diethyl 2-(2-adamantylidene)butanedioate | 70477-64-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 2-(2-adamantylidene)butanedioate
• 英文别名: diethyl adamant-2-ylidenesuccinate；adamantylidene diethyl succinate；diethyl adamantylidene succinate；diethyl adamantylidenesuccinate；Diethyl adamantylidensuccinate
• CAS: 70477-64-4
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: CERSLUYUTAKPSN-ICFOKQHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-adamantylidene)butanedioate 在 lithium diisopropyl amide 作用下， 生成 ABERCHROME 670
  参考文献：
  名称：

  Yokoyama, Yasushi; Iwai, Takeshi; Kera, Naohiko, Chemistry Letters, 1990, # 2, p. 263 - 264

  摘要：

  DOI：
• 作为产物：
  描述：

  金刚烷酮 、 丁二酸二乙酯 在 potassium tert-butylate 、 盐酸 、 乙醇 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以54%的产率得到diethyl 2-(2-adamantylidene)butanedioate
  参考文献：
  名称：

  Improved Synthesis of Indolyl Fulgides

  摘要：

  DOI：

  10.1021/jo005722n

文献信息

• Effects of Steric Bulkiness of Substituents on Quantum Yields of Photochromic Reactions of Furylfulgides
  作者：Yasushi Yokoyama、Tetsushi Inoue、Masato Yokoyama、Takakazu Goto、Takeshi Iwai、Naohiko Kera、Isamu Hitomi、Yukio Kurita

  DOI：10.1246/bcsj.67.3297

  日期：1994.12

  Furylfulgides with different sizes of alkyl substituents were synthesized and their photochromic properties were examined. While the quantum yield of coloring reaction increased and the quantum yield of the E-to-Z isomerization decreased as the steric bulkiness of the alkyl substitutent on the 2,5-dimethyl-3-furylmethylidene moiety increased, the bleaching quantum yield increased as the isopropylidene

  合成了具有不同大小烷基取代基的呋喃磺酰氯并检测了它们的光致变色性能。虽然随着 2,5-二甲基-3-呋喃亚甲基部分上烷基取代基的空间体积增加，着色反应的量子产率增加，E-to-Z 异构化的量子产率降低，但漂白量子产率随着异亚丙基被金刚烷基取代。两种效应独立起作用，并且在一个分子中具有异丙基的呋喃亚甲基部分和金刚烷亚基的呋喃酰氟酸在甲苯中显示出 0.51 (366 nm) 的着色量子产率和 0.26 (492 nm) 的漂白量子产率。
• Steric Effects of Substituents on the Photochromism of Indolylfulgides
  作者：Soichi Uchida、Shintaro Yamada、Yasushi Yokoyama、Yukio Kurita

  DOI：10.1246/bcsj.68.1677

  日期：1995.6

  with a bulky 1-alkyl-1-indolylmethylidene and/or a bulky alkylidene substituent were synthesized and their photochromic as well as absorption spectroscopic properties were compared with those of the known prototype indolylfulgide, 3-[1-(1,2-dimethyl-3-indolyl)ethylidene]-4-isopropylidenedihydro-2,5-furandione. An increase in steric bulkiness of the alkyl group (R1) on the indolylmethylidene group increased

  合成了具有庞大的 1-烷基-1-吲哚基亚甲基和/或庞大的亚烷基取代基的光致变色富酸酐，并将它们的光致变色和吸收光谱性质与已知原型吲哚基富酸酐、3-[1-(1,2-二甲基-3-吲哚基)亚乙基]-4-异亚丙基二氢-2,5-呋喃二酮。吲哚亚甲基上烷基 (R1) 的空间体积增加增加了着色量子产率 (ΦEC = 0.046 (R1 = 甲基) 至 0.31 (R1 = 异丙基))，而其他亚烷基的空间体积增加组 (R2) 增加了漂白量子产率 (ΦCE = 0.051 (R2 = 异丙叉) 到 0.42 (R2 = 2-金刚烷基))。然而，当 R1 和 R2 都很大时，着色量子产率并不大，尽管漂白量子产率仍然很大。
• Synthesis, structure, and spectral and photochemical properties of fulgides of the indole series with an adamantylidene fragment
  作者：S. M. Aldoshin、A. N. Utenyshev、A. V. Metelitsa、M. I. Knyazhanskii、O. T. Lyashik、E. A. Medyantseva、V. I. Minkin

  DOI：10.1007/bf01430736

  日期：1996.9

  of the indole series with adamantylidene fragments were synthesized: 3-(adamant-2-ylidene)-2-[1′-(3′-indolylethylidene)]succinic anhydride (I) and 3-(adamant-2-ylidene)-2-(3′-indolylmethylene)]succinic anhydride (2). By means of electronic absorption and1H NMR spectroscopy and X-ray diffraction analysis, fulgides1 and2 were shown to haveZ- andE-configurations, respectively. The photochemical properties

  合成了具有金刚烷基片段的吲哚系列的新硫化物：3-(adamant-2-ylidene)-2-[1'-(3'-indoylethylidene)]琥珀酸酐 (I) 和 3-(adamant-2-ylidene) -2-(3'-吲哚亚甲基)]琥珀酸酐 (2)。通过电子吸收和 1 H NMR 光谱和 X 射线衍射分析，显示出富酸酐 1 和 2 分别具有 Z 和 E 构型。研究了1和2的光化学性质。结果表明，随着这些化合物的 Z-E 光异构化，它们在溶液中发生环化反应以产生有色光产物。讨论了影响其光化学性质的 fulgide1 的特定结构特征。大金刚烷基的引入降低了化合物 1 向环状异构体 C 的转化程度。
• Helioghromic Fulgides of Indole Species
  作者：Oieg Y. Fedorovskiy、Yriy M. Chunaev、Lidiya N. Kurkovskaya、Nina M. Prghiyalgovskaya、Nikolay O. Pirogov

  DOI：10.1080/10587259408037789

  日期：1994.5

  For three fulgides photochromic behaviour was described. Also synthesis of this fulgides was described.
• Photochromism and Kinetics of Heliochromic Benzothienylfulgides
  作者：Yasushi Yokoyama、Hiroshi Nakata、Koichi Sugama、Yayoi Yokoyama

  DOI：10.1080/10587250008023845

  日期：2000.6.1

  Four heliochromic benzothienylfulgides were synthesized and their spectral properties, photochromism, and the decoloration kinetics were examined. Photocyclization of E-form occurred on the benzothiophene ring but not on the phenyl ring for 4 and 5, Introduction of an isopropyl group (3) or a phenyl group (4, 5) on the benzothienylmethylidene group retarded the decoloration rate of O-forms. Introduction of a phenyl group (4, 5) also resulted in 40-nm red-shift of absorption and three-fold increase in molar absorption coefficients of O-forms in the Visible region.