1-甲氧基-3-甲基丁-1,3-二烯 | 54717-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-甲氧基-3-甲基丁-1,3-二烯
• 英文名称: 1-methoxy-3-methylbuta-1,3-diene
• 英文别名: 1-methoxy-3-methyl-1, 3-butadiene
• CAS: 54717-57-6
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: CEQACJSYZXQWRM-UHFFFAOYSA-N

物化性质

• 沸点：
  48-50 °C(Press: 30 Torr)
• 密度：
  0.801±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-甲氧基-3-甲基丁-1,3-二烯 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 3-甲基-2-丁烯醛
  参考文献：
  名称：

  Synthetic methods. 15. Unsaturated acyl derivatives of silicon, germanium, and tin from metalated enol ethers

  摘要：

  DOI：

  10.1021/ja00525a019
• 作为产物：
  描述：

  异戊醛 在 sodium trisilicate 、 magnesium monohydrogen phosphate 、 氢氧化钾 、 氯仿 、 氮气 、 溴 作用下， -25.0~350.0 ℃ 、5.33 kPa 条件下， 生成 1-甲氧基-3-甲基丁-1,3-二烯
  参考文献：
  名称：

  Nasarow et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 106,109; engl. Ausg. S. 111, 112

  摘要：

  DOI：

文献信息

• Total Synthesis of the Microtubule-Stabilizing Agent (−)-Laulimalide
  作者：Ian Paterson、Chris De Savi、Matthew Tudge

  DOI：10.1021/ol010150u

  日期：2001.10.1

  [structure: see text] The total synthesis of the potent microtubule-stabilizing anticancer agent (-)-laulimalide has been achieved in 27 steps and 2.9% overall yield. Notable features are the use of Jacobsen HDA chemistry for the enantioselective construction of the side chain dihydropyran, a diastereoselective aldol coupling using chiral boron enolate methodology, a Mitsunobu macrolactonization, and

  [结构：见正文]高效的微管稳定抗癌剂（-）-月桂酰亚胺的总合成已通过27个步骤完成，总产率为2.9％。显着特征是使用Jacobsen HDA化学方法对侧链二氢吡喃进行对映选择性构建，使用手性硼烯醇盐方法进行非对映选择性羟醛偶联，Mitsunobu巨内酯化和Sharpless AE将环氧化物引入去环氧月桂酰亚胺中。
• Asymmetric synthesis of andavadoic acid via base-catalyzed 5-exo-tet cyclization of a β-hydroperoxy epoxide
  作者：Bogdan Barnych、Bernard Fenet、Jean-Michel Vatèle

  DOI：10.1016/j.tet.2012.10.022

  日期：2013.1

  The first total synthesis of andavadoic acid, a naturally occurring five-membered ring peroxide, and its absolute configuration assignment are reported. Central to this venture was the development of an effective synthesis of a key β-hydroperoxy epoxy ester from (R)-epichlorohydrin via chemoselective methylenation with Nysted reagent in the presence of Ti(Oi-Pr)2Cl2 and chemo- and regioselective Mukaiyama–Isayama

  报道了天然存在的五元环过氧化物安达伏酸的第一个全合成及其绝对构型分配。该项目的核心是在（Ti）（O i -Pr）2 Cl 2以及化学和区域选择性的存在下，通过与Nysted试剂进行化学选择性亚甲基化反应，由（R）-表氯醇有效合成关键的β-氢过氧环氧酯。Mukaiyama–Isayama过氧化。该方法还具有通过氢过氧基团通过有效的碱促进的5- exo环氧开口来构造1,2-二氧戊环环系统的特征。
• Total Synthesis of Aphadilactones A–D
  作者：Jian-Peng Yin、Min Gu、Ying Li、Fa-Jun Nan

  DOI：10.1021/jo501117k

  日期：2014.7.3

  The first total synthesis of aphadilactones A-D, diastereomeric natural products recently isolated from the Meliaceae plant Aphanamixis grandifolia by Yue and co-workers, which possess an unprecedented carbon skeleton, has been achieved. The synthesis features a catalytic asymmetric hetero-Diels-Alder reaction to form the dihydropyran ring, concurrent installation of the lactone and furan moieties via a tandem acid-catalyzed acetal cleavage, oxidation, and cyclization process, and an intermolecular Diels-Alder reaction to forge the target products.
• Asymmetric Catalysis of Diels-Alder Cycloadditions by an MS-Free Binaphthol-Titanium Complex: Dramatic Effect of MS, Linear vs Positive Nonlinear Relationship, and Synthetic Applications
  作者：Koichi Mikami、Yukihiro Motoyama、Masahiro Terada

  DOI：10.1021/ja00086a014

  日期：1994.4

  Asymmetric Diels-Alder (D.-A.) reaction of 5-hydroxynaphthoquinone (juglone) with butadienyl acetate catalyzed by the binaphthol-derived chiral titanium (BINOL-Ti) complex 1 proceeds in only 9% ee in the presence of molecular sieves (MS). Remarkably, however, this reaction proceeds in 76-96% ee with BINOL-Ti complex 1 freed from MS to provide the endo-adducts useful for the synthesis of anthracyclines and tetracyclines. The solid MS-free BINOL-Ti complex 1 is stable for months at -20 degrees C, Enhancements in endo selectivity and asymmetric induction are observed with the MS-free BINOL-Ti 1 also in the catalyzed D.-A. cycloaddition of methacrolein and glyoxylate with 1,3-dienol ethers and esters. The glyoxylate adducts can be converted to the mevinolin (compactin) intermediates. Surprisingly, the MS-free complex 1 exhibits not only a linear relationship between the ee's of BINOL-Ti 1 and the D.-A. products but also a positive nonlinear effect (asymmetric amplification), depending simply on the mixing manner of (R)-1 with (S)-1 or (+/-)-1.
• Regiochemical control in the diels alder reactions of substituted naphthoquinones: Orientational manipulation in the synthesis of anthraquinones.
  作者：T.Boss Kelly

  DOI：10.1016/s0040-4039(01)94552-6

  日期：1978.1