Pheo-d | 26396-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: Pheo-d
• 英文别名: pheophytin d；pheophytin-d；3-formyl-3-devinyl-pheophytin-a；3-Formyl-3-desvinyl-phaeophytin-a
• CAS: 26396-77-0
• 化学式: C₅₄H₇₂N₄O₆
• 分子量: 873.189
• InChiKey: ROXSFRRXMAYAHO-UWZIYXPOSA-N

物化性质

• 沸点：
  1047.9±65.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.13
• 重原子数：
  64.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  144.1
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 Pheo-d
  参考文献：
  名称：

  Manning; Strain, Journal of Biological Chemistry, 1943, vol. 151, p. 1,14

  摘要：

  DOI：

文献信息

• Ene-thiol reaction of <font>C</font>3-vinylated chlorophyll derivatives in the presence of oxygen: synthesis of <font>C</font>3-formyl-chlorins under mild conditions
  作者：Takanori Fukusumi、Natsuki Takei、Yubi Tateno、Takuya Aoki、Ai Ando、Kouhei Kozakai、Hiroko Shima、Tadashi Mizoguchi、Satoshi Ito、Tsukasa Ikeda、Hitoshi Tamiaki、Toru Oba

  DOI：10.1142/s1088424613500983

  日期：2013.12

  Reactions of thiol with the C 3-vinyl group of various chlorophyll (Chl) derivatives were examined. The reactions resemble thiol-olefin co-oxidation, except that the vinyl C = C double bond was cleaved to afford a formyl group without any transition metal catalyst, and that the simple anti-Markovnikov adduct of thiol to olefin was obtained as a minor product. Peripheral substituents of Chl derivatives little affected the reaction, while the central metal atom of the chlorin macrocycle influenced the composition of the products. Oxygen and acid dissolved in the reaction mixture can facilitate the oxidation. Sufficiently mild conditions in this regioselective oxidation at the C 3¹-position are significant in bioorganic chemistry.

  研究了硫醇与各种叶绿素（Chl）衍生物的 C 3-乙烯基的反应。这些反应类似于硫醇与烯烃的共氧化反应，只是乙烯基 C = C 双键在没有任何过渡金属催化剂的情况下被裂解以产生甲酰基，而且硫醇与烯烃的简单反马尔科夫尼科夫加合物作为次要产物被获得。Chl 衍生物的外围取代基对反应的影响很小，而氯素大环的中心金属原子则会影响产物的组成。溶解在反应混合物中的氧气和酸可促进氧化。在这种 C 31 位的区域选择性氧化反应中，足够温和的条件在生物有机化学中具有重要意义。
• Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 3: The Distinctive Impact of Auxochromes at the 7- versus 3-Positions
  作者：Joseph W. Springer、Kaitlyn M. Faries、James R. Diers、Chinnasamy Muthiah、Olga Mass、Hooi Ling Kee、Christine Kirmaier、Jonathan S. Lindsey、David F. Bocian、Dewey Holten

  DOI：10.1111/j.1751-1097.2012.01083.x

  日期：2012.5

  AbstractAssessing the effects of substituents on the spectra of chlorophylls is essential for gaining a deep understanding of photosynthetic processes. Chlorophyll a and b differ solely in the nature of the 7‐substituent (methyl versus formyl), whereas chlorophyll a and d differ solely in the 3‐substituent (vinyl versus formyl), yet have distinct long‐wavelength absorption maxima: 665 (a) 646 (b) and 692 nm (d). Herein, the spectra, singlet excited‐state decay characteristics, and results from DFT calculations are examined for synthetic chlorins and 131‐oxophorbines that contain ethynyl, acetyl, formyl and other groups at the 3‐, 7‐ and/or 13‐positions. Substituent effects on the absorption spectra are well accounted for using Gouterman’s four‐orbital model. Key findings are that (1) the dramatic difference in auxochromic effects of a given substituent at the 7‐ versus3‐ or 13‐positions primarily derives from relative effects on the LUMO+1 and LUMO; (2) formyl at the 7‐ or 8‐position effectively “porphyrinizes” the chlorin and (3) the substituent effect increases in the order of vinyl < ethynyl < acetyl < formyl. Thus, the spectral properties are governed by an intricate interplay of electronic effects of substituents at particular sites on the four frontier MOs of the chlorin macrocycle.
• Effects of molecular structures on reduction properties of formyl groups in chlorophylls and pheophytins prepared from oxygenic photosynthetic organisms
  作者：Kana Sadaoka、Shigenori Kashimura、Yoshitaka Saga

  DOI：10.1016/j.bmc.2011.05.039

  日期：2011.7

  Reduction of the 7-formyl groups in chlorophyll (Chl) b and its demetalated compound pheophytin (Phe) b was kinetically analyzed by using tert-butylamine-borane complex (t-BuNH2 center dot BH3), and was compared with that of the 3-formyl groups in Chl d and Phe d. Reduction kinetics of the 7-formyl group in Chl b was similar to that in Phe b in dichloromethane containing 5 mM t-BuNH2 center dot BH3. Little difference of the reduction kinetics of the 7-formyl groups between Chl b and Phe b was in sharp contrast to the reduction kinetics of the 3-formyl groups in Chl d and Phe d: the 3-formyl group in Phe d was reduced 5.3-fold faster than that in Chl d. The 7-formyl groups in Chl b and Phe b were reduced more slowly than the 3-formyl groups in Chl d and Phe d, respectively. The difference of the reactivity between the 3- and 7-formyl groups was in line with C-13 NMR measurements of chlorophyllous pigments, in which the chemical shifts of carbon atoms in the 7-formyl groups of Chl b and Phe b were high-field shifted compared with those in the 3-formyl groups of Chl d and Phe d, respectively. These indicate that the 7-formyl groups in chlorophyllous pigments were less reactive for reduction to the corresponding hydroxymethyl groups than the 3-formyl groups due to the difference in electronic states of the formyl groups in the A-and B-rings of the chlorin macrocycle. (C) 2011 Elsevier Ltd. All rights reserved.
• FAECAL MARKERS
  申请人：Lee Michael

  公开号：US20120061588A1

  公开（公告）日：2012-03-15

  Described are methods for analysing an animal carcass, meat obtained therefrom, or product produced by or obtained from an animal for the presence or absence of faecal matter. The methods comprise analysing an animal carcass, meat obtained therefrom, or product produced by or obtained from the animal for the presence or absence of a detectable marker, the presence of the detectable marker being indicative of the presence of faecal matter and the absence of the detectable marker being indicative of the absence of faecal matter, wherein the animal carcass, meat obtained therefrom, or product produced by or obtained from the animal has been obtained from an animal fed a composition comprising a supplement of the detectable marker and/or a precursor thereof. Also described are compositions for feeding to an animal and for use in the methods.
• US8890089B2
  申请人：——

  公开号：US8890089B2

  公开（公告）日：2014-11-18