1,3,3-tributoxy-2-cyanopropene | 87466-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,3-tributoxy-2-cyanopropene
• 英文别名: 3-Butoxy-2-(dibutoxymethyl)prop-2-enenitrile
• CAS: 87466-80-6
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: WCJTULPFKRGBNH-UHFFFAOYSA-N

物化性质

• 沸点：
  376.3±42.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3,3-tributoxy-2-cyanopropene 在 水 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 生成 3-butoxy-2-cyanoacrolein
  参考文献：
  名称：

  一种新颖的串联跨醚化反应-分子间杂Diels-Alder反应用于稠合杂环的构建

  摘要：

  当在热条件下与δ，ε-不饱和醇反应时，被附加的吸电子取代基激活的β-烷氧基取代的α，β-不饱和羰基化合物会发生容易的串联反醚化/分子间杂Diels-Alder反应。这些反应是立体选择性的，以高收率产生了相应的官能化氢吡喃吡喃衍生物。

  DOI：

  10.1016/s0040-4039(99)02003-1

文献信息

• A Study on the Relationship between the Twisted π-Conjugate System of 1,5-Diaryl-1,5-diazapenta-1,3-dienes and Their Photophysical Properties
  作者：Akio Kamimura、Hideki Matsu、Hiroyuki Suzukawa、Eisuke Sato、Michinori Sumimoto、Hidemitsu Uno

  DOI：10.1246/cl.2012.984

  日期：2012.9.5

  One-pot treatment of commercially available 1,3,3-tributoxy-2-cyanopropene with 2 equivalents of primary aromatic amines readily afforded 1,5-diaryl-1,5-diaza-3-cyanopenta-1,3-dienes. UV properties varied as steric size of the ortho-substituent in the N-aryl units increased. X-ray crystallographic analyses indicated preferable conformation of these compounds, and the twist angles between 1,5-diazapentadiene and aromatic units were measured. The relationship between the twisted angles and UV absorptions was rationalized by MO calculation, and the UV peak wavelengths are useful for the estimation of the twisted angles. A novel tetracoordinate diaryl-1,5-diazapentadiene was prepared. UV spectrum for its lithium complex in CHCl3 supported that the complex had a twisted conformation of the aryl units because the two etharial oxygen atoms coordinated to lithium cation.

  将市售的 1,3,3-三丁氧基-2-氰基丙烯与 2 个等量的芳香族伯胺进行一锅处理，很容易得到 1,5-二芳基-1,5-二氮杂-3-氰基戊-1,3-二烯。随着 N-芳基单元中正位取代基立体尺寸的增加，紫外特性也随之变化。X 射线晶体学分析表明了这些化合物的优选构象，并测量了 1,5-二氮杂戊二烯与芳香单元之间的扭角。扭角与紫外吸收之间的关系通过 MO 计算得到了合理解释，紫外峰值波长有助于估算扭角。制备了一种新型四配位二芳基-1,5-二氮杂戊二烯。其锂络合物在 CHCl3 中的紫外光谱证明，由于两个乙氧基与锂阳离子配位，该络合物的芳基单元具有扭曲构象。
• Chirality transfer in the ene-reactions of 3-{2-(2S)-[2-(substituted)vinyl]pyrrolidin-1-yl}-2-(substituted)acrolein derivatives
  作者：Michihiko Noguchi、Ryo Matsushita、Shinji Takamura、Takehiko Uchida、Akikazu Kakehi、Motoo Shiro、Hidetoshi Yamamoto

  DOI：10.1016/s0040-4039(00)01536-7

  日期：2000.10

  Ene-reactions of 3-2-(2S)-[2-(substituted)vinyl]pyrrolidin-1-yl}-2-(substituted)acrolein derivatives 5, 8, 13, and 16 have been described. Carbonyl-ene reaction of 5 and 16 and imine-ene reaction of 8 proceeded in a highly selective manner to lead to azepine derivatives 6 and 17, and 9, respectively. The chirality of the starting acroleins was transferred almost perfectly to the azepine-ring through

  3-烯反应2-（2-小号） - [2-（取代的）乙烯基]吡咯烷-1-基} -2-（取代的）丙烯醛衍生物5，8，13，和16已被描述。的羰基-烯反应5和16的和亚胺-烯反应8以高度选择性的方式进行到导致吖庚因衍生物6和17，和9分别。起始丙烯醛的手性通过烯反应几乎完美地转移到a庚环上。
• Stereoselective Azepine-Ring Formation Through Ene Reactions of 3-(Alk-2-enyl)amino-2-cyanoacrolein Derivatives
  作者：Michihiko Noguchi、Hisashi Yamada、Shinji Takamura、Takehiko Uchida、Mitsuko Hironaka、Akikazu Kakehi、Hidetoshi Yamamoto

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1489::aid-ejoc1489>3.0.co;2-z

  日期：2000.4

  The reaction of 3-[N-(alk-2-enyl)benzylamino]-2-cyanoacroleins 9 with primary amines 12 and 13 gave 4,5-dihydro-1H-azepines 14 and 15 stereoselectively, through an intramolecular ene reaction of the imine derivatives of 9. Similarly, carbonyl-ene reaction of acrolein derivatives 9, and olefin-ene reaction of their conjugated diene compounds 22, and 24-27 are also discussed. These ene reactions established

  3-[N-(alk-2-enyl)benzylamino]-2-cyanoacroleins 9 与伯胺 12 和 13 的反应得到 4,5-dihydro-1H-azepines 14 和 15 立体选择性，通过分子内烯反应9 的亚胺衍生物。类似地，还讨论了丙烯醛衍生物 9 的羰基-烯反应，以及它们的共轭二烯化合物 22 和 24-27 的烯烃-烯反应。这些烯反应为单环氮杂环的形成建立了一种有效的合成方法。
• Process for preparing 4-amino-5-dialkoxy-methylpyrimidine derivatives
  申请人：Ube Industries, Ltd.

  公开号：US04492792A1

  公开（公告）日：1985-01-08

  A process for preparing a 4-amino-5-dialkoxymethylpyrimidine derivative of the formula: ##STR1## which comprises reacting a propanenitrile derivative represented by the formula (I) or the novel compound represented by formula (II): ##STR2## with an amidine of the formula: ##STR3## wherein R.sup.1 to R.sup.6 are as defined in the specification. Also disclosed is a process for making the novel compounds of formula (II).

  一种制备4-氨基-5-二烷氧甲基嘧啶衍生物的方法，该衍生物的化学式为：##STR1## 该方法包括将由化学式（I）表示的丙腈衍生物或由化学式（II）表示的新化合物：##STR2## 与化学式为：##STR3## 的酰胺反应，其中R.sup.1至R.sup.6如说明书中所定义。还公开了制备化学式（II）的新化合物的方法。
• Takamura; Yamada; Michinaka, Journal of Chemical Research - Part S, 2000, # 9, p. 426 - 428
  作者：Takamura、Yamada、Michinaka、Yamamoto、Kakehi、Noguchi

  DOI：——

  日期：——