tributyl(((4-methoxybenzyl)oxy)methyl)stannane | 120385-24-2

• 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: tributyl(((4-methoxybenzyl)oxy)methyl)stannane
• 英文别名: p-Methoxybenzyloxymethyltributyltin；tributyl-[(4-methoxyphenyl)methoxymethyl]stannane
• CAS: 120385-24-2
• 化学式: C₂₁H₃₈O₂Sn
• 分子量: 441.242
• InChiKey: WGRDXBHKVQDMJW-UHFFFAOYSA-N

物化性质

• 沸点：
  439.1±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tributyl(((4-methoxybenzyl)oxy)methyl)stannane 在 正丁基锂 、 仲丁基锂 、 二甲基亚砜 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成 4-[3-[(4-methoxyphenyl)methoxy]prop-1-en-2-yl]-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole
  参考文献：
  名称：

  Cyclopent[a]anthraquinones as DNA-Intercalating Agents with Covalent Bond Formation Potential:  Synthesis and Biological Activity

  摘要：

  A series of mitomycin C (MMC) analogues, namely cyclopentanthraquinone derivatives, were synthesized via Diels-Alder cyclization of naphthoquinone with 1-vinylcyclopent-1-enes. These new compounds are planar structures, like MMC, and bear an aziridine ring and a methyl carbamate side chain. After bioreduction, they are anticipated to be capable of intercalating into double-stranded DNA and bind covalently. Structure-activity relationships were studied. Of these compounds, 2,3-aziridino-4-[[(methylamino)carbonyl]methyl]cyclopent[a]anthracene-6,11-dione (4) was shown to have inhibitory activity against several leukemic and solid tumor cell lines. Mice (BDF1) bearing Lewis lung adenocarcinoma were treated with 4 and MMC (ip, QD x 5). At a dose of 30.0 mg/kg, compound 4 was as effective as MMC (0.8 mg/kg). Compound 4 appears to be less toxic than MMC. DNA unwinding assay indicated that 4 is able to intercalate into DNA double strands and is also a topoisomerase II inhibitor.

  DOI：

  10.1021/jm950881y
• 作为产物：
  描述：

  三丁基(碘甲基)锡烷 、 4-甲氧基苄醇 在 potassium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 以83%的产率得到tributyl(((4-methoxybenzyl)oxy)methyl)stannane
  参考文献：
  名称：

  通过电化学生成的氧离子的碎裂形成碳离子†

  摘要：

  在亲核试剂的存在下，可以利用电化学产生的氧鎓离子的碎片来形成低氧化电位的碳正离子。该概念的应用已证明可用于通过苯乙烯基甲基醚的阳极氧化生成的碳正离子的烯丙基化。

  DOI：

  10.1039/c8ob01339j

文献信息

• Formal Synthesis of Pseudolaric Acid B
  作者：Naoki Mori

  DOI：10.1055/s-0039-1690829

  日期：2020.6

  A formal synthesis of pseudolaric acid B, a diterpene isolated from the root bark of Pseudolarix kaempferi Gordon (Pinaceae), to Trost’s synthetic intermediate was achieved in 17 steps from a known ketone. Key features of this synthesis include a Claisen rearrangement and iodoetherification to construct quaternary stereocenters and ring-closing metathesis to form the seven-membered ring.

  从已知的酮中通过 17 个步骤实现了假落叶酸 B（一种从 Pseudolarix kaempferi Gordon（松科）的根皮中分离的二萜）到 Trost 合成中间体的正式合成。该合成的主要特征包括克莱森重排和碘醚化以构建四元立体中心和闭环复分解以形成七元环。
• Synthetic studies towards the phomactins. Concise syntheses of the tricyclic furanochroman and the oxygenated bicyclo[9.3.1]pentadecane ring systems in phomactin A
  作者：Kevin M Foote、Christopher J Hayes、Matthew P John、Gerald Pattenden

  DOI：10.1039/b307985f

  日期：——

  A concise synthesis of the tricyclic furanochroman unit 3 found in the PAF antagonist phomactin A (1) isolated from the marine fungus Phoma sp., is described. In complementary studies, a variety of synthetic routes towards the bicyclo[9.3.1]pentadecane ring system 4 in phomactin A were explored. These studies culminated in a synthesis of the substituted ring system 79 containing all the carbon atoms

  描述了从海洋真菌Phoma sp。分离出的PAF拮抗剂phomactin A（1）中发现的三环呋喃喃喃单元3的简明合成。在补充研究中，探索了多种在光蛋白A中合成双环[9.3.1]十五烷环系统4的合成途径。这些研究最终合成了取代环系统79，该取代环系统包含所有的碳原子和所有必要的氧中心，以形成光蛋白A本身。
• Total Synthesis of Neodolastane Diterpenes Trichoaurantianolides C and D
  作者：David R. Williams、Paul T. Gladen、Joseph R. Pinchman

  DOI：10.1021/acs.joc.5b00355

  日期：2015.6.5

  The first total synthesis of trichoaurantianolides C and D is described. An enantiocontrolled pathway leads to rapid construction of the tricyclic carbon skeleton and establishes the trans-dimethyl geometry of the quaternary bridgehead carbons via a reductive cyclization. Application of the π-allyl Stille cross-coupling leads to a nonracemic allylic alcohol as a prerequisite for the introduction of

  描述了天花香豆素内酯C和D的第一全合成。对映体控制的途径导致三环碳骨架的快速构建并建立反式-季二桥头碳的-二甲基几何结构通过还原环化。π-烯丙基斯蒂勒交叉偶联的应用导致非外消旋烯丙基醇作为在环庚烷体系中引入不对称性的先决条件。为了从普通的三环中间体中制备不饱和四氢呋喃基环，已经研究了两种策略。这些努力揭示了许多未曾预料到的反应性问题，以及对于新型酰基辅酶重排以及手性α-羟基酮的消除和环脱水的重要立体化学要求。导致合成完成的关键反应包括异丙烯基锂TMEDA配合物的立体选择性加成和二氧化硒的简便化学选择性氧化。
• Method of using 4-amino 6-substituted mycophenolic acid and derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05525602A1

  公开（公告）日：1996-06-11

  The disclosed derivatives of mycophenolic acid are therapeutic agents advantageous in the treatment of disease states indicated for mycophenolic acid and/or mycophenolate mofetil and other immunosuppressant agents.

  所披露的霉酚酸衍生物是治疗疾病状态中的治疗剂，适用于霉酚酸和/或麻酮酯酸酯以及其他免疫抑制剂。
• The Total Synthesis of Eleutherobin
  作者：Xiao-Tao Chen、Samit K. Bhattacharya、Bishan Zhou、Clare E. Gutteridge、Thomas R. R. Pettus、Samuel J. Danishefsky

  DOI：10.1021/ja990215c

  日期：1999.7.1

  The total synthesis of the title compound (1), starting with (R)-(−)-α-phellandrene (6), has been accomplished. The synthesis rigorously proves the relative stereochemical relationship of the diterpenoid and carbohydrate domains of eleutherobin. Key reactions included a Nozaki−Kishi ring closure to produce a furanophane (see 37 → 38), a pyranose to furanose transposition (see 50 → 47), and a novel

  以(R)-(-)-α-水芹烯(6)开始的标题化合物(1)的全合成已经完成。该合成严格地证明了五七甙的二萜和碳水化合物结构域的相对立体化学关系。关键反应包括 Nozaki-Kishi 环闭合以产生呋喃烷（参见 37 → 38）、吡喃糖至呋喃糖转座（参见 50 → 47）和用于连接两个域的新型氧碳糖苷化（参见 58 → 87）。