(Z,Z,Z)-1,19-Dioxo-2,7,8,12,13,18-hexamethyl-3,17-diethyl-1,19,22,24-tetrahydro-21H-bilin | 33255-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (Z,Z,Z)-1,19-Dioxo-2,7,8,12,13,18-hexamethyl-3,17-diethyl-1,19,22,24-tetrahydro-21H-bilin
• 英文别名: etiobiliverdin IVγ；3,8,12,17-Tetraethyl-1,19,21,24-tetrahydro-2,7,13,18-tetramethyl-1,19-dioxo-22H-bilin；etiobiliverdin XIII_α；(Z,Z,Z)-Aetiobiliverdin-IV-γ；Aetiobiliverdin-IV-γ；Etiobiliverdin-IV-γ
• CAS: 33255-44-6
• 化学式: C₃₁H₃₈N₄O₂
• 分子量: 498.668
• InChiKey: CJAPEMWQYNKUMD-CORWYUFQSA-N

物化性质

• 熔点：
  262-265 °C
• 沸点：
  736.4±60.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  86.35
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z,Z,Z)-1,19-Dioxo-2,7,8,12,13,18-hexamethyl-3,17-diethyl-1,19,22,24-tetrahydro-21H-bilin 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 (Z,Z,Z)-1,19-Dioxo-3,8,12,17-tetraethyl-2,7,13,18-tetramethyl-21,24-methylen-1,10,19,22,23,24-hexahydro-21 H-bilin
  参考文献：
  名称：

  Beiträgezur chemie der pyrrolpigmente-XXXVII：苯丁酸酯：N 21 -N 24-亚甲基-胆碱素-IV- γ和N 21 - N 24-亚甲基-胆碱素-IV- γ

  摘要：

  DOI：

  10.1016/s0040-4020(01)97694-x
• 作为产物：
  描述：

  8-des-ethylkryptopyrromethenone 在 sodium tetrahydroborate 、 三氯化铝 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z,Z,Z)-1,19-Dioxo-2,7,8,12,13,18-hexamethyl-3,17-diethyl-1,19,22,24-tetrahydro-21H-bilin
  参考文献：
  名称：

  Efficient Routes to ω-Chloroalkyl Bilirubins and C12-N22 Bridged Biliverdins

  摘要：

  omega -Chloroalkyl biliverdins, prepared in three steps from 8-unsubstituted dipyrrinones in 70-80% overall yields, were reduced by sodium borohydride to provide the corresponding omega -chloroalkyl bilirubins in high yields. Upon treatment of the omega -chloroalkyl biliverdins with sodium hydroxide in ethanol, C12-N22 bridged biliverdins were obtained in high yields.

  DOI：

  10.1007/s007060170084

文献信息

• Converting 9-methyldipyrrinones to 9-H and 9-CHO dipyrrinones
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1016/j.tet.2007.06.009

  日期：2007.9

  afford yellow 9-H dipyrrinones, and 9-CHO dipyrrinones as their violet to orange colored adducts with the carbon acid used for the scission: thiobarbituric acid (TBA), N,N'-diethylthiobarbituric acid, barbituric acid, N,N'-dimethylbarbituric acid and Meldrum's acid. The adducts, usually only of passing interest, are formally Knovenagel condensation products of a 9-CHO dipyrrinone with TBA and other

  黄色的 9-甲基二吡啉酮可以很容易地以高产率转化为对称的线性四吡咯、蓝色胆绿素，它们在室温下顺利地分裂成两半，得到黄色的 9-H 二吡啉酮和 9-CHO 二吡喃酮作为它们的紫色到橙色加合物与用于断裂的碳酸：硫代巴比妥酸 (TBA)、N,N'-二乙基硫代巴比妥酸、巴比妥酸、N,N'-二甲基巴比妥酸和 Meldrum 酸。加合物，通常只是暂时的兴趣，形式上是 9-CHO 双吡喃酮与 TBA 和本工作的其他碳酸的 Knovenagel 缩合产物，并且此类加合物的反向 Knovenagel 反应导致 9-CHO 双吡喃酮。在一组改进的反应条件下，该序列因此有效地将 9-CH(3) 双吡啉酮转化为 9-H 和 9-CHO 双吡喃酮。
• Helical Chirality Induction in Zinc Bilindiones by Amino Acid Esters and Amines
  作者：Tadashi Mizutani、Shigeyuki Yagi、Atsushi Honmaru、Shinji Murakami、Masaru Furusyo、Toru Takagishi、Hisanobu Ogoshi

  DOI：10.1021/jo980819j

  日期：1998.11.1

  Complexation of alpha-amino acid esters, beta-amino ethers, and amines with a series of zinc 1,19-bilindione derivatives was studied, particularly focusing on the helical chirality induction in the bilindione framework triggered by the binding of chiral guests. Comparative studies of binding and helical chirality induction indicated that binding and chiral induction were markedly affected by polar substituents present in both zinc bilindiones and guests. 2-Hydroxyethyl groups at the 2,18-positions of zinc bilindione largely assisted the binding of amines and amino acid esters but not the chiral induction. 19O-Alkylation of the zinc bilindiones had inhibitory effects on the binding but enhanced efficiency of helical chirality induction. The enantiomeric excess of 19O-alkyl zinc bilindione complexed with L-Trp-OMe in CD2Cl2 was 73% at 223 K. A COOR group and an aromatic group in the guest promoted helical chirality induction of 19O-alkylated zinc bilindiones. The patterns of H-1 NMR complexation-induced shifts of zinc bilindiones and guests and a molecular modeling study of the complexes showed that electrostatic repulsion between the COOR group of amino acid esters and the lactam ring of zinc bilindiones, and stacking of the side chain groups of amino acid esters on the C ring of zinc bilindione made a significant contribution to efficient helical chirality induction.
• Reaktivität von Pyrrolpigmenten, 15 Mitt.: Über die Oxidation von Bilirubinen und Biliverdinen
  作者：C. Acero、J. M. Ribó、R. Solé、F. R. Trull

  DOI：10.1007/bf00814136

  日期：1993.4

  Characteristic oxidation reactions of bilin-1,19-diones (biliverdins) and biladien-ac-1,19-diones (bilirubins) were reinvestigated. These include bromine and iodine oxidation of biliverdin IXalpha bilirubin IXalpha and their Zn(II) complexes, the reaction described by Siedel (1941) of mesobilirubin XIIIalpha dimethyl ester with nitric acid (Gmelin reaction) and Smith's oxidation (1977) of etiobiliverdin IVgamma using Tl triacetate and Pb tetra-acetate. For some of these reaction products new structures were assigned on the basis of their spectrometric data. These structures agreed with the expected reactivity pattern of biliverdins and bilirubins.
• 1,2-bis-Dipyrrinon-9-yl-ethene ? a novelb-homo-verdian chromophore: the reaction of 9-methyl-10H-dipyrrin-1-ones with bromine
  作者：Q. -Q. Chen、J. -S. Ma、C. -Q. Wang、Y. -Y. Liu、F. Yan、L. -J. Cheng、S. Jin、H. Falk

  DOI：10.1007/bf00811018

  日期：——

  Upon treatment of 9-methyl-10H-dipyrrin-1-ones with bromine in dichloromethane, red bile pigment derivatives were obtained in moderate yields. They were structurally assigned as 1,2-bis-dipyrrinon-9-yl-ethenes, which are examples of the hitherto unknown h-homo-verdins. In addition, the corresponding meso-biliverdins-XIII alpha could be isolated from the reaction mixture. The mechanistic aspects of the reaction are discussed.
• Falk, Heinz; Thirring, Klaus, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1980, vol. 35, # 3, p. 376 - 380
  作者：Falk, Heinz、Thirring, Klaus

  DOI：——

  日期：——