转换。为了避免通过进一步的氧化代谢耗尽产物的ee，必须在惰性气氛中排除分子氧进行生物转化。单萜类香豆素的不对称全合成证明了该方法的合成适用性（R）-（+）-Marmin在95％ee中。
• Monoterpenoid Glycosides from the Leaves of Ligustrum robustum and Their Bioactivities (II)
  作者：Shi-Hui Lu、Xiu-Xia Li、Hao-Jiang Zuo、Wei-Neng Li、Jia-Ping Pan、Jing Huang

  DOI：10.3390/molecules28217274

  日期：——

  Ligustrum robustum has been not only used as a heat-clearing and detoxicating functional tea (Ku-Ding-Cha) but also consumed as a hypotensive, anti-diabetic, and weight-reducing folk medicine. From the leaves of L. robustum, ten new monoterpenoid glycosides named ligurobustosides T10 (1a), T11 (1b), T12 (2a), T13 (2b), T14 (3a), T15 (3b), F1 (4b), T16 (5a), T17 (5b), and E1 (6b), together with five known ones (4a, 6a, 7, 8a, 8b), were separated and identified using the spectroscopic method and chemical method in this research. The results of biological tests exhibited that the fatty acid synthase (FAS) inhibitory action of compound 5 (IC50: 4.38 ± 0.11 μM) was as strong as orlistat (IC50: 4.46 ± 0.13 μM), a positive control; the α-glucosidase inhibitory actions of compounds 1–4 and 7–8, and the α-amylase inhibitory actions of compounds 1–8 were medium; the ABTS radical scavenging capacities of compounds 1–3 and 5–8 (IC50: 6.27 ± 0.23 ~ 8.59 ± 0.09 μM) were stronger than l-(+)-ascorbic acid (IC50: 10.06 ± 0.19 μM) served as a positive control. This research offered a theoretical foundation for the leaves of L. robustum to prevent diabetes and its complications.

  女贞不仅被用作清热解毒的功能茶（古丁茶），还被用作降血压、抗糖尿病和减轻体重的民间药物。从L.本研究采用光谱法和化学法，从粗壮草叶中分离并鉴定了十种新的单萜苷，分别命名为女贞苷 T10（1a）、T11（1b）、T12（2a）、T13（2b）、T14（3a）、T15（3b）、F1（4b）、T16（5a）、T17（5b）和 E1（6b），以及五种已知的单萜苷（4a、6a、7、8a、8b）。生物学试验结果表明，化合物 5（IC50：4.38 ± 0.11 μM）对脂肪酸合成酶（FAS）的抑制作用与奥利司他（IC50：4.46 ± 0.13 μM）；化合物1-4和7-8的α-葡萄糖苷酶抑制作用和化合物1-8的α-淀粉酶抑制作用均为中等；化合物1-3和5-8的ABTS自由基清除能力（IC50：6.27 ± 0.23 ~ 8.59 ± 0.09 μM）强于作为阳性对照的l-(+)-抗坏血酸（IC50：10.06 ± 0.19 μM）。这项研究为健壮叶预防糖尿病及其并发症提供了理论依据。
• Postulated Biogenesis of WS9885B and Progress toward an Enantioselective Synthesis
  作者：Christopher D. Vanderwal、David A. Vosburg、Sven Weiler、Erik J. Sorensen

  DOI：10.1021/ol990723r

  日期：1999.8.1

  WS9885B promotes the assembly of microtubules in vitro and displays cytotoxicity as potent as paclitaxel against several cancer cell lines. In this Letter, we propose a biogenesis for this architecturally complex bacterial metabolite from a much simpler, polyunsaturated precursor. We also present significant progress toward a convergent, enantioselective synthesis of WS9885B, Our work features a chemoselective palladium-catalyzed cross coupling of two advanced building blocks and an uncommon Claisen-like cyclization.
• Bioactive constituents from the leaves of Metapanax delavayi with anti-benign prostatic hyperplasia activities
  作者：Bangjian Dong、Chongzhi Sun、Mengyue Wang、Feng Liu、Xiaobo Li

  DOI：10.1016/j.phytochem.2021.112979

  日期：2022.1