(R,E)-tert-butyl(1-iodooct-1-en-3-yloxy)dimethylsilane | 82510-25-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R,E)-tert-butyl(1-iodooct-1-en-3-yloxy)dimethylsilane
• 英文别名: tert-butyl-[(E,3R)-1-iodooct-1-en-3-yl]oxy-dimethylsilane
• CAS: 82510-25-6
• 化学式: C₁₄H₂₉IOSi
• 分子量: 368.374
• InChiKey: LTLQAJZGKYDIDX-XZHRJIJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R,E)-tert-butyl(1-iodooct-1-en-3-yloxy)dimethylsilane 在 lithium amide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 (R)-(+)-1-辛炔-3-醇
  参考文献：
  名称：

  Practical method for synthesis of optically pure propargylic alcohols

  摘要：

  DOI：

  10.1016/s0040-4039(01)93429-x
• 作为产物：
  描述：

  (R)-(+)-1-辛炔-3-醇 在 咪唑 、 Schwartz's reagent 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 生成 (R,E)-tert-butyl(1-iodooct-1-en-3-yloxy)dimethylsilane
  参考文献：
  名称：

  Rational Design of Antitumor Prostaglandins with High Biological Stability

  摘要：

  Molecular design can overcome the metabolic instability of Delta(7)-PGA(1), while maintaining its antitumor potency. Saturation of the C(13)-C(14) double bond enhances the biological stability but decreases the antiproliferative activity. Configurational inversion of the isomerase-sensitive C(12) stereocenter from the natural S to the unnatural R geometry not only enhances biological stability but also significantly suppresses the growth of the tumor cells. The 12R derivatives markedly increase the induction of p21, a Cdk inhibitor, leading to sharp cell cycle arrest at the G(1) phase at a dose level so low that at this dose Delta(7)-PGA(1) methyl ester scarcely exerts an effect. These conspicuous biological properties lead to long-term suppression of tumor cell growth. The structure-stability relationship demonstrates that the stability of prostaglandins (PGs) is crucially controlled by the C(12) configuration and is unaffected by the geometry of the hydroxy-bearing C(15). The successful design of antitumor PGs resistant to enzymatic metabolism provides a new strategy applicable to creating a useful PG for cancer chemotherapy.

  DOI：

  10.1021/jm9801657

文献信息

• Synthesis of new secoprostaglandins as inducers of platelet aggregation.
  作者：TOSHIO TANAKA、KIYOSHI BANNAI、TAKESHI TORU、TAKEO OBA、NORIAKI OKAMURA、KENZO WATANABE、SEIZI KUROZUMI

  DOI：10.1248/cpb.30.51

  日期：——

  Two series of 8-acetyl-12-hydroxyalkadienoic acids and 14-hydroxy-9-oxoalkadienoic acids, which can be regarded as 11, 12-and 8, 12-secoprostaglandin E2, were synthesized and evaluated for biological activity on platelet function. Key members of each series, 11, 12-and 8, 12-seco-11-norprostaglandin E2, were found to induce platelet aggregation. This effect was inhibited by preincubation of PRP with prostaglandin I2 but was not inhibited by indomethacin.

  合成了两系列的8-乙酰基-12-羟基烯二烯酸和14-羟基-9-氧烯二烯酸，这些化合物可以视为11, 12-和8, 12-秒前列腺素E2，并评估了它们对血小板功能的生物活性。每个系列的关键成员，11, 12-和8, 12-秒-11-去羟基前列腺素E2，被发现能够诱导血小板聚集。该效应被前处理的血小板富血浆与前列腺素I2组合抑制，但并未被吲哚美辛抑制。
• Total Synthesis of Halicholactone and Neohalicholactone
  作者：Jörg Pietruszka、Martina Bischop、Verena Doum、Anja Nordschild née Rieche、Diana Sandkuhl

  DOI：10.1055/s-0029-1217145

  日期：2010.2

  New total syntheses of the marine oxylipins halicholactone and neohalicholactone are presented. The key building blocks were synthesized utilizing chemoenzymatic methods. natural product - total synthesis - enzymes - boron reagents - asymmetric synthesis

  提出了新的海洋氧合素卤代内酯 和新卤代内酯的合成方法 。关键组成部分是利用化学酶法合成的。 天然产物-全合成-酶-硼试剂-不对称合成
• Rational Design of Antitumor Prostaglandins with High Biological Stability
  作者：Masaaki Suzuki、Toshihiro Kiho、Keiichiro Tomokiyo、Kyoji Furuta、Shoji Fukushima、Yoshikazu Takeuchi、Makoto Nakanishi、Ryoji Noyori

  DOI：10.1021/jm9801657

  日期：1998.7.1

  Molecular design can overcome the metabolic instability of Delta(7)-PGA(1), while maintaining its antitumor potency. Saturation of the C(13)-C(14) double bond enhances the biological stability but decreases the antiproliferative activity. Configurational inversion of the isomerase-sensitive C(12) stereocenter from the natural S to the unnatural R geometry not only enhances biological stability but also significantly suppresses the growth of the tumor cells. The 12R derivatives markedly increase the induction of p21, a Cdk inhibitor, leading to sharp cell cycle arrest at the G(1) phase at a dose level so low that at this dose Delta(7)-PGA(1) methyl ester scarcely exerts an effect. These conspicuous biological properties lead to long-term suppression of tumor cell growth. The structure-stability relationship demonstrates that the stability of prostaglandins (PGs) is crucially controlled by the C(12) configuration and is unaffected by the geometry of the hydroxy-bearing C(15). The successful design of antitumor PGs resistant to enzymatic metabolism provides a new strategy applicable to creating a useful PG for cancer chemotherapy.
• ITO, TAKAYORI;OKAMOTO, SENTARO;SATO, FUMIE, TETRAHEDRON LETT., 30,(1989) N0, C. 7083-7086
  作者：ITO, TAKAYORI、OKAMOTO, SENTARO、SATO, FUMIE

  DOI：——

  日期：——
• Takahashi, Taichi; Watanabe, Hidenori; Kitahara, Takeshi, Heterocycles, 2002, vol. 58, p. 99 - 104
  作者：Takahashi, Taichi、Watanabe, Hidenori、Kitahara, Takeshi

  DOI：——

  日期：——