3-(9-acetyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-13,14-dihydro-23H,25H-phorbin-3-yl)-propionic acid 3,7,11,15-tetramethyl-hexadec-2-enyl ester | 128969-77-7

• 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: 3-(9-acetyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-13,14-dihydro-23H,25H-phorbin-3-yl)-propionic acid 3,7,11,15-tetramethyl-hexadec-2-enyl ester
• 英文别名: 3-(9-acetyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-13,14-dihydro-23H,25H-phorbin-3-yl)-propionic acid 3,7,11,15-tetramethyl-hexadec-2-enyl ester
• CAS: 128969-77-7
• 化学式: C₅₃H₇₄N₄O₄
• 分子量: 831.195
• InChiKey: FGWNTULMFPIGQW-RJZJBSTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.77
• 重原子数：
  61.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  117.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(9-acetyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-13,14-dihydro-23H,25H-phorbin-3-yl)-propionic acid 3,7,11,15-tetramethyl-hexadec-2-enyl ester 在 sodium tetrahydroborate 、 硫酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.33h， 生成 methyl bacteriopheophorbide-d
  参考文献：
  名称：

  Asymmetric synthesis of methyl bacteriopheophorbide-d and analogues by stereoselective reduction of the 3-acetyl to the 3-(1-hydroxyethyl) group

  摘要：

  Asymmetric borane-reduction of 3-acetyl-13(1)-oxo-tetrapyrroles (=bacteriochlorin, chlorin and porphyrin) in the presence of a chiral source gave selectively chiral 3-(1-hydroxyethyl)-13(1)-oxo-tetrapyrroles. Oxazaborolidines were effective as chiral auxiliaries. Reduction with (S)-oxazaborolidines led to the (3(1)S)-alcohol as the major product, whose stereoselectivity was the opposite of that in the same asymmetric reduction of usual prochiral ketones ArCOR. The asymmetric reduction of the 3-acetyl group in methyl bacteriopyropheophorbide-a and the 7,8-oxidation afforded 3(1)-epimeric methyl (3(1)S)-bacteriopheophorbide-d (89% de). (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00199-2
• 作为产物：
  描述：

  bacteriopheophytin 在 2,3,5-三甲基吡啶 作用下， 反应 3.0h， 以96%的产率得到3-(9-acetyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-13,14-dihydro-23H,25H-phorbin-3-yl)-propionic acid 3,7,11,15-tetramethyl-hexadec-2-enyl ester
  参考文献：
  名称：

  Asymmetric synthesis of methyl bacteriopheophorbide-d and analogues by stereoselective reduction of the 3-acetyl to the 3-(1-hydroxyethyl) group

  摘要：

  Asymmetric borane-reduction of 3-acetyl-13(1)-oxo-tetrapyrroles (=bacteriochlorin, chlorin and porphyrin) in the presence of a chiral source gave selectively chiral 3-(1-hydroxyethyl)-13(1)-oxo-tetrapyrroles. Oxazaborolidines were effective as chiral auxiliaries. Reduction with (S)-oxazaborolidines led to the (3(1)S)-alcohol as the major product, whose stereoselectivity was the opposite of that in the same asymmetric reduction of usual prochiral ketones ArCOR. The asymmetric reduction of the 3-acetyl group in methyl bacteriopyropheophorbide-a and the 7,8-oxidation afforded 3(1)-epimeric methyl (3(1)S)-bacteriopheophorbide-d (89% de). (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00199-2

文献信息

• Bacteriochlorin aggregates as dopant-free hole-transporting materials for perovskite solar cells
  作者：Na Li、Baoning Wang、Shin-ichi Sasaki、Tsutomu Miyasaka、Gang Chen、Xiao-Feng Wang

  DOI：10.1016/j.orgel.2022.106596

  日期：2022.9

  Organic-inorganic hybrid perovskite solar cells (PSCs) have attracted great interests not only of academic field but also of industrial world toward practical applications in the last decade due to their extremely low production cost and excellent photo-physical properties. Hole-transporting layer (HTL) as an integral component of PSC plays an important role in elevating its performance. In this work

  有机-无机杂化钙钛矿太阳能电池（PSCs）由于其极低的生产成本和优异的光物理性能，在过去十年中不仅引起了学术界的极大兴趣，而且也引起了工业界对实际应用的极大兴趣。空穴传输层 (HTL) 作为 PSC 的组成部分在提升其性能方面发挥着重要作用。在这项工作中，制备了五种以不同 C17-丙酸残基为特征的细菌叶绿素-a衍生物及其J-类型聚集体作为 PSC 的 HTL 进行了研究。已证实引入的 C17-丙酸酯侧链的性质对主要染料单元的电化学性质（如电子吸收光谱和能级）的影响可以忽略不计。然而，链特征的不同亲油性、亲水性或疏水性会影响每种染料组分的溶解度，从而导致其聚集膜的不同表面形态，如 AFM 观察所揭示的。此外，通过旋涂法制备的五种固体薄膜作为 HTL 显示出不同的电荷提取和传输能力，这得到了光致发光光谱和电化学阻抗谱测量结果的支持，并被认为是 PSC 性能不同的根本原因。