(5-((tert-butyldiphenylsilyl)oxy)pentyl)iodotriphenylphosphane

• 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: (5-((tert-butyldiphenylsilyl)oxy)pentyl)iodotriphenylphosphane
• 英文别名: [5-(tert-butyldiphenylsilyloxy)pentyl]triphenylphosphonium iodide；5-[Tert-butyl(diphenyl)silyl]oxypentyl-triphenylphosphanium;iodide
• 化学式: C₃₉H₄₄OPSi*I
• 分子量: 714.742
• InChiKey: APPBSZKXQVXUGW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-((tert-butyldiphenylsilyl)oxy)pentyl)iodotriphenylphosphane 在 palladium on activated charcoal chromium dichloride 、 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 碘苯二乙酸 、 四丁基氟化铵 、 氢气 、 碘 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 68.74h， 生成 Acetic acid (1S,3R,4S,6R,8S,9R,10R)-9-(2-acetoxy-ethyl)-4-[1,3]dithian-2-ylmethyl-1-hydroxy-3-methoxy-10-((E)-oct-6-enyl)-2-oxa-tricyclo[6.4.0.0^4,12]dodec-11-en-6-yl ester
  参考文献：
  名称：

  （-）-CP-263,114的全合成研究

  摘要：

  烷氧基由于其在分子转化中的显着化学性质而在有机合成中具有广泛的应用。本研究表明，有两种类型的烷氧基自由基（伯基和叔基）选择性地进行脱氢和β断裂，从而形成（-）-CP-263,114（1）的关键结构要素。通过烷氧基自由基转化，然后安装C19-C25（CP编号）侧链和桥连双缩醛单元，获得官能化的CP前体2。

  DOI：

  10.1021/jo048681u
• 作为产物：
  描述：

  4-(t-butyldiphenylsiloxy) pentyl-p-toluene sulfonate 在 sodium iodide 作用下， 以 丙酮 、 苯 为溶剂， 反应 12.0h， 生成 (5-((tert-butyldiphenylsilyl)oxy)pentyl)iodotriphenylphosphane
  参考文献：
  名称：

  Synthesis of the tetracyclic ABCE ring subunit I, bearing the 13-membered azacycle, of manzamine A

  摘要：

  The tetracyclic ABCE ring, which bears the crucial 13-membered azacycle, of manzamine A has been synthesized through the corresponding bicyclic BC ring subunit as a promising synthetic intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00479-7

文献信息

• New Metal-Free One-Pot Synthesis of Substituted Allenes from Enones
  作者：Meng Tang、Chun-An Fan、Fu-Min Zhang、Yong-Qiang Tu、Wen-Xue Zhang、Ai-Xia Wang

  DOI：10.1021/ol802445p

  日期：2008.12.18

  A new metal-free, one-pot synthesis of substituted allenes from enones was discovered for the first time, in which a tertiary amine as a base was found to be an effective promoter in such novel transformations. The present synthetic protocol proceeded readily with high compatibility of sensitive functional groups, and it provides a new efficient way to access a series of synthetically important allenes

  首次发现了一种新的无金属，一锅法从烯酮合成取代的丙二烯的方法，其中发现叔胺为碱是这种新型转化的有效促进剂。本合成方案易于进行，且与敏感官能团具有高度相容性，并且它提供了一种无需使用金属试剂或催化剂即可获得一系列合成上重要的烯的有效途径。
• Amphimic acids and related long-chain fatty acids as DNA topoisomerase I inhibitors from an Australian sponge, Amphimedon sp.: Isolation, structure, synthesis, and biological evaluation
  作者：Takayuki Nemoto、Go Yoshino、Makoto Ojika、Youji Sakagami

  DOI：10.1016/s0040-4020(97)10099-0

  日期：1997.12

  fatty acids have been isolated from an Australian sponge, Amphimedon sp., as human DNA topoisomerase I inhibitors. Three of them, amphimic acids A (1)-C (3), are unusual fatty acids possessing a cyclopropylidene group, and one is a new C30 fatty acid 4. Their structures were elucidated by spectroscopic analysis and chemical degradation. The enantioselective synthesis of 1 was carried out to determine

  从澳大利亚海绵Amphimedon sp。中分离出了几种C 27 – C 30不饱和脂肪酸，作为人类DNA拓扑异构酶I抑制剂。其中三个，两性酸A（1）-C（3），是具有环亚丙基的不常见脂肪酸，一个是新的C 30脂肪酸4。通过光谱分析和化学降解阐明了它们的结构。进行1的对映选择性合成以确定两性酸的绝对构型。对这些天然产物和合成衍生物评估了DNA拓扑异构酶I的抑制活性。
• Syntheses and Biological Activities of Danicalipin A Derivatives
  作者：Taiki Umezawa、Takeshi Maeda、Takuya Akiyama、Nurcahyo Iman Prakoso、Jakia Jerin Mehjabin、Tatsufumi Okino、Fuyuhiko Matsuda

  DOI：10.1002/cbdv.202300400

  日期：2023.6

  Synthesis of three derivatives of danicalipin A, tetrachloride, trisulfate and a fluorescent probe was achieved through Wittig reaction strategy. Toxicity of the derivatives against brine shrimp (Artemia salina) as also investigated to provide useful information for the biological activity; i) less chloride derivative showed similar toxicity to danicalipin A, ii) the amphiphilic property, a characteristic

  通过Wittig反应策略合成了丹卡利平A的三种衍生物、四氯化物、三硫酸盐和荧光探针。还研究了衍生物对丰年虾（Artemia salina）的毒性，为生物活性提供有用的信息；i) 较少的氯化物衍生物表现出与丹尼卡利平 A 相似的毒性，ii) 两亲性（丹尼卡利平 A 的特征）至关重要，因为三硫酸盐​​显着降低了毒性，以及 iii) 荧光衍生物保留了丹尼卡利平 A 的丰年虾毒性。
• A Remarkably Useful Sulfur Bridge as Synthetic Lever in an Approach to Javanicin B
  作者：Claude Spino、Amélie Dion

  DOI：10.3987/com-16-s(s)58

  日期：——

  A concise and efficient synthesis of a non-racemic advanced intermediate to the quassinoid javanicin B is disclosed. The strategy is centred on a triple diene-transmissive Diels-Alder cycloaddition to form the four rings of javanicin B. A sulfur bridge plays several crucial roles allowing an intramolecular cycloaddition to occur with complete stereoselectivity, controlling the stereochemical outcome of another cycloaddition, and transforming into a pivotal electrophile for the introduction of a particularly hindered methyl group.
• Attempts directed towards the synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C
  作者：G.V.M. Sharma、J. Janardhan Reddy、K. Laxmi Reddy

  DOI：10.1016/j.tetlet.2006.07.043

  日期：2006.9

  Attempts to synthesise iso-cladospolide-B, cladospolide-B and cladospolide-C resulted in macrolides 1, 2 and 4 along with butenolide 3. Of the three stereogenic centres, the C-4/C-5 vic-diol was obtained from tartaric acid and D-glucose, while the C-11 stereocentre was created by Jacobsen's method. (c) 2006 Elsevier Ltd. All rights reserved.