diethyl (3-carbethoxybenzyl)phosphonate | 79026-14-5

• 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: diethyl (3-carbethoxybenzyl)phosphonate
• 英文别名: Ethyl 3-((diethoxyphosphoryl)methyl)benzoate；ethyl 3-(diethoxyphosphorylmethyl)benzoate
• CAS: 79026-14-5
• 化学式: C₁₄H₂₁O₅P
• 分子量: 300.292
• InChiKey: MIZUTTUNNHKCOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (3-carbethoxybenzyl)phosphonate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 氯仿 、 甲苯 为溶剂， 20.0~40.0 ℃ 、450.0 kPa 条件下， 反应 103.0h， 生成 1,3-bis(3-(bromomethyl)phenethyl)benzene
  参考文献：
  名称：

  Windisch; Vo̿gtle; Nieger, Advanced Synthesis and Catalysis, 2000, vol. 342, # 7, p. 642 - 653

  摘要：

  DOI：
• 作为产物：
  描述：

  间甲基苯甲酸 在 偶氮二异丁腈 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 diethyl (3-carbethoxybenzyl)phosphonate
  参考文献：
  名称：

  Windisch; Vo̿gtle; Nieger, Advanced Synthesis and Catalysis, 2000, vol. 342, # 7, p. 642 - 653

  摘要：

  DOI：

文献信息

• Synthesis and Structure-Activity Relationships of Stilbene Retinoid Analogs Substituted with Heteroaromatic Carboxylic Acids
  作者：Richard L. Beard、Diana F. Colon、Samuel J. Gillett、Elizabeth Henry、Deborah K. Marler、Tae Song、Lydia Denys、Michael E. Garst、Taghreed Arefieg

  DOI：10.1021/jm00015a004

  日期：1995.7

  currently known: retinoic acid receptors (RAR alpha,beta,and gamma) and retinoid X receptors (RXR alpha,beta,and gamma). Stilbene retinoid analogs of retinoic acid (RA), such as (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)prope n-1- yl]benzoic acid (TTNPB, 1) and (E)-4-[2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)pro pen-1- yl]benzoic acid (3-methyl-TTNPB, 2), display

  类维生素A通过激活一系列核受体引发生物反应。目前已知属于两个家族的六个类视黄醇受体：视黄酸受体（RARα，β和γ）和类视黄醇X受体（RXRα，β和γ）。视黄酸（RA）的二苯乙烯类视黄醇类似物，例如（E）-4- [2-（5,6,7,8-四氢-5,5,8,8-四甲基-2-萘基）丙烷n-1 -yl]苯甲酸（TTNPB，1）和（E）-4- [2-（5,6,7,8-四氢-3,5,5,8,8-五甲基-2-萘基）pro pen- 1-基]苯甲酸（3-甲基-TTNPB，2）显示不同的RAR和RXR活性，具体取决于萘环C3处的取代基。我们在此报告2的苯甲酸酯部分的结构修饰，从而导致具有更高RXR选择性的类似物以及具有泛激动剂（同时激活RAR和RXR受体）的类似物，分析赋予受体选择性的结构特征，并描述合成这些类似物的立体选择方法。通过测试具有不同受体激活谱的代表性实例，检测与RAR和RXR受体相关的生物学活性
• Conformationally restricted retinoids
  作者：Marcia I. Dawson、Peter D. Hobbs、Krzysztof Derdzinski、Rebecca L. S. Chan、John Gruber、Wanru Chao、Saundra Smith、Richard W. Thies、Leonard J. Schiff

  DOI：10.1021/jm00377a022

  日期：1984.11

  A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter. These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic acid (1) held in a planar cisoid conformation by inclusion in an aromatic ring. The meta-substituted analogue 3 of 4-[(E)-2-methyl-4-(2,6,6-trimethylcyclohexenyl)-1,3-butadienyl+ ++]benzoic acid (2) was far less active than 2 in both assays. In contrast, the vinyl homologue of 2 (4) and the 7,8-dihydro and 7,8-methano analogues (5 and 6) had activity comparable to that of 2. Analogues of 4-[(E)-2-(1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-6-naphthyl)propenyl] benzoic acid (7) were also screened. Replacement of the tetrahydronaphthalene ring of 7 by a benzonorbornenyl group (9) significantly reduced activity, as did removal of the vinylic methyl group from 9 (10). Replacement of the propenyl group of 9 by a cyclopropane ring (12) also reduced activity. Replacement of the tetrahydronaphthalene ring of 7 by 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran and -benzothiopyran rings (13 and 14) also decreased activity. Inclusion of the 7,9 double bond system of 1 in an aromatic ring (15 and 16) reduced activity, whereas inclusion of the 5,7 double bond system in an aromatic ring enhanced activity (7 and 19). Inclusion of the 11,13 and 9,11,13 double bond systems in aromatic rings (2 and 18) also reduced activity below that of 1. Retinoic acid, 7, 13, 14, and 19 inhibited papilloma tumor formation in mice. Toxicity testing indicated that 7 was more toxic than 1, 13, 14, and 19, 19 was more toxic than 1, and 13 and 14 were less toxic than 1.
• US4766235A
  申请人：——

  公开号：US4766235A

  公开（公告）日：1988-08-23
• US5234946A
  申请人：——

  公开号：US5234946A

  公开（公告）日：1993-08-10
• Windisch; VoÌ¿gtle; Nieger, Advanced Synthesis and Catalysis, 2000, vol. 342, # 7, p. 642 - 653
  作者：Windisch、VoÌ¿gtle、Nieger、Lahtinen、Rissanen

  DOI：——

  日期：——