2-己烯-1-醇,6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-3-甲基-,(E)- | 100045-81-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 2-己烯-1-醇,6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-3-甲基-,(E)-
• 英文名称: (E)-3-methyl-6-<(tert-butyldimethylsilyl)oxy>-2-hexen-1-ol
• 英文别名: 6-<(tert-butyldimethylsilyl)oxy>-3-methyl-2(E)-hexen-1-ol；(E)-6-((tert-butyldimethylsilyl)oxy)-3-methylhex-2-en-1-ol；(E)-6-(tert-butyldimethylsilanyloxy)-3-methylhex-2-en-1-ol；(2E)-6-tert-butyldimethylsilyloxy-3-methyl-2-hexen-1-ol；(E)-6-(tert-butyldimethylsiloxy)-3-methyl-2-hexen-1-ol；(E)-6-O-tert-butyldimethylsilyl-3-methyl-2-hexene-1-ol；(E)-6-[tert-butyl(dimethyl)silyl]oxy-3-methylhex-2-en-1-ol
• CAS: 100045-81-6
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: XGOYTMHUCZBCEA-FMIVXFBMSA-N

物化性质

• 沸点：
  292.5±28.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-己烯-1-醇,6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-3-甲基-,(E)- 在 盐酸 、 正丁基锂 、 jones reagent 、 dilithium tetrachlorocuprate 、 甲基锂 、 溴 、 叔丁基锂 、 甲基磺酰氯 、 叔丁胺 、 lithium bromide 作用下， 以 甲醇 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 35.42h， 生成 霉酚酸
  参考文献：
  名称：

  霉酚酸的全合成

  摘要：

  这些合成 a partir de t-丁基二甲基甲硅烷氧基-8 (=R-8) 甲氧基-1 甲基-5 辛烯-4yne-1 和去甲氧基甲氧基甲基-3 (=R'-3) 甲基-2 环丁烯-2one-1 通过环化 de l' 酸 R-3 R'-6 羟基-2 甲氧基-4 甲基-5 苯甲酸

  DOI：

  10.1021/ja00264a038
• 作为产物：
  描述：

  (E)-tert-butyl((5-iodo-4-methylpent-4-en-1-yl)oxy)dimethylsilane 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.83h， 生成 2-己烯-1-醇,6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-3-甲基-,(E)-
  参考文献：
  名称：

  Synthesis of Sulfur- and Sulfoxide-Substituted 2,3-Oxidosqualenes and Their Evaluation as Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  2,3-Oxidosqualene (23-OS) analogs that contain thioether (52-55) and sulfoxide (56-60) at positions normally occupied by carbons considered to be cationic during 2,3-oxidosqualene-lanosterol cyclase (OSC) cyclization (C-6, C-10, C-14, and C-19) were synthesized and tested as substrate mimic inhibitors of fungal and mammalian OSC. The analogs were found to be potent inhibitors of cyclase in cell-free extracts of Candida albicans and rat liver. Thioether analogs were more potent than the corresponding sulfoxides. In both series, those 2,3-OS analogs containing a sulfur at the position normally occupied by C-19 were the most potent. With C. albicans cyclase, the IC50 for thioether 55 was 0.0023 mu M while 60 exhibited an IC50 of 0.065 mu M, which are the lowest values reported for a inhibitor of this enzyme. Similarly, thioether 55 displayed an IC50 of 0.00082 mu M for rat liver cyclase which is the best inhibitor up to date for this enzyme. These results suggest that mimics with modification in the region of C-19 of 2,3-OS have a high affinity for the active site of these enzymes. The same series of analogs (52-60) were also tested for inhibition of cholesterol biosynthesis in intact MDBK (Madin Darbin bovine kidney) cells and for in vitro antifungal activity against C. albicans.

  DOI：

  10.1021/ja00107a011

文献信息

• Synthetic routes to cristatic acid and derivatives
  作者：Jack Chiarello、Madeleine M. Joullié

  DOI：10.1016/s0040-4020(01)85090-0

  日期：1988.1

  Synthetic paths to cristatic acid derivatives are explored and a convergent route to the total synthesis of these molecules is described.

  探索了到环戊酸衍生物的合成途径，并描述了这些分子全部合成的收敛途径。
• Synthesis and Liver Microsomal Metabolic Stability Studies of a Fluorine‐Substituted δ‐Tocotrienol Derivative
  作者：Xingui Liu、Saikat Poddar、Lin Song、Howard Hendrickson、Xuan Zhang、Yaxia Yuan、Daohong Zhou、Guangrong Zheng

  DOI：10.1002/cmdc.201900676

  日期：2020.3.18

  A fluoro-substituted δ-tocotrienol derivative, DT3-F2, was synthesized. This compound was designed to stabilize the metabolically labile terminal methyl groups of δ-tocotrienol by replacing one C-H bond on each of the two methyl groups with a C-F bond. However, in vitro metabolic stability studies using mouse liver microsomes revealed an unexpected rapid enzymatic C-F bond hydrolysis of DT3-F2. To

  合成了氟取代的δ-生育三烯酚衍生物DT3-F2。该化合物被设计为通过用CF键取代两个甲基上每个的一个CH键来稳定δ-生育三烯酚的代谢不稳定的甲基。但是，使用小鼠肝微粒体进行的体外代谢稳定性研究表明，DT3-F2发生了意外的快速酶促CF键水解。据我们所知，这是烯丙基CF键异常代谢水解的第一个报道。
• Synthetic studies towards the phomactins. Concise syntheses of the tricyclic furanochroman and the oxygenated bicyclo[9.3.1]pentadecane ring systems in phomactin A
  作者：Kevin M Foote、Christopher J Hayes、Matthew P John、Gerald Pattenden

  DOI：10.1039/b307985f

  日期：——

  A concise synthesis of the tricyclic furanochroman unit 3 found in the PAF antagonist phomactin A (1) isolated from the marine fungus Phoma sp., is described. In complementary studies, a variety of synthetic routes towards the bicyclo[9.3.1]pentadecane ring system 4 in phomactin A were explored. These studies culminated in a synthesis of the substituted ring system 79 containing all the carbon atoms

  描述了从海洋真菌Phoma sp。分离出的PAF拮抗剂phomactin A（1）中发现的三环呋喃喃喃单元3的简明合成。在补充研究中，探索了多种在光蛋白A中合成双环[9.3.1]十五烷环系统4的合成途径。这些研究最终合成了取代环系统79，该取代环系统包含所有的碳原子和所有必要的氧中心，以形成光蛋白A本身。
• Cembranolide total synthesis. Anisomelic acid
  作者：James A. Marshall、Bradley S. DeHoff

  DOI：10.1016/s0040-4020(01)87668-7

  日期：1987.1

  synthesis of (±)-anisomelic acid (34) has been achieved starting from aldehyde 7, the ozonolysis product of geranyl acetate. Two key steps ensured the stereoselectivity of the synthesis. The first entailed a highly anti-selective addition of the allyltitanium derived from carbamate 15 to aldehyde 5 affording the enol carbamate allylic alcohol 16. The second was a highly (Z)-selective Horner-Emmons cyclization

  （±）-茴香酸（34）的立体选择性全合成反应是从醛香叶酸乙酸香叶酯的臭氧分解产物醛7开始的。两个关键步骤确保了合成的立体选择性。首先需要将来自氨基甲酸酯15的烯丙基钛高度反选择性地添加到醛5中，得到烯醇氨基甲酸酯烯丙基醇16。第二个是衍生的膦酰基酯醛25的高度（Z）选择性霍纳-埃蒙斯环化反应，产生共轭酯27。进一步转化产生结晶内酯30通过单晶X射线分析证实了其结构。30的共轭双键的平衡产生（Z）和（E）异构体的1：1混合物。分子力学计算预言了这一结果。
• A Synthetic Study on Antiviral and Antioxidative Chromene Derivative
  作者：Jun Mori、Makoto Iwashima、Makoto Takeuchi、Haruo Saito

  DOI：10.1248/cpb.54.391

  日期：——

  An efficient synthesis of the antiviral and antioxidative chromene (1) was achieved. A small amount of chromene 1 could be derived from plastoquinones 2 and 3, the major constituents of the brown alga, Sargassum micracanthum. By the following synthetic scheme involving its application, many kinds of analogs can be synthesized for evaluation of their biological activity and mechanistic study. The total

  实现了抗病毒和抗氧化色烯 (1) 的有效合成。少量色烯 1 可能源自质体醌 2 和 3，它们是褐藻马尾藻的主要成分。通过以下涉及其应用的合成方案，可以合成多种类似物，用于评价其生物活性和机理研究。 1的全合成以乙酸香叶酯和受保护的2-溴-6-甲基氢醌为起始原料，采用Sharpless不对称二羟基化引入末端二醇体系和碱催化σ重排构建色烯骨架作为关键步骤。通过该合成再次确认了 C-11' 处的立体化学。