(3S)-1,7-diphenylheptan-3-ol | 1062083-07-1

• 英文名称: (3S)-1,7-diphenylheptan-3-ol
• CAS: 1062083-07-1
• 化学式: C₁₉H₂₄O
• 分子量: 268.399
• InChiKey: FITFAFMCWGCVDQ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S)-1,7-diphenylheptan-3-ol 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以86%的产率得到[(3S)-1,7-diphenylheptan-3-yl] acetate
  参考文献：
  名称：

  Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation

  摘要：

  Three new diarylheptanoids, a 1: 2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-( 6E)-6-hepten-3- one ( 15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene(9) and 1-(4-hydroxyphenyl)7-phenyl-(4E,6E)-4,6-heptadien-3- one ( 16), and nine known diarylheptanoids, 2, 8, 10 - 12, 14, a 3: 1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ER beta gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an phenolic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1- position of the heptyl chain. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.051
• 作为产物：
  描述：

  (3S)-1,7-diphenyl-(6E)-6-hepten-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以97%的产率得到(3S)-1,7-diphenylheptan-3-ol
  参考文献：
  名称：

  Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation

  摘要：

  Three new diarylheptanoids, a 1: 2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-( 6E)-6-hepten-3- one ( 15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene(9) and 1-(4-hydroxyphenyl)7-phenyl-(4E,6E)-4,6-heptadien-3- one ( 16), and nine known diarylheptanoids, 2, 8, 10 - 12, 14, a 3: 1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ER beta gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an phenolic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1- position of the heptyl chain. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.051

文献信息

• Electrocatalytic Asymmetric Nozaki–Hiyama–Kishi Decarboxylative Coupling: Scope, Applications, and Mechanism
  作者：Yang Gao、Baiyang Jiang、Nathan C. Friede、Arianne C. Hunter、Dylan G. Boucher、Shelley D. Minteer、Matthew S. Sigman、Sarah E. Reisman、Phil S. Baran

  DOI：10.1021/jacs.3c13442

  日期：2024.2.21

  reactions are disclosed herein by employing a Cr-electrocatalytic decarboxylative approach. Using easily accessible aliphatic carboxylic acids (via redox-active esters) as alkyl nucleophile synthons, in combination with aldehydes and enabling additives, chiral secondary alcohols are produced in a good yield with high enantioselectivity under mild reductive electrolysis. This reaction, which cannot be mimicked

  本文通过采用 Cr-电催化脱羧方法公开了第一个通用的对映选择性烷基-Nozaki-Hiyama-Kishi (NHK) 偶联反应。使用易于获得的脂肪族羧酸（通过氧化还原活性酯）作为烷基亲核合成子，与醛和辅助添加剂相结合，在温和的还原电解下以良好的收率和高对映选择性生产手性仲醇。该反应无法使用化学计量的金属或有机还原剂来模拟，可耐受多种官能团，并成功应用于显着简化多种医学相关结构和天然产物的合成。机理研究表明，这种不对称烷基 e-NHK 反应是通过使用催化四（二甲氨基）乙烯来实现的，四（二甲氨基）乙烯充当关键的还原介体，介导 Cr III /手性配体复合物的电还原。