(1Z,3Z)-1,4-二甲氧基-1,3-丁二烯 | 83650-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1Z,3Z)-1,4-二甲氧基-1,3-丁二烯
• 英文名称: (1Z,3Z)-1,4-dimethoxy-1,3-butadiene
• 英文别名: 1,3-Butadiene, 1,4-dimethoxy-, (Z,Z)-；(1Z,3Z)-1,4-dimethoxybuta-1,3-diene
• CAS: 83650-30-0
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: ZFOMGKMTIIJRAI-GLIMQPGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 1t,4t-dimethoxy-buta-1,3-diene 、 (1Z,3Z)-1,4-二甲氧基-1,3-丁二烯 、 (1Z, 3E)-1,4-dimethoxy-1,3-butadiene 在 1-间苯磺酸钠基-5-巯基-1H-四氮唑 作用下， 反应 5.0h， 以62%的产率得到1,1,4,4-tetramethoxy-2-butene
  参考文献：
  名称：

  Process for Preparing 1,1,4,4-Tetraalkoxybut-2-Ene Derivatives

  摘要：

  制备通式（I）中的1,1,4,4-四烷氧基丁-2-烯衍生物的过程，其中基团R1和R2各自独立地为氢、C1-C6烷基、C6-C12芳基（例如苯基）或C5-C12环烷基，或者基团R1和R2与它们所结合的双键共同形成C6-C12芳基基团（例如苯基），该苯基基团被一个或多个C1-C6烷基、卤素原子或烷氧基取代，或者是单不饱和或多不饱和的C5-C12环烷基基团，R3和R4各自独立地为氢、甲基、三氟甲基或腈基。该过程包括在C1-C6烷基醇的存在下，电化学氧化通式（II）中的1,4-二烷氧基-1,3-丁二烯，其中基团R1、R3和R4的含义与通式（I）中的相同。

  公开号：

  US20080228009A1
• 作为产物：
  描述：

  E-4-bromobut-2-enal dimethyl acetal 在 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 4.25h， 生成 (1Z,3Z)-1,4-二甲氧基-1,3-丁二烯
  参考文献：
  名称：

  Stereocontrolled Synthesis and Cycloaddition of 1,4-Dialkoxy 1,3-Dienes

  摘要：

  An efficient and stereocontrolled access to 1(Z),3(E)-1,4-dialkoxybutadienes is described that relies on a base-induced conjugated elimination reaction on y-alkoxy or aryloxy a,a-unsaturated acetals. The dienes have then been applied in [4 + 2] cycloaddition reactions where they demonstrate a good thermal reactivity toward activated dienophiles. Despite the 1,4-competition between oxygenated groups, both regio- and endoselectivities are total. A set of experiments has led to the conclusion that the (1Z,3E) pattern is responsible for these high stereocontrols. Several chiral alkoxy dienes have also been prepared following the same route. Their thermal cycloaddition with N-methylmaleimide leads to corresponding adducts in good yields and with total endoselectivities, but modest diastereoisomeric excess.

  DOI：

  10.1021/jo980321h

文献信息

• Additions of singlet oxygen to alkoxy-substituted dienes. The mechanism of the singlet oxygen 1,2-cycloaddition reaction
  作者：Edward L. Clennan、Krzysztof. Nagraba

  DOI：10.1021/ja00221a034

  日期：1988.6

  Les reactions de l'oxygene singulet avec les stereoisomeres du dimethoxy-1,4 butadiene-1,3 donnent majoritairement les (methoxy-3 methoxy-2' vinyl-4) dioxetannes-1,2 correspondants

  Les reactor de l'oxygene singulet avec lesstereoisomeres du di 二甲氧基-1,4 butadiene-1,3 donnent Majoritairement les (甲氧基-3 甲氧基-2'乙烯基-4) 二氧杂环丁烷-1,2 对应物
• 1,4-Dimethoxy-1,3-butadiene as a donor diene in Diels-Alder cycloadditions
  作者：Hidetoshi Hiranuma、Sidney I. Miller

  DOI：10.1021/jo00147a007

  日期：1982.12
• Stereocontrolled Synthesis and Cycloaddition of 1,4-Dialkoxy 1,3-Dienes
  作者：Anne Guillam、Loïc Toupet、Jacques Maddaluno

  DOI：10.1021/jo980321h

  日期：1998.7.1

  An efficient and stereocontrolled access to 1(Z),3(E)-1,4-dialkoxybutadienes is described that relies on a base-induced conjugated elimination reaction on y-alkoxy or aryloxy a,a-unsaturated acetals. The dienes have then been applied in [4 + 2] cycloaddition reactions where they demonstrate a good thermal reactivity toward activated dienophiles. Despite the 1,4-competition between oxygenated groups, both regio- and endoselectivities are total. A set of experiments has led to the conclusion that the (1Z,3E) pattern is responsible for these high stereocontrols. Several chiral alkoxy dienes have also been prepared following the same route. Their thermal cycloaddition with N-methylmaleimide leads to corresponding adducts in good yields and with total endoselectivities, but modest diastereoisomeric excess.
• Process for Preparing 1,1,4,4-Tetraalkoxybut-2-Ene Derivatives
  申请人：Richter Ingo

  公开号：US20080228009A1

  公开（公告）日：2008-09-18

  Process for preparing 1,1,4,4-tetraalkoxybut-2-ene derivatives of the general formula (I), where the radicals R 1 and R 2 are each, independently of one another, hydrogen, C 1 -C 6 -alkyl, C 6 -C 12 -aryl, such as phenyl, or C 5 -C 12 -cycloalkyl or R 1 and R 2 together with the double bond to which they are bound form a C 6 -C 12 -aryl radical, such as phenyl, a phenyl radical substituted by one or more C 1 -C 6 -alkyl groups, halogen atoms or alkoxy groups or a monounsaturated or polyunsaturated C 5 -C 12 -cycloalkyl radical, R 3 , R 4 are each, independently of one another, hydrogen, methyl, trifluoromethyl or nitrile, which comprises electrochemically oxidizing 1,4-dialkoxy-1,3-butadiene of the formula II where the radicals R 1 , R 3 and R 4 have the same meanings as in the formula I, in the presence of a C 1 -C 6 -alkyl alcohol.

  制备通式（I）中的1,1,4,4-四烷氧基丁-2-烯衍生物的过程，其中基团R1和R2各自独立地为氢、C1-C6烷基、C6-C12芳基（例如苯基）或C5-C12环烷基，或者基团R1和R2与它们所结合的双键共同形成C6-C12芳基基团（例如苯基），该苯基基团被一个或多个C1-C6烷基、卤素原子或烷氧基取代，或者是单不饱和或多不饱和的C5-C12环烷基基团，R3和R4各自独立地为氢、甲基、三氟甲基或腈基。该过程包括在C1-C6烷基醇的存在下，电化学氧化通式（II）中的1,4-二烷氧基-1,3-丁二烯，其中基团R1、R3和R4的含义与通式（I）中的相同。