4-[3-[1,3]-Dioxolan-2-yl-propenyl)benzoic acid methyl ester | 667909-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[3-[1,3]-Dioxolan-2-yl-propenyl)benzoic acid methyl ester
• 英文别名: methyl 4-[3-(1,3-dioxolan-2-yl)prop-1-enyl]benzoate
• CAS: 667909-36-6
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: LSTFELUTIXKSSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[3-[1,3]-Dioxolan-2-yl-propenyl)benzoic acid methyl ester 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以91%的产率得到methyl 4-[3-(1,3-dioxolan-2-yl)propyl]benzoate
  参考文献：
  名称：

  Structural determinants for histamine H1 affinity, hERG affinity and QTc prolongation in a series of terfenadine analogs

  摘要：

  In the late 1980's reports linking the non-sedating antihistamines terfenadine and astemizole with torsades de pointes, a form of ventricular tachyarrhythmia that can degenerate into ventricular fibrillation and sudden death, appeared in the clinical literature. A substantial body of evidence demonstrates that the arrhythmogenic effect of these cardiotoxic antihistamines, as well as a number of structurally related compounds, results from prolongation of the QT interval due to suppression of specific delayed rectifier ventricular K+ currents via blockade of the hERG-IKr channel. In order to better understand the structural requirements for hERG and H-1 binding for terfenadine, a series of analogs of terfenadine has been prepared and studied in both in vitro and in vivo hERG and H-1 assays. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.047
• 作为产物：
  描述：

  2-(1,3-二氧戊环-2-基)乙基三苯基溴化磷 、 对甲酰基苯甲酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以90%的产率得到4-[3-[1,3]-Dioxolan-2-yl-propenyl)benzoic acid methyl ester
  参考文献：
  名称：

  Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring

  摘要：

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.

  DOI：

  10.1021/jo034767w

文献信息

• Biologically active acylated amino acid derivatives
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US05723459A1

  公开（公告）日：1998-03-03

  The present invention relates to novel compounds which possess a broad range of useful biological activities. These compounds can maintain, increase, or restore sensitivity of cells to therapeutic or prophylactic agents. They can also suppress, modify, or significantly reduce an immune response, including an autoimmune response in a mammal. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well-suited for treatment of multi-drug resistant cells, for prevention of the development of multi-drug resistance, for use in multi-drug resistant cancer therapy, and for prevention or treatment of graft rejection and various autoimmune diseases.

  本发明涉及具有广泛有用生物活性的新化合物。这些化合物可以维持、增加或恢复细胞对治疗或预防剂的敏感性。它们还可以抑制、修改或显著减少哺乳动物的免疫反应，包括自身免疫反应。本发明还涉及包含这些化合物的药物组合物。本发明的化合物和药物组合物特别适用于治疗多药耐药细胞，预防多药耐药的发展，用于多药耐药癌症治疗，以及预防或治疗移植排斥和各种自身免疫疾病。
• Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring
  作者：Hiroaki Ohno、Mitsuaki Okumura、Shin-ichiro Maeda、Hiroki Iwasaki、Ryutaro Wakayama、Tetsuaki Tanaka

  DOI：10.1021/jo034767w

  日期：2003.10.1

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.
• Structural determinants for histamine H1 affinity, hERG affinity and QTc prolongation in a series of terfenadine analogs
  作者：Robert Aslanian、John J. Piwinski、Xiaohong Zhu、Tony Priestley、Steve Sorota、Xiao-Yi Du、Xue-Song Zhang、Robbie L. McLeod、Robert E. West、Shirley M. Williams、John A. Hey

  DOI：10.1016/j.bmcl.2009.07.047

  日期：2009.9

  In the late 1980's reports linking the non-sedating antihistamines terfenadine and astemizole with torsades de pointes, a form of ventricular tachyarrhythmia that can degenerate into ventricular fibrillation and sudden death, appeared in the clinical literature. A substantial body of evidence demonstrates that the arrhythmogenic effect of these cardiotoxic antihistamines, as well as a number of structurally related compounds, results from prolongation of the QT interval due to suppression of specific delayed rectifier ventricular K+ currents via blockade of the hERG-IKr channel. In order to better understand the structural requirements for hERG and H-1 binding for terfenadine, a series of analogs of terfenadine has been prepared and studied in both in vitro and in vivo hERG and H-1 assays. (C) 2009 Elsevier Ltd. All rights reserved.