5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane | 714964-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
• 英文别名: 2-[3-(5-Tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptan-1-yl)phenyl]prop-2-enenitrile；2-[3-(5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptan-1-yl)phenyl]prop-2-enenitrile
• CAS: 714964-21-3
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: MKSBXPSECKJDJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 对二甲苯 为溶剂， 反应 8.0h， 以60%的产率得到3-(1-cyanoethenyl)benzoic acid 2,2,4,4-tetramethyl-3-oxopentyl ester
  参考文献：
  名称：

  Intramolecular charge-transfer-induced chemiluminescent decomposition of 1,2-dioxetanes bearing a phenylmethanide anion

  摘要：

  Dioxetanes (1) bearing a phenyl moiety substituted with a methylene or methine having an electron-withdrawing group(s) (-CH2-Ew or -CH(X)-Ew) and dioxetane (2) bearing a 3-(1-cyanoethenyl)phenyl group were synthesized. Treatment of dioxetanes (1) with tetrabutylammonium fluoride (TBAF) caused their decomposition with accompanying emission of light with maximum wavelength at 530-758 nm. The Michael addition of a bis(methoxycarbonyl)methanide anion to dioxetane (2) produced initially ail unstable dioxetane bearing a phenylmethanide anion, decomposition of which gave light with maximum wavelength at 710-740 nm. Intramolecular cyclopropanation without decomposition of the dioxetane ring took place concurrently for the Michael reaction-induced decomposition of 2 with the bis(methoxycarbonyl)chloromethanide anion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.081
• 作为产物：
  描述：

  4-tert-butyl-5-[3-(1-cyanoethenyl)phenyl]-3,3-dimethyl-2,3-dihydrofuran 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
  参考文献：
  名称：

  通过丙二酸根阴离子的迈克尔加成诱导带有3-（1-氰基乙烯基）苯基部分的二氧杂环丁烷的化学发光分解

  摘要：

  合成具有3-（1-氰基乙烯基）苯基（1）的热稳定的二氧杂环丁烷。发生了将丙二酸根阴离子（3a，b）迈克尔加成到被3-（1-氰基乙烯基）苯基部分取代的二氧杂环丁烷（1）的过程，从而得到了带有苄基阴离子的中间体二氧杂环丁烷，该中间体迅速分解并伴随着深红色的散发。光。当氯丙二酸根（3c）的阴离子用作碱时，3c的分子内环丙烷化与迈克尔加成反应引起的化学发光分解同时发生。

  DOI：

  10.1016/j.tetlet.2004.03.086

文献信息

• Chemiluminescent decomposition of a dioxetane bearing a 3-(1-cyanoethenyl)phenyl moiety induced by Michael addition of an anion of malonate
  作者：Masakatsu Matsumoto、Toshiyuki Mizuno、Nobuko Watanabe

  DOI：10.1016/j.tetlet.2004.03.086

  日期：2004.5

  dioxetane bearing a 3-(1-cyanoethenyl)phenyl group (1) was synthesized. Michael addition of an anion of malonate (3a,b) to a dioxetane (1) substituted with a 3-(1-cyanoethenyl)phenyl moiety took place to give an intermediary dioxetane bearing a benzylic anion, which decomposes rapidly with accompanying emission of crimson light. When an anion of chloromalonate (3c) was used as a base, intramolecular cyclopropanation

  合成具有3-（1-氰基乙烯基）苯基（1）的热稳定的二氧杂环丁烷。发生了将丙二酸根阴离子（3a，b）迈克尔加成到被3-（1-氰基乙烯基）苯基部分取代的二氧杂环丁烷（1）的过程，从而得到了带有苄基阴离子的中间体二氧杂环丁烷，该中间体迅速分解并伴随着深红色的散发。光。当氯丙二酸根（3c）的阴离子用作碱时，3c的分子内环丙烷化与迈克尔加成反应引起的化学发光分解同时发生。
• Intramolecular charge-transfer-induced chemiluminescent decomposition of 1,2-dioxetanes bearing a phenylmethanide anion
  作者：Nobuko Watanabe、Toshiyuki Mizuno、Masakatsu Matsumoto

  DOI：10.1016/j.tet.2005.07.081

  日期：2005.10

  Dioxetanes (1) bearing a phenyl moiety substituted with a methylene or methine having an electron-withdrawing group(s) (-CH2-Ew or -CH(X)-Ew) and dioxetane (2) bearing a 3-(1-cyanoethenyl)phenyl group were synthesized. Treatment of dioxetanes (1) with tetrabutylammonium fluoride (TBAF) caused their decomposition with accompanying emission of light with maximum wavelength at 530-758 nm. The Michael addition of a bis(methoxycarbonyl)methanide anion to dioxetane (2) produced initially ail unstable dioxetane bearing a phenylmethanide anion, decomposition of which gave light with maximum wavelength at 710-740 nm. Intramolecular cyclopropanation without decomposition of the dioxetane ring took place concurrently for the Michael reaction-induced decomposition of 2 with the bis(methoxycarbonyl)chloromethanide anion. (c) 2005 Elsevier Ltd. All rights reserved.