methyl 4-formyl-9-isopropyl-1,6-dimethylheptalene-5-carboxylate | 188635-43-0

• 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-formyl-9-isopropyl-1,6-dimethylheptalene-5-carboxylate
• 英文别名: Methyl 2-formyl-5,10-dimethyl-7-propan-2-ylheptalene-1-carboxylate；methyl 2-formyl-5,10-dimethyl-7-propan-2-ylheptalene-1-carboxylate
• CAS: 188635-43-0
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: CWHIXAXYFUAMCK-UHFFFAOYSA-N

物化性质

• 沸点：
  493.9±28.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-formyl-9-isopropyl-1,6-dimethylheptalene-5-carboxylate 在 正丁基锂 、 swern reagent 、 二异丁基氢化铝 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.17h， 生成 1,2-Diethynyl-5,10-dimethyl-7-propan-2-ylheptalene
  参考文献：
  名称：

  Abou-Hadeed, Khaled, Chimia, 2000, vol. 54, # 12, p. 763 - 765

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 9-isopropyl-1,6-dimethylheptalene-4,5-dicarboxylate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 以78%的产率得到methyl 4-formyl-9-isopropyl-1,6-dimethylheptalene-5-carboxylate
  参考文献：
  名称：

  带有扩展π系统的新庚烯的合成与表征

  摘要：

  型的甲基heptalenecarboxylates阿和乙与π（1）和π（2）的1,4-二关系（取代基方案1）中synthetized开始用二甲基-1- methylheptalene -4,5-二羧酸5B和6B从7-异丙衍生-1,4-二甲基az（=愈创木z）和1,4,6,8-四甲基az与乙酰二羧酸二甲酯发生热反应。流程3显示了引入π（1）和π（2）取代基的另一种通用方法，由此获得的A和B型甲基庚烯-5-羧酸酯中列出表1的2-arylethenyl和4- arylbuta -1,3-二烯-1-基团的CC键π（1）和π（2）在所有情况下（É）构型并在B型以及A型庚二烯中在CC键（X射线和1 H-NOE证据）处显示了反式构象（参见图5-12）。

  DOI：

  10.1002/hlca.201300137

文献信息

• New Heptalenes Substituted with Extended ?-Systems
  作者：Sarah El Houar、Hans-J�rgen Hansen

  DOI：10.1002/hlca.19970800123

  日期：1997.2.10

  4-conjugative switch (CS) system show typical heptalene UV/VIS spectra with a bathochromically shifted heptalene band III and comparably weak heptalene bands II and I which appear only as shoulders (Figs. 4 and 5). In contrast, the DBS isomers (all-E)-17b and (all-E)-22b, equivalent to the on-state of a 1,4-CS system, exhibit extremely intense heptalene bands I and, possibly, II which appear as a broad

  从容易获得的二甲基9-异丙基-1、6-二甲基庚烯-4、5-二羧酸酯（2b）开始，描述了π-取代的庚烯羧酸酯或-二羧酸酯的合成。的治疗2B与叔丁醇钾和C 2氯6在-78℃，因而在ME-C（1）化学选择性引入氯取代基的（参见图5b中方案1）。通过碘化物6b（方案2）形成相应的三苯基phosph盐7b使得在两相体系CH 2 Cl 2中与肉桂醛发生维蒂希反应。/ 2N NaOH。将2b的4、5-二氟甲磺酸酯转化为相应的拟酯10b，可以用DIBAH选择性还原C（4）处的羰基官能团，得到相应的4-甲醛11b（方案3）。11b与（苄基）三苯基溴化的Wittig反应导致在C（4）处引入4-苯基丁1-1、3-二烯基取代基。两者的结合维蒂希导致了1，4-双（4-苯-1- -1,3-二烯基）的合成反应取代的庚搭烯-5-羧酸甲酯（全-E） - 17B（方案5）。以类似的方式，通过应用Horner-Wadswort
• 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.
• Synthesis and Characterization of New Heptalenes with Extended<i>π</i>-Systems Attached to Them
  作者：Sarah Maillefer-El Houar、Peter Uebelhart、Anthony Linden、Hans-Jürgen Hansen

  DOI：10.1002/hlca.201300137

  日期：2013.8

  displayed in Scheme 3, and the thus obtained methyl heptalene‐5‐carboxylates of type A and B are listed in Table 1. The CC bonds of the 2‐arylethenyl and 4‐arylbuta‐1,3‐dien‐1‐yl groups of π(1) and π(2) were in all cases (E)‐configured and showed s‐trans conformation at the CC bonds (X‐ray and 1H‐NOE evidence) in the B‐type as well as in the A‐type heptalenes (cf. Figs. 5–12).

  型的甲基heptalenecarboxylates阿和乙与π（1）和π（2）的1,4-二关系（取代基方案1）中synthetized开始用二甲基-1- methylheptalene -4,5-二羧酸5B和6B从7-异丙衍生-1,4-二甲基az（=愈创木z）和1,4,6,8-四甲基az与乙酰二羧酸二甲酯发生热反应。流程3显示了引入π（1）和π（2）取代基的另一种通用方法，由此获得的A和B型甲基庚烯-5-羧酸酯中列出表1的2-arylethenyl和4- arylbuta -1,3-二烯-1-基团的CC键π（1）和π（2）在所有情况下（É）构型并在B型以及A型庚二烯中在CC键（X射线和1 H-NOE证据）处显示了反式构象（参见图5-12）。
• Abou-Hadeed, Khaled, Chimia, 2000, vol. 54, # 12, p. 763 - 765
  作者：Abou-Hadeed, Khaled

  DOI：——

  日期：——