methyl 4-cyano-9-isopropyl-1,6-dimethylheptalene-5-carboxylate | 394212-99-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 4-cyano-9-isopropyl-1,6-dimethylheptalene-5-carboxylate
• 英文别名: Methyl 2-cyano-5,10-dimethyl-7-propan-2-ylheptalene-1-carboxylate；methyl 2-cyano-5,10-dimethyl-7-propan-2-ylheptalene-1-carboxylate
• CAS: 394212-99-8
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: LLCSAGVLSSEEBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(二甲氧基甲基)吡咯烷 、 methyl 4-cyano-9-isopropyl-1,6-dimethylheptalene-5-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以97%的产率得到2-Cyano-7-isopropyl-10-methyl-5-((E)-2-pyrrolidin-1-yl-vinyl)-heptalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  供体-受体-取代庚烯的光谱研究

  摘要：

  It is shown that the heptalene-4.5-dicarboxylates 5 react with their Me group at C(1) with N,N-dimethylformamide dimethyl acetal or other acetals of this type in N,N-dimethylformamide (DMF) to give the corresponding 1-[(E)-2-(N,N-dialkylamino)ethenyl]-substituted heptalene-4,5-dicarboxylates 8a-8e as well as 8k and 8i in good yields (Table 1). In a similar manner, the 1-[(E)-2-pyrrolidinoethenyl]-substituted heptalene-5-carboxylates 8f-h were synthesized from the corresponding heptalene-carboxylates 10-12, carrying a CHO, CN. or (E)-2-(methoxycarbonyl)ethenyl group at C(4) (Table 1). All new heptalenes with the pi -donor and pi -acceptor groups at C(1) and C(4), respectively, exhibit a strongly enhanced heptalene band I in the spectral region of 450-500 nm in MeCN (Table 7 and Figs. 4-7), whereby the specific position is dependent on the pi -donor quality of the N,N-dialkylamino substituent at C(2') and the pi -acceptor property of the group at C(4). The position of heptalene band I is also strongly solvent-dependent as is demonstrated in the case of heptalene 8i (Table 9). A good linear correlation with the CT band of 1-(diethylamino)-4-nitrobenzene or (E)-4-(dimethylamino)-beta -nitrostyrene (Figs. 11 and 12) characterizes the heptalene band I also as an electronic CT transition. Irradiation into this band of 8i leads, as observed in other cases (cf. [I I), to a double-bond shift in the heptalene moiety (--> 8'i: Figs. 8-10). On warming in solution, 8'i is converted quantitatively to 8i.

  DOI：

  10.1002/1522-2675(20010919)84:9<2670::aid-hlca2670>3.0.co;2-p
• 作为产物：
  描述：

  methyl 4-formyl-9-isopropyl-1,6-dimethylheptalene-5-carboxylate 在 吡啶 、 盐酸羟胺 、 copper(II) sulfate 、 N,N'-二环己基碳二亚胺 、 三甲胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 methyl 4-cyano-9-isopropyl-1,6-dimethylheptalene-5-carboxylate
  参考文献：
  名称：

  供体-受体-取代庚烯的光谱研究

  摘要：

  It is shown that the heptalene-4.5-dicarboxylates 5 react with their Me group at C(1) with N,N-dimethylformamide dimethyl acetal or other acetals of this type in N,N-dimethylformamide (DMF) to give the corresponding 1-[(E)-2-(N,N-dialkylamino)ethenyl]-substituted heptalene-4,5-dicarboxylates 8a-8e as well as 8k and 8i in good yields (Table 1). In a similar manner, the 1-[(E)-2-pyrrolidinoethenyl]-substituted heptalene-5-carboxylates 8f-h were synthesized from the corresponding heptalene-carboxylates 10-12, carrying a CHO, CN. or (E)-2-(methoxycarbonyl)ethenyl group at C(4) (Table 1). All new heptalenes with the pi -donor and pi -acceptor groups at C(1) and C(4), respectively, exhibit a strongly enhanced heptalene band I in the spectral region of 450-500 nm in MeCN (Table 7 and Figs. 4-7), whereby the specific position is dependent on the pi -donor quality of the N,N-dialkylamino substituent at C(2') and the pi -acceptor property of the group at C(4). The position of heptalene band I is also strongly solvent-dependent as is demonstrated in the case of heptalene 8i (Table 9). A good linear correlation with the CT band of 1-(diethylamino)-4-nitrobenzene or (E)-4-(dimethylamino)-beta -nitrostyrene (Figs. 11 and 12) characterizes the heptalene band I also as an electronic CT transition. Irradiation into this band of 8i leads, as observed in other cases (cf. [I I), to a double-bond shift in the heptalene moiety (--> 8'i: Figs. 8-10). On warming in solution, 8'i is converted quantitatively to 8i.

  DOI：

  10.1002/1522-2675(20010919)84:9<2670::aid-hlca2670>3.0.co;2-p

文献信息

• A Spectroscopic Investigation of Donor-Acceptor-Substituted Heptalenes
  作者：Philipp Ott、Hans-Jürgen Hansen

  DOI：10.1002/1522-2675(20010919)84:9<2670::aid-hlca2670>3.0.co;2-p

  日期：2001.9.19

  It is shown that the heptalene-4.5-dicarboxylates 5 react with their Me group at C(1) with N,N-dimethylformamide dimethyl acetal or other acetals of this type in N,N-dimethylformamide (DMF) to give the corresponding 1-[(E)-2-(N,N-dialkylamino)ethenyl]-substituted heptalene-4,5-dicarboxylates 8a-8e as well as 8k and 8i in good yields (Table 1). In a similar manner, the 1-[(E)-2-pyrrolidinoethenyl]-substituted heptalene-5-carboxylates 8f-h were synthesized from the corresponding heptalene-carboxylates 10-12, carrying a CHO, CN. or (E)-2-(methoxycarbonyl)ethenyl group at C(4) (Table 1). All new heptalenes with the pi -donor and pi -acceptor groups at C(1) and C(4), respectively, exhibit a strongly enhanced heptalene band I in the spectral region of 450-500 nm in MeCN (Table 7 and Figs. 4-7), whereby the specific position is dependent on the pi -donor quality of the N,N-dialkylamino substituent at C(2') and the pi -acceptor property of the group at C(4). The position of heptalene band I is also strongly solvent-dependent as is demonstrated in the case of heptalene 8i (Table 9). A good linear correlation with the CT band of 1-(diethylamino)-4-nitrobenzene or (E)-4-(dimethylamino)-beta -nitrostyrene (Figs. 11 and 12) characterizes the heptalene band I also as an electronic CT transition. Irradiation into this band of 8i leads, as observed in other cases (cf. [I I), to a double-bond shift in the heptalene moiety (--> 8'i: Figs. 8-10). On warming in solution, 8'i is converted quantitatively to 8i.